Publication Cover
Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 9
463
Views
49
CrossRef citations to date
0
Altmetric
Synthetic Communications Reviews

Nickel catalysis: six membered heterocycle syntheses

Pages 1103-1133 | Received 31 Dec 2018, Accepted 07 Jan 2019, Published online: 08 Feb 2019

References

  • (a) Balaban, A. T.; Oniciu, D. C.; Katritzky, A. R. Aromaticity as a Cornerstone of Heterocyclic Chemistry. Chem. Rev. 2004, 104, 2777. (b) Majumdar, P.; Pati, A.; Patra, M.; Behera, R. K.; Behera, A. K. Acid Hydrazides, Potent Reagents for Synthesis of Oxygen-, Nitrogen-, and/or Sulfur-Containing Heterocyclic Rings. Chem. Rev. 2014, 114, 2942. (c) Reddy, C. R.; Ranjan, R.; Kumaraswamy, P.; Motati, D. R.; Grée, R. 1-Aryl Propargylic Alcohols as Handy Synthons for the Construction of Heterocycles and Carbocycles. COC. 2014, 18, 2603. (d) Uredi, D.; Motati, D. R.; Watkins, E. B. A Unified Strategy for the Synthesis of β-Carbolines, γ-Carbolines, and Other Fused Azaheteroaromatics under Mild, Metal-Free Conditions. Org. Lett. 2018, 20, 6336. (e) Motati, D. R.; Fronczek, F. R.; Watkins, E. B. Org. Lett. 2016, 18, 5620. (f) Nagesh, N.; Raju, G.; Srinivas, R.; Ramesh, P.; Reddy, M. D.; Reddy, C. R. A Dihydroindolizino Indole Derivative Selectively Stabilizes G-quadruplex DNA and Down-Regulates c-MYC Expression in Human Cancer Cells. Biochimica Biophysica Acta. 2015, 1850, 129. (g) Motati, D. R.; Kobori, H.; Mori, T.; Wu, J.; Kawagishi, H.; Watkins, E. B. J. Nat. Prod. 2017, 80, 2561. (h) Das, A.; Kulkarni, A.; Torok, B. Green Chem. 2012, 14, 17. (i) Motati, D. R.; Blanton, A. N.; Watkins, E. B. J. Org. Chem. 2017, 82, 5080. (j) Motati, D. R.; Watkins, E. B. J. Org. Chem. 2015, 80, 11447.
  • (a) Martins, M.; Cunico, W.; Pereira, C.; Sinhorin, A.; Flores, A.; Bonacorso, H.; Zanatta, N. 4-Alkoxy-1,1,1-Trichloro-3-Alken-2-ones: Preparation and Applications in Heterocyclic Synthesis. COS 2004, 1, 391. (b) Liu, Q.; Wu, L.; Jackstell, R.; Beller, M. Nature Commun. 2015, 6, 5933. (c) Kaur, N. Palladium-Catalyzed Approach to the Synthesis of S-Heterocycles. Catal. Rev. 2015, 57, 478. (d) Kaur, N. Mercury-catalyzed Synthesis of Heterocycles. Synth. Commun. 2018, 48, 2715. (e) Kaur, N. Photochemical Irradiation: Seven and Higher Membered O-Heterocycles. Synth. Commun. 2018, 48, 2935. (f) Kaur, N. Synthesis of Seven and Higher Membered Nitrogen Containing Heterocycles Using Photochemical Irradiation. Synth. Commun. 2018, 48, 2815.
  • (a) Domling, A. Chem. Rev. 2006, 106, 17. (b) Reddy, C. R.; Valleti, R. R.; Motati, D. R. J. Org. Chem. 2013, 78, 6495. (c) Reddy, C. R.; Dilipkumar, U.; Motati, D. R. Org. Lett. 2014, 16, 3792. (d) Raji Reddy, C.; Panda, S. A.; Reddy, M. D. Aza-Annulation of Enynyl Azides: A New Approach to Substituted Pyridines. Org. Lett. 2015, 17, 896. (e) Venkateshwarlu, R.; Chinnababu, B.; Ramulu, U.; Purushotham Reddy, K.; Damoder Reddy, M.; Sowjanya, P.; Venkateswara Rao, P.; Aravind, S. Synthesis and Biological Evaluation of (−)-Kunstleramide and Its Derivatives. Med. Chem. Commun. 2017, 8, 394. (f) Reddy, C. R.; Motati, D. R.; Srikanth, B.; Prasad, K. R. Org. Biomol. Chem. 2011, 9, 6027.
  • (a) Kaur, N. Benign Approaches for the Microwave-assisted Synthesis of Five-membered 1,2- N, N-Heterocycles. J. Heterocyclic Chem. 2015, 52, 953. (b) Kaur, N. Methods for Metal and Non-Metal Catalyzed Synthesis of Six-Membered Oxygen Containing Poly-Heterocycles. COS. 2017, 14, 531. (c) Kaur, N. Curr. Org. Synth. 2017, 14, 972. (d) Kaur, N. Ionic Liquids: Promising but Challenging Solvents for the Synthesis of NHeterocycles. Mini Rev. Org. Chem. 2017, 14, 3. (e) Kaur, N. Metal Catalysts for the Formation of Six-Membered N-Polyheterocycles. Synth. React. Inorg. Met. Org. Nano-Met. Chem. 2016, 46, 983. (f) Kaur, N. Applications of Gold Catalysts for the Synthesis of Five-membered O-Heterocycles. Inorg. Nano-Met. Chem. 2017, 47, 163. (g) Orru, R. V. A.; de Greef, M. Recent Advances in Solution-PhaseMulticomponent Methodology for the Synthesis of HeterocyclicCompounds. ChemInform 2003, 34, 1471. (h) Kaur, N. Ruthenium Catalysis in Six-membered O-heterocycles Synthesis. Synth. Commun. 2018, 48, 1551. (i) Kaur, N. Green Synthesis of Three- to Five-Membered O-heterocycles Using Ionic Liquids. Synth. Commun. 2018, 48, 1588. (j) Kaur, N. Ultrasound-assisted Green Synthesis of Five-Membered O- and S- Heterocycles. Synth. Commun. 2018, 48, 1715. (k) Kaur, N. Photochemical Mediated Reactions in Five-Membered O- heterocycles Synthesis. Synth. Commun. 2018, 48, 2119. (l) Kaur, N. Ruthenium Catalyzed Synthesis of Five-Membered O-Heterocycles. Inorg. Chem. Commun. 2019, 99, 82.
  • (a) Kaur, N. Palladium-Catalyzed Approach to the Synthesis of Five-membered O-Heterocycles. Inorg. Chem. Commun. 2014, 49, 86. (b) Kaur, N.; Kishore, D. Nitrogen-Containing Six-Membered Heterocycles: Solid-Phase Synthesis. Synth. Commun. 2014, 44, 1173. (c) Kaur, N.; Kishore, D. Solid-Phase Synthetic Approach toward the Synthesis of Oxygen-Containing Heterocycles. Synth. Commun. 2014, 44, 1019. (d) Kaur, N. Microwave-Assisted Synthesis of Five-Membered O-Heterocycles. Synth. Commun. 2014, 44, 3483. (e) Kaur, N. Microwave-Assisted Synthesis of Five-Membered O,N-Heterocycles. Synth. Commun. 2014, 44, 3509. (f) Kaur, N. Microwave-Assisted Synthesis of Five-Membered O,N,N-Heterocycles. Synth. Commun. 2014, 44, 3229. (g) Kaur, N. Synthesis of Six- and Seven-membered Heterocycles under Ultrasound Irradiation. Synth. Commun. 2018, 48, 1235. (h) Kaur, N. Photochemical Reactions as Key Steps in Five-membered N- heterocycle Synthesis. Synth. Commun. 2018, 48, 1259. (i) Kaur, N. Solid-phase Synthesis of Sulfur Containing Heterocycles. J. Sulfur Chem. 2018, 39, 544.
  • (a) Kaur, N. Metal Catalysts: applications in Higher-membered N-heterocycles Synthesis. J. Iran. Chem. Soc. 2015, 12, 9. (b) Kaur, N. Insight into Microwave-Assisted Synthesis of Benzo Derivatives of Five-Membered N,N-Heterocycles. Synth. Commun. 2015, 45, 1269. (c) Kaur, N. Synthesis of Fused Five-Membered N,N-Heterocycles Using Microwave Irradiation. Synth. Commun. 2015, 45, 1379. (d) Kaur, N. Microwave-Assisted Synthesis of Seven-Membered S-Heterocycles. Synth. Commun. 2014, 44, 3201. (e) Kaur, N. Six-Membered N-Heterocycles: Microwave-Assisted Synthesis. Synth. Commun. 2015, 45, 1. (f) Kaur, N. Polycyclic Six-Membered N-Heterocycles: Microwave-Assisted Synthesis. Synth. Commun. 2015, 45, 35. (g) Kaur, N. Copper Catalysts in the Synthesis of Five-membered N-Polyheterocycles. COS. 2018, 15, 940. (h) Kaur, N. Recent Developments in the Synthesis of Nitrogen Containing Five-membered Polyheterocycles Using Rhodium Catalysts. Synth. Commun. 2018, 48, 2457.
  • (a) Kaur, N. Microwave-Assisted Synthesis: Fused Five-Membered N-Heterocycles. Syn. Commun. 2015, 45, 789. (b) Kaur, N. Six-Membered Heterocycles with Three and Four N-Heteroatoms: Microwave-Assisted Synthesis. Synth. Commun. 2015, 45, 151. (c) Kaur, N. Application of Microwave Irradiation in the Synthesis of Fused Six-Membered Heterocycles with N-Heteroatom. Synth. Commun. 2015, 45, 173. (d) Kaur, N. Microwave-Assisted Synthesis of Fused Polycyclic Six-Membered N-Heterocycles. Synth. Commun. 2015, 45, 273. (e) Kaur, N. Review of Microwave-Assisted Synthesis of Benzo-Fused Six-Membered N,N-Heterocycles. Synth. Commun. 2015, 45, 300. (f) Kaur, N.; Kishore, D. Synthetic Strategies Applicable in the Synthesis of Privileged Scaffold: 1,4-Benzodiazepine. Synth. Commun. 2014, 44, 1375.
  • (a) Kaur, N. Environmentally Benign Synthesis of Five-Membered 1,3- N,N-Heterocycles by Microwave Irradiation. Syn. Commun. 2015, 45, 909. (b) Kaur, N. Advances in Microwave-Assisted Synthesis for Five-Membered N-Heterocycle Synthesis. Synth. Commun. 2015, 45, 432. (c) Kaur, N. Microwave-Assisted Synthesis of Five-membered S-Heterocycles. J. Iranian Chem. Soc. 2014, 11, 523. (d) Kaur, N. Review on the Synthesis of Six-Membered N,N-Heterocycles by Microwave Irradiation. Synth. Commun. 2015, 45, 1145. (e) Kaur, N. Greener and Expeditious Synthesis of Fused Six-Membered N,N-Heterocycles Using Microwave Irradiation. Synth. Commun. 2015, 45, 1493. (f) Kaur, N. Applications of Microwaves in the Synthesis of Polycyclic Six-Membered N,N-Heterocycles. Synth. Commun. 2015, 45, 1599. (g) Kaur, N. Synthesis of Five-Membered N,N,N- and N,N,N,N-Heterocyclic Compounds: Applications of Microwaves. Synth. Commun. 2015, 45, 1711.
  • (a) Patil, N. T.; Yamamoto, Y.; Coinage Metal-Assisted Synthesis of Heterocycles. Chem. Rev. 2008, 108, 3395. (b) Reddy, C. R.; Motati, D. R.; Srikanth, B.; Phosphine-mediated Cascade Reaction of Azides with MBH-acetates of Acetylenic Aldehydes to Substituted Pyrroles: a Facile Access to N-fused Pyrrolo-Heterocycles. Org. Biomol. Chem. 2012, 10, 4280. (c) Reddy, C. R.; Krishna, G.; Motati, D. R.; Synthesis of Substituted 3-furanoates from MBH-acetates of Acetylenic Aldehydes via Tandem Isomerization-Deacetylation-Cycloisomerization: Access to Elliott’s Alcohol. Org. Biomol. Chem. 2014, 12, 1664. (d) Motati, D. R.; Uredi, D.; Watkins, E. B.; A General Method for the Metal-free, Regioselective, Remote C-H Halogenation of 8-substituted Quinolines. Chem. Sci. 2018, 9, 1782. (e) Sudina, P. R.; Motati, D. R.; Seema, A.; Stereocontrolled Total Synthesis of Nonenolide. J. Nat. Prod. 2018, 81, 1399. (f) Reddy, C. R.; Dilipkumar, U.; Motati, D. R.; Rao, N. N. Total Synthesis and Revision of the Absolute Configuration of Seimatopolide B. Org. Biomol. Chem. 2013, 11, 3355.
  • (a) Kaur, N. Role of Microwaves in the Synthesis of Fused Five-Membered Heterocycles with Three N-Heteroatoms. Syn. Commun. 2015, 45, 403. (b) Kaur, N. Recent Impact of Microwave-Assisted Synthesis on Benzo Derivatives of Five-Membered N-Heterocycles. Synth. Commun. 2015, 45, 539. (c) Kaur, N.; Kishore, D. Microwave-Assisted Synthesis of Seven- and Higher-Membered N-Heterocycles. Synth. Commun. 2014, 44, 2577. (d) Kaur, N.; Kishore, D. Microwave-Assisted Synthesis of Six-Membered S-Heterocycles. Synth. Commun. 2014, 44, 2615. (e) Kaur, N.; Kishore, D. Microwave-Assisted Synthesis of Seven- and Higher-Membered O-Heterocycles. Synth. Commun. 2014, 44, 2739.
  • (a) Alberico, D.; Scott, M. E.; Lautens, M.; Aryl − Aryl Bond Formation by Transition-Metal-Catalyzed Direct Arylation. Chem. Rev. 2007, 107, 174. (b) Kaur, N.; Curr. Organocatal. 2017, 4. 122. (c) Reddy, C. R.; Motati, D. R.; J. Org. Chem. 2014, 7, 106. (d) Raju, G.; Srinivas, R.; Motati, D. R.; Reddy, C. R.; Nagesh, N. Nucleosides, Nucleotides & Nucleic Acids 2014, 33, 489.
  • Dick, A. R.; Sanford, M. S. Transition Metal Catalyzed Oxidative Functionalization of Carbon-hydrogen Bonds. Tetrahedron 2006, 62, 2439. DOI: 10.1016/j.tet.2005.11.027.
  • (a) Kaur, N.; Palladium Catalysts: Synthesis of Five-Membered N-Heterocycles Fused with Other Heterocycles. Catal. Rev. 2015, 57, 1. (b) Kaur, N.; Kishore, D. Microwave-Assisted Synthesis of Six-Membered O,O-Heterocycles. Synth. Commun. 2014, 44, 3082. (c) Kaur, N.; Kishore, D. Microwave-Assisted Synthesis of Six-Membered O-Heterocycles. Synth. Commun. 2014, 44, 3047. (d) Diez-Gonzalez, S.; Marion, N.; Nolan, S. P. Chem. Rev. 2009, 109, 3612.
  • Zeni, G.; Larock, R. C. Synthesis of Heterocycles via Palladium-catalyzed Oxidative Addition. Chem. Rev. 2006, 106, 4644.
  • Jimenez-Gonzalez, L.; Garcia-Munoz, S.; Alvarez-Corral, M.; Munoz-Dorado, M.; Rodriguez-Garcia, I. Chem. Eur. J. 2006, 12, 8762.
  • Li, Z.; He, C. Recent Advances in Silver-Catalyzed Nitrene, Carbene, and Silylene-Transfer Reactions. Eur. J. Org. Chem. 2006, 2006, 4313. DOI: 10.1002/ejoc.200500602.
  • Takahashi, T.; Tsai, F.-Y.; Li, Y.; Wang, H.; Kondo, Y.; Yamanaka, M.; Nakajima, K.; Kotora, M. Selective Preparation of Pyridines, pyridones, and Iminopyridines from Two Different Alkynes via Azazirconacycles. J. Am. Chem. Soc. 2002, 124, 5059.
  • McCormick, M. M.; Duong, H. A.; Zuo, G.; Louie, J. A Nickel-Catalyzed Route to Pyridines. J. Am. Chem. Soc. 2005, 127, 5030.
  • Duong, H. A.; Cross, M. J.; Louie, J. Nickel-Catalyzed Cycloaddition of Alkynes and isocyanates. J. Am. Chem. Soc. 2004, 126, 11438.
  • Sato, Y.; Sawaki, R.; Mori, M. Dramatic Influence on the Olefinic Geometry in the Nickel(0)-Catalyzed Coupling Reaction of 1,3-Dienes and Aldehydes Using N-Heterocyclic Carbene as a Ligand. Organometallics 2001, 20, 5510.
  • Ho, C. Y.; Jamison, T. F. Highly Selective Coupling of Alkenes and Aldehydes Catalyzed by [Ni(NHC){P(OPh)3}]: Synergy between a Strong Sigma Donor and a Strong pi acceptor. Angew. Chem. Int. Ed. Engl. 2007, 46, 782.
  • Schleicher, K. D.; Jamison, T. F. Nickel-Catalyzed Synthesis of Acrylamides from Alpha-Olefins and Isocyanates. Org. Lett. 2007, 9, 875.
  • Zuo, G.; Louie, J. Highly Active Nickel Catalysts for the Isomerization of Unactivated Vinyl Cyclopropanes to cyclopentenes. Angew. Chem. Int. Ed. Engl. 2004, 43, 2277.
  • Campora, J.; de la Tabla, L. O.; Palma, P.; Alvarez, E.; Lahoz, F.; Mereiter, K. Organometallics 2006, 25, 3314. DOI: 10.1021/om060439l.
  • Li, W. F.; Sun, H. M.; Chen, M. Z.; Shen, Q.; Zhang, Y. Synthesis and Catalytic Activity of Neutral Salicylaldiminato Nickel(II) complexes Bearing a Single N-heterocyclic Carbene Ligand. J. Organomet. Chem. 2008, 693, 2047. DOI: 10.1016/j.jorganchem.2008.03.005.
  • MacKinnon, A. L.; Baird, M. C. The Synthesis and X-ray Structure of trans-NiCl2(1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene)2; Attempts to Polymerize Olefins Utilizing a Nickel(II) Complex of a Sterically Demanding N-heterocyclic Carbene. J. Organomet. Chem. 2003, 683, 114. DOI: 10.1016/S0022-328X(03)00458-3.
  • Kuhl, S.; Schneider, R.; Fort, Y. Transfer Hydrogenation of Imines Catalyzed by a Nickel(0)/NHC Complex. Organometallics 2003, 22, 4184. DOI: 10.1021/om034046n.
  • Yang, X. Z.; Hall, M. B. The Catalytic Dehydrogenation of Ammonia-Borane Involving an Unexpected Hydrogen Transfer to Ligated Carbene and Subsequent Carbon-hydrogen activation. J. Am. Chem. Soc. 2008, 130, 1798.
  • Davis, J. L.; Arndtsen, B. A. Comparison of Imine to Olefin Insertion Reactions: Generation of Five- and Six-Membered Lactams via a Nickel-Mediated CO, Olefin, CO, Imine Insertion Cascade. Organometallics 2011, 30, 1896. DOI: 10.1021/om1011566.
  • Hoberg, H.; Oster, B. W. J. Organomet. Chem 1982, 234, C35.
  • Hoberg, H.; Oster, B. W. Synthesis 1982, 4, 324.
  • Hoberg, H.; Oster, B. W. Nickelaverbindungen Als Zwischenkomplexe Der [2 + 2+2′]-Cycloaddition Von Alkinen Mit Isocyanaten zu 2-Pyridonen. J. Organomet. Chem. 1983, 252, 359. DOI: 10.1016/S0022-328X(00)99836-X.
  • Moore, L. R.; Vicic, D. A. A Heterogeneous-catalyst-based, microwave-assisted Protocol for the Synthesis of 2,2'-bipyridines. Chem. Asian J. 2008, 3, 1046.
  • Varela, J. A.; Saá, C. Construction of Pyridine Rings by Metal-mediated [2 + 2 + 2] cycloaddition. Chem. Rev. 2003, 103, 3787.
  • Nakao, Y. Synthesis 2011, 20, 3209. DOI: 10.1055/s-0030-1260212.
  • Sakal, S. B.; Shelke, K. F.; Shingate, B. B.; Shingare, M. S. Tetrahedron Lett. 2009, 50, 1754. DOI: 10.1016/j.tetlet.2009.01.140.
  • Hugel, H. M. Molecules 2009, 14, 4936.
  • Korivi, R. P.; Cheng, C. Highly Efficient Synthesis of Isoquinolines via Nickel-catalyzed Annulation of 2-iodobenzaldimines with Alkynes: Evidence for Dual Pathways of Alkyne insertion. Org. Lett. 2005, 7, 5179.
  • Miura, T.; Yamauchi, M.; Murakami, M. Synthesis of 1(2H)-isoquinolones by the Nickel-Catalyzed Denitrogenative Alkyne Insertion of 1,2,3-benzotriazin-4(3H)-ones. Org. Lett. 2008, 10, 3085.
  • Duong, H. A.; Louie, J. A Nickel(0) Catalyzed Cycloaddition of Alkynes and Isocyanates That Affords Pyrimidine-Diones. Tetrahedron 2006, 62, 7552. DOI: 10.1016/j.tet.2006.03.119.
  • Lu, G.; Malinakova, H. C. Regio- and Diastereoselective Insertion of Allenes into Stable Oxapalladacycles with a Metal-bonded Stereogenic Carbon. Preparation of Contiguously Substituted 3,4-dihydro-2H-1-benzopyrans. J. Org. Chem. 2004, 69, 8266.
  • Miyake, Y.; Nishibayashi, Y.; Uemura, S. Synlett 2008, 12, 1747. DOI: 10.1055/s-2008-1077903.
  • Yamauchi, M.; Morimoto, M.; Miura, T.; Murakami, M. Enantioselective Synthesis of 3,4-dihydroisoquinolin-1(2H)-ones by Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-benzotriazin-4(3H)-ones With Allenes. J. Am. Chem. Soc. 2010, 132, 54.
  • Miura, T.; Morimoto, M.; Yamauchi, M.; Murakami, M. Nickel-Catalyzed Denitrogenative Annulation Reactions of 1,2,3-Benzotriazin-4(3 H)-Ones with 1,3-Dienes and Alkenes. J. Org. Chem. 2010, 75, 5359. DOI: 10.1021/jo1008756.
  • Ho, C.-Y. Cyanative Alkene-aldehyde Coupling: Ni(0)-NHC-Et2AlCN Mediated Chromanol Synthesis with High Cis-selectivity at Room temperature. Chem. Commun. (Camb.) Camb. 2010, 46, 466.
  • Sato, Y.; Nishimata, T.; Mori, M. Asymmetric Synthesis of Isoindoline and Isoquinoline Derivatives Using Nickel(0)-Catalyzed [2 + 2 + 2] Cocyclization. J. Org. Chem. 1994, 59, 6133. DOI: 10.1021/jo00100a003.
  • Takahashi, T.; Tsai, F.; Kotora, M. Selective Formation of Substituted Pyridines from Two Different Alkynes and a Nitrile: Novel Coupling Reaction of Azazirconacyclopentadienes with Alkynes. J. Am. Chem. Soc. 2000, 122, 4994. DOI: 10.1021/ja000474y.
  • Tekavec, T. N.; Zuo, G.; Simon, K.; Louie, J. An in Situ Approach for Nickel-Catalyzed Cycloaddition. J. Org. Chem. 2006, 71, 5834.
  • Stolley, R. M.; Maczka, M. T.; Louie, J. Nickel-Catalyzed [2 + 2+2] Cycloaddition of Diynes and Cyanamides. Eur. J. Org. Chem. 2011, 2011, 3815.
  • Montgomery, J. Nickel-catalyzed Cyclizations, Couplings, and Cycloadditions Involving Three Reactive components. Acc. Chem. Res. 2000, 33, 467.
  • Tang, X. Q.; Montgomery, J. Nickel-Catalyzed Preparation of Bicyclic Heterocycles: Total Synthesis of (+)-Allopumiliotoxin 267A, (+)-Allopumiliotoxin 339A, and (+)-Allopumiliotoxin 339B. J. Am. Chem. Soc. 2000, 122, 6950. DOI: 10.1021/ja001440t.
  • Chiusoli, G. P.; Pallini, L.; Terenghi, G. Cobalt Catalysed Cyclo-codimerization of Dipropargylamines and Nitriles to Dihydropyrrolopyridines. Transition Met. Chem. 1983, 8, 250. DOI: 10.1007/BF00620704.
  • Chiusoli, G. P.; Pallini, L.; Terenghi, G. Chem. Abstr. 1984, 100, 121035.
  • Dzhemilev, U. M.; Selimov, F. A.; Tolstikov, G. A. ARKIVOC. 2001, ix, 85.
  • Negishi, E.-I.; Holmes, S. J.; Tour, J. M.; Miller, J. A.; Cederbaum, F. E.; Swanson, D. R.; Takahashi, T. Metal-Promoted Cyclization. 19. Novel Bicyclization of Enynes and Diynes Promoted by Zirconocene Derivatives and Conversion of Zirconabicycles into Bicyclic Enones via Carbonylation. J. Am. Chem. Soc. 1989, 111, 3336. DOI: 10.1021/ja00191a035.
  • Lounasmaa, M.; Karvinen, E.; Koskinen, A.; Jokela, R. Novel Applications of the Modified Polonovski reaction-IX. Tetrahedron 1987, 43, 2135. DOI: 10.1016/S0040-4020(01)86795-8.
  • Fujikara, S.; Inoue, M.; Utimoto, K.; Nozaki, H. Tetrahedron Lett. 1984, 25, 1999. DOI: 10.1016/S0040-4039(01)90096-6.
  • Hua, D. H.; Bharathi, S. N.; Panangadan, J. A. K.; Tsujimoto, A. Stereoselective Additions of Chiral.alpha.-Sulfinyl Ketimine Anions to Ene Esters. Asymmetric Syntheses of Indolo[2,3-a]quinolizidine and Yohimban Alkaloids. J. Org. Chem. 1991, 56, 6998. DOI: 10.1021/jo00025a011.
  • Wenkert, E.; Chang, C.-J.; Chawla, H. P. S.; Cochran, D. W.; Hagaman, E. W.; King, J. C.; Orito, K. General Methods of Synthesis of Indole Alkaloids. 14. Short Routes of Construction of Yohimboid and Ajmalicinoid Alkaloid Systems and Their Carbon-13 Nuclear Magnetic Resonance Spectral Analysis. J. Am. Chem. Soc. 1976, 98, 3645. DOI: 10.1021/ja00428a044.
  • Wender, P. A.; Smith, T. E. Transition Metal-Catalyzed Intramolecular [4 + 2] Cycloadditions: A Novel Method for the Assembly of Nitrogen Heterocycles and Its Application to Yohimban Alkaloid Synthesis. J. Org. Chem. 1996, 61, 824. DOI: 10.1021/jo9519827.
  • Ma, J.; Yin, W.; Zhou, H.; Cook, J. M. Total Synthesis of the Opioid Agonistic Indole Alkaloid Mitragynine and the First Total Syntheses of 9-methoxygeissoschizol and 9-methoxy-Nb-methylgeissoschizol. Org. Lett. 2007, 9, 3491.
  • Ma, J.; Yin, W.; Zhou, H.; Liao, X.; Cook, J. M. General Approach to the Total Synthesis of 9-methoxy-substituted Indole Alkaloids: Synthesis of Mitragynine, as Well as 9-methoxygeissoschizol and 9-methoxy-N(b)-methylgeissoschizol. J. Org. Chem. 2009, 74, 264.
  • (a) Insuasty, B. A.; Torres, H.; Quiroga, J.; Abonia, R.; Rodriguez, R.; Nogueras, M.; Sánchez, A.; Saitz, C.; Alvarez, S. L.; Zacchino, S. A. J. Chil. Chem. Soc. 2006, 51, 927. (b) Dawood, K. M.; Abdel-Wahab, B. F. Arkivoc. 2010, i, 333.
  • Cross, B.; Williams, P. J.; Woodall, R. E. The Preparation of Phenazines by the Cyclisation of 2-Nitrodiphenylamines. J. Chem. Soc, C. 1971, 0, 2085. DOI: 10.1039/j39710002085.
  • Murdock, K. C.; Lin, Y.; Thomas, J. P.; Lang, S. A. Antitubercular 2,8-bis(alkylaminomethyl)phenazines. J. Med. Chem. 1978, 21, 403.
  • Clemo, G. R.; Daglish, A. F. 307. The Phenazine Series. Part VIII. The Constitution of the Pigment of Chromobacterium Iodinum. J. Chem. Soc. 1950, 1950, 1481. DOI: 10.1039/jr9500001481.
  • Skorianetz, W.; Kovats, E. S. Eine Neue Synthese Von 3,6-Dialkyl-1,2,4,5-Tetrazinen. Hca. 1971, 54, 1922. DOI: 10.1002/hlca.19710540721.
  • Larsen, C.; Binderup, E.; Møller, J.; Cyvin, S. J.; Hagen, G. Mass Spectrometry of 1,2,4,5-Tetrazines. Acta Chem. Scand. 1967, 21, 2855. DOI: 10.3891/acta.chem.scand.21-2855.
  • Hu, W. X.; Xu, F. Synthesis, Structures of Some Unsymmetrical 3,6-disubstituted-1,2,4,5-Tetrazines. J. Heterocycl. Chem. 2008, 45, 1745. DOI: 10.1002/jhet.5570450628.
  • Karver, M. R.; Weissleder, R.; Hilderbrand, S. A. Angew. Chem. 2012, 124, 944; Angew. Chem. Int. Ed. 2012, 51, 920.
  • Lang, S. A.; Johnson, B. D.; Cohen, E. Novel Synthesis of Unsymmetrically Substituted s -Tetrazines. J. Heterocycl. Chem. 1975, 12, 1143. DOI: 10.1002/jhet.5570120612.
  • Yang, J.; Karver, M. R.; Li, W.; Sahu, S.; Devaraj, N. K. Metal-Catalyzed One-Pot Synthesis of Tetrazines Directly from Aliphatic Nitriles and Hydrazine. Angew. Chem. Int. Ed. Engl. 2012, 51, 5222.
  • Blackman, M. L.; Royzen, M.; Fox, J. M. Tetrazine Ligation: Fast Bioconjugation Based on Inverse-Electron-Demand Diels-Alder Reactivity. J. Am. Chem. Soc. 2008, 130, 13518.
  • Devaraj, N. K.; Weissleder, R.; Hilderbrand, S. A. Tetrazine-Based Cycloadditions: Application to Pretargeted Live Cell imaging. Bioconjug. Chem. 2008, 19, 2297.
  • Rossin, R.; Verkerk, P. R.; van den Bosch, S. M.; Vulders, R. C.; Verel, I.; Lub, J.; Robillard, M. S. Angew. Chem. 2010, 122, 3447.; Angew. Chem. Int. Ed. 2010, 49, 3375.
  • Devaraj, N. K.; Upadhyay, R.; Haun, J. B.; Hilderbrand, S. A.; Weissleder, R. Angew. Chem. 2009, 121, 7147.; Angew. Chem. Int. Ed. 2009, 48, 7013.
  • Karver, M. R.; Weissleder, R.; Hilderbrand, S. A. Synthesis and Evaluation of a Series of 1,2,4,5-tetrazines for Bioorthogonal conjugation. Bioconjug. Chem. 2011, 22, 2263.
  • Haun, J. B.; Devaraj, N. K.; Hilderbrand, S. A.; Lee, H.; Weissleder, R. Bioorthogonal Chemistry Amplifies Nanoparticle Binding and Enhances the Sensitivity of Cell Detection. Nat. Nanotechnol. 2010, 5, 660.
  • Hofmann, K. A.; Ehrhart, O. Einwirkung Von Hydrazin Auf Dicyandiamid. Ber. Dtsch. Chem. Ges. 1912, 45, 2731. DOI: 10.1002/cber.191204502185.
  • Muller, E.; Herrdegen, L. J. Prakt. Chem. 1921, 102, 113. DOI: 10.1002/prac.19211020402.
  • Curtius, T.; Hess, A. Einwirkung Von Hydrazin Auf m-Cyanbenzoesäure. J. Prakt. Chem. 1930, 125, 40. DOI: 10.1002/prac.19301250103.
  • Bowie, R. A.; Neilson, D. G.; Watson, K. M.; Gardner, M. D.; Ridd, V.; Mahmood, S. J. Chem. Soc, Perkin Trans. 1. 1972, 1, 2395. DOI: 10.1039/p19720002395.
  • Abdel, N.O.; Kira, M.A.; Tolba, M.N. A Direct Synthesis of Dihydrotetrazines. Tetrahedron Lett. 1968, 9, 3871. DOI: 10.1016/S0040-4039(01)99123-3.
  • Pinner, A. Ueber Die Einwirkung Von Hydrazin Auf Imidoäther. Ber. Dtsch. Chem. Ges. 1893, 26, 2126. DOI: 10.1002/cber.189302602188.
  • Audebert, P.; Sadki, S.; Miomandre, F.; Clavier, G.; Vernieres, M. C.; Saoud, M.; Hapiot, P. Synthesis of New Substituted Tetrazines: Electrochemical and Spectroscopic Properties. New J. Chem. 2004, 28, 387. DOI: 10.1039/B310737J.
  • Oxley, P.; Partridge, M. W.; Short, W. F. 209. Amidines. Part VII. Preparation of Amidines from Cyanides, aluminium Chloride, and Ammonia or Amines. J. Chem. Soc. 1947, 0, 1110. DOI: 10.1039/jr9470001110.
  • Siegl, W. O. Metal Ion Activation of Nitriles. Syntheses of 1,3-bis(arylimino)Isoindolines. J. Org. Chem. 1977, 42, 1872. DOI: 10.1021/jo00431a011.
  • Demko, Z. P.; Sharpless, K. B. Preparation of 5-substituted 1H-tetrazoles from Nitriles in Water. J. Org. Chem. 2001, 66, 7945.
  • Wang, J. F.; Xu, F.; Cai, T.; Shen, Q. Addition of Amines to Nitriles Catalyzed by Ytterbium Amides: An Efficient One-step Synthesis of Monosubstituted N-arylamidines. Org. Lett. 2008, 10, 445.
  • Kukushkin, V. Y.; Pombeiro, A. J. L. Additions to Metal-Activated Organonitriles. Chem. Rev. 2002, 102, 1771.
  • Rousselet, G.; Capdevielle, P.; Maumy, M. Copper(I)-Induced Addition of Amines to Unactivated Nitriles: The First General One-step Synthesis of Alkyl Amidines. Tetrahedron Lett. 1993, 34, 6395. DOI: 10.1016/0040-4039(93)85054-Z.
  • Zajac, W. W.; Siuda, J. F.; Nolan, M. J.; Santosusso, T. M. J. Org. Chem. 1971, 36, 3539.
  • Lim, C. L.; Pyo, S. H.; Kim, T. Y.; Yim, E. S.; Han, B. H. Bull. Korean Chem. Soc. 1995, 16, 374.
  • Hertweck, C. Copper(II) Triflate in Organic Synthesis. J. Prakt. Chem. 2000, 342, 316. DOI: 10.1002/(SICI)1521-3897(200003)342:3<316::AID-PRAC316>3.3.CO;2-J.
  • Kotora, M.; Ishikawa, M.; Tsai, F.-Y.; Takahashi, T. Halogen-Dependent Coupling Reaction of Alkynes with (Z)-3-halopropenoates Catalyzed by Nickel. Tetrahedron 1999, 55, 4969. DOI: 10.1016/S0040-4020(99)00182-9.
  • Kirsch, G.; Hesse, S.; Comel, A. Synthesis of Five- and Six-Membered Heterocycles through Palladium- Catalyzed Reactions. COS. 2004, 1, 47.
  • Kim, H.; Lee, C. Nickel-Catalyzed Reductive Cyclization of Organohalides. Org. Lett. 2011, 13, 2050.
  • Tsuda, T.; Kiyoi, T.; Miyane, T.; Saegusa, T. Nickel(0)-Catalyzed Reaction of Diynes with Aldehydes. J. Am. Chem. Soc. 1988, 110, 8570. DOI: 10.1021/ja00233a057.
  • Miller, K.; Jamison, T. F. Highly Regioselective, Catalytic Asymmetric Reductive Coupling of 1,3-enynes and Ketones. Org. Lett. 2005, 7, 3077.
  • Tekavec, T. N.; Tekevac, T. N.; Louie, J. Nickel-Catalyzed Cycloaddition of Unsaturated Hydrocarbons and Carbonyl compounds. Org. Lett. 2005, 7, 4037.
  • Tekavec, T. N.; Louie, J. Nickel-Catalyzed Cycloadditions of Unsaturated Hydrocarbons, Aldehydes, and Ketones. J. Org. Chem. 2008, 73, 2641.
  • Kajita, Y.; Kurahashi, T.; Matsubara, S. Nickel-Catalyzed Decarbonylative Addition of Anhydrides to Alkynes. J. Am. Chem. Soc. 2008, 130, 17226. DOI: 10.1021/ja806569h.
  • Kajita, Y.; Kurahashi, T.; Matsubara, S. Nickel-Catalyzed Decarbonylative Addition of Phthalimides to Alkynes. J. Am. Chem. Soc. 2008, 130, 6058.
  • Inami, T.; Baba, Y.; Kurahashi, T.; Matsubara, S. Nickel-Catalyzed Cycloadditions of Thiophthalic Anhydrides with Alkynes. Org. Lett. 2011, 13, 1912.
  • Nakai, K.; Kurahashi, T.; Matsubara, S. Nickel-Catalyzed Cycloaddition of o-arylcarboxybenzonitriles and Alkynes via Cleavage of Two Carbon-Carbon σ bonds. J. Am. Chem. Soc. 2011, 133, 11066.
  • Chattopadhyay, B.; Gevorgyan, V. Transition-Metal-Catalyzed Denitrogenative Transannulation: Converting Triazoles into Other Heterocyclic Systems. Angew. Chem. Int. Ed. Engl. 2012, 51, 862.
  • Louie, J.; Gibby, J. E.; Farnworth, M. V.; Tekavec, T. N. Efficient Nickel-Catalyzed [2 + 2 + 2] Cycloaddition of CO2 and Diynes. J. Am. Chem. Soc. 2002, 124, 15188.
  • Inoue, Y.; Itoh, Y.; Hashimoto, H. Oligomerization of 3-HEXYNE by Nickel(0) Complexes Under CO2. Incorporation of CO2 and Novel Cyclotrimerization. Chem. Lett. 1978, 7, 633. DOI: 10.1246/cl.1978.633.
  • Inoue, Y.; Itoh, Y.; Hashimoto, H. Incorporation of Carbon Dioxide in Alkyne Oligomerization Catalyzed by Nickel(0) Complexes. Formation of Substituted 2-Pyrones. Chem. Lett. 1977, 6, 855. DOI: 10.1246/cl.1977.855.
  • Inoue, Y.; Itoh, Y.; Kazama, H.; Hashimoto, H. Reaction of Dialkyl-Substituted Alkynes with Carbon Dioxide Catalyzed by Nickel(0) Complexes. Incorporation of Carbon Dioxide in Alkyne Dimers and Novel Cyclotrimerization of the Alkynes. Bcsj. 1980, 53, 3329. DOI: 10.1246/bcsj.53.3329.
  • Tsuda, T.; Sumiya, R.; Saegusa, T. Nickel-Mediated Cycloaddition of Diynes with Carbon Dioxide to Bicyclic α-Pyrones. Synth. Commun. 1987, 17, 147. DOI: 10.1080/00397918708057214.
  • Tsuda, T.; Morikawa, S.; Sumiya, R.; Saegusa, T. Nickel(0)-Catalyzed Cycloaddition of Diynes and Carbon Dioxide to Give Bicyclic.alpha.-Pyrones. J. Org. Chem. 1988, 53, 3140. DOI: 10.1021/jo00249a003.
  • Tsuda, T.; Morikawa, S.; Saegusa, T. Functionalized Phosphine Ligands in Transition Metal-Catalysed Organic Synthesis. Nickel(0)-Catalysed Cycloaddition of Terminally Unsubstituted Diynes and Carbon Dioxide to Bicyclic 2-Pyrones. J. Chem. Soc. Chem. Commun. 1989, 1, 9.
  • Tsuda, T.; Hasegawa, N.; Saegusa, T. Nickel(0)-Catalysed Novel co-oligomerization of Ethoxy(trimethylsilyl)ethyne with Carbon Dioxide to 4,6-diethoxy-3-[1-ethoxy-2,2-bis(trimethylsilyl)vinyl]-5(trimethylsilyl)-2-Pyrone. J. Chem. Soc. Chem. Commun 1990, 13, 945.
  • Tsuda, T.; Morikawa, S.; Hasegawa, N.; Saegusa, T. Nickel(0)-Catalyzed Cycloaddition of Silyl Diynes with Carbon Dioxide to Silyl Bicyclic.alpha.-Pyrones. J. Org. Chem. 1990, 55, 2978. DOI: 10.1021/jo00296a083.
  • Tsuda, T.; Maruta, K.; Kitaike, T. Nickel(0)-Catalyzed Alternating Copolymerization of Carbon Dioxide with Diynes to Poly(2-pyrones). J. Am. Chem. Soc. 1992, 114, 1498. DOI: 10.1021/ja00030a065.
  • Tekavec, T. N.; Arif, A.; Louie, J. Regioselectivity in Nickel(0) Catalyzed Cycloadditions of Carbon Dioxide with Diynes. Tetrahedron 2004, 60, 7431. DOI: 10.1016/j.tet.2004.06.025.
  • Nakamura, I.; Yamamoto, Y. Transition-Metal-Catalyzed Reactions in Heterocyclic synthesis. Chem. Rev. 2004, 104, 2127.
  • Tamao, K.; Kobayashi, K.; Ito, Y. Nickel(0)-Promoted Cyclization of Enynes with Isocyanides: A New Route to Polycyclic Cyclopentenone Skeletons. J. Am. Chem. Soc. 1988, 110, 1286. DOI: 10.1021/ja00212a045.
  • Sachdeva, H.; Dwivedi, D.; Bhattacharjee, R. R.; Khaturia, S.; Saroj, R. J. Chem. 2013, 2013, 10. DOI: 10.1155/2013/606259.
  • Kamijo, S.; Dudley, G. B. Tandem Nucleophilic Addition/Fragmentation Reactions and Synthetic Versatility of Vinylogous Acyl Triflates. J. Am. Chem. Soc. 2006, 128, 6499.
  • Christoffers, J.; Scharl, H.; Frey, W.; Baro, A. Transformation of an Optically Active Decahydro-6-isoquinolone Scaffold: Perfect Felkin-Anh Diastereoselectivity. Org. Lett. 2004, 6, 1171.
  • Mohanakrishnan, A. K.; Amaladass, P. Synthesis of 1,3-diaryl Benzo[c]Thiophenes. Tetrahedron Lett. 2005, 46, 4225. DOI: 10.1016/j.tetlet.2005.04.048.
  • Gomez Arrayas, R.; Cabrera, S.; Carretero, J. C. Copper-Catalyzed Anti-Stereocontrolled Ring-Opening of Azabicyclic Alkenes with Grignard Reagents. Org. Lett. 2005, 7, 219.
  • Ohmiya, H.; Yorimitsu, H.; Oshima, K. Cobalt(diamine)-Catalyzed Cross-Coupling Reaction of Alkyl Halides With Arylmagnesium Reagents: Stereoselective Constructions of Arylated Asymmetric Carbons and Application to Total Synthesis of AH13205. J. Am. Chem. Soc. 2006, 128, 1886.
  • Ohmiya, H.; Wakabayashi, K.; Yorimitsu, H.; Oshima, K. Cobalt-Catalyzed Cross-Coupling Reactions of Alkyl Halides with Aryl Grignard Reagents and Their Application to Sequential Radical Cyclization/Cross-Coupling Reactions. Tetrahedron 2006, 62, 2207. DOI: 10.1016/j.tet.2005.12.013.
  • Peters, A.; Branda, N. R. Electrochemically Induced Ring-Closing of Photochromic 1,2-Dithienylcyclopentenes. Chem. Commun. 2003, 8, 954. DOI: 10.1039/b211378c.
  • Collis, G. E.; Burrell, A. K.; Scott, S. M.; Officer, D. L. Toward Functionalized Conducting Polymers: Synthesis and Characterization of Novel beta-(styryl)terthiophenes. J. Org. Chem. 2003, 68, 8974.
  • Satou, T.; Sakai, T.; Kaikawa, T.; Takimiya, K.; Otsubo, T.; Aso, Y. α,ω-Bis(quinquethienyl)alkanes as a π-Dimer Model of Polythiophene. Org. Lett. 2004, 6, 997. DOI: 10.1021/ol0499396.
  • Liu, X.-M.; Xu, J.; He, C. Synthesis, Optical, and Electrochemical Properties of Conjugated Oligomers Derived from 4-bromo-4′-(n-butyl)-2,2′-Biphenyl. Tetrahedron Lett. 2004, 45, 1507. DOI: 10.1016/j.tetlet.2003.12.016.
  • Pepitone, M. F.; Eaiprasertsak, K.; Hardaker, S. S.; Gregory, R. V. Synthesis of Bis[(3,4-ethylenedioxy)thien-2-yl]-Substituted Benzenes. Tetrahedron Lett. 2004, 45, 5637. DOI: 10.1016/j.tetlet.2004.05.114.
  • Chinchilla, R.; Najera, C.; Yus, M. ARKIVOC. 2007, x, 152.
  • Coppola, G. M. The Chemistry of Isatoic Anhydride. Synthesis 1980, 1980, 505. DOI: 10.1055/s-1980-29110.
  • Kappe, T.; Stadlbauer, W. Adv. Heterocycl. Chem. 1981, 28, 127.
  • Thurston, D. E.; Murty, V. S.; Langley, D. R.; Jones, G. B. O-Debenzylation of a Pyrrolo[2,1-c][1,4]benzodiazepine in the Presence of a Carbinolamine Functionality: Synthesis of DC-81. Synthesis 1990, 1990, 81. DOI: 10.1055/s-1990-26795.
  • Coppola, G.; Damon, R. E.; Hardtmann, G. E. 4-Hydroxy-2-quinolinone-3-carboxylic Acids. Synthesis 1981, 1981, 391. DOI: 10.1055/s-1981-29464.
  • Wang, T.; Lui, A. S.; Cloudsdale, I. S. A Novel Route to Pyrrolo[2,1-c][1,4]benzodiazepin-5-ones. Formal Total Synthesis of (±)-DC-81. Org. Lett. 1999, 1, 1835. DOI: 10.1021/ol991100g.
  • Dai, W.-M.; Wang, X.; Ma, C. Microwave-Assisted One-Pot Regioselective Synthesis of 2-alkyl-3,4-dihydro-3-oxo-2H-1,4-Benzoxazines. Tetrahedron 2005, 61, 6879. DOI: 10.1016/j.tet.2005.04.072.
  • Miura, T.; Yamauchi, M.; Kosaka, A.; Murakami, M. Angew. Chem. 2010, 122, 5075; Angew. Chem. Int. Ed. 2010, 49, 4955.
  • Pawlas, J.; Nakao, Y.; Kawatsura, M.; Hartwig, J. F. A General Nickel-Catalyzed Hydroamination of 1,3-dienes by Alkylamines: Catalyst Selection, Scope, and Mechanism. J. Am. Chem. Soc. 2002, 124, 3669.
  • Grigg, R.; Liu, A.; Shaw, D.; Suganthan, S.; Woodall, D. E.; Yoganathan, G. Synthesis of Quinol-4-ones and Chroman-4-ones via a Palladium-Catalysed Cascade Carbonylation-Allene Insertion. Tetrahedron Lett. 2000, 41, 7125.
  • Tang, W.; Zhang, X. Angew. Chem. 2002, 114, 1682; Angew. Chem. Int. Ed. 2002, 41, 1612.
  • Burk, M. J. C2-symmetric Bis(phospholanes) and Their Use in Highly Enantioselective Hydrogenation Reactions. J. Am. Chem. Soc. 1991, 113, 8518. DOI: 10.1021/ja00022a047.
  • Alcock, N. W.; Brown, J. M.; Hulmes, D. I. Synthesis and Resolution of 1-(2-diphenylphosphino-1-naphthyl)isoquinoline; a P,N Chelating Ligand for Asymmetric Catalysis. Tetrahedron: Asymmetry 1993, 4, 743. DOI: 10.1016/S0957-4166(00)80183-4.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.