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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 49, 2019 - Issue 23
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ARTICLES

A facile approach to 6-amino-2H-pyrano[2,3-g]isoquinolin-2-ones via a sequential Sonogashira coupling of 6-cyanoumbelliferone triflate and annulations with amines

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Pages 3301-3310 | Received 30 Jun 2019, Published online: 13 Sep 2019

References

  • Medina, F. G.; Marrero, J. G.; Macías-Alonso, M.; González, M. C.; Córdova-Guerrero, I.; Teissier García, A. G.; Osequeda-Robles, S. Coumarin Heterocyclic Derivatives: Chemical Synthesis and Biological Activity. Nat. Prod. Rep. 2015, 32, 1472–1507. DOI: 10.1039/C4NP00162A.
  • Calcio Gaudino, E.; Tagliapietra, S.; Martina, K.; Palmisano, G.; Cravotto, G. Recent Advances and Perspectives in the Synthesis of Bioactive Coumarins. RSC Adv. 2016, 6, 46394–46405. DOI: 10.1039/C6RA07071J.
  • Patra, P. A Concise Review on Pyridocoumarin/Azacoumarin Derivatives: Synthesis and Biological Activity. ChemistrySelect 2019, 4, 2024–2043. DOI: 10.1002/slct.201803596.
  • Majumdar, K. C.; Ansary, I.; Samanta, S.; Roy, B. Regioselective Synthesis of Pyridoquinolones and Pyridocoumarins via Molecular Iodine-Mediated 6-Endo-Dig Electrophilic Cyclization. Tetrahedron Lett. 2011, 52, 411–414. DOI: 10.1016/j.tetlet.2010.11.066.
  • Symeonidis, T. S.; Kallitsakis, M. G.; Litinas, K. E. Synthesis of [5,6]-Fused Pyridocoumarins through Aza-Claisen Rearrangement of 6-Propargylamino-Coumarins. Tetrahedron Lett. 2011, 52, 5452–5455. DOI: 10.1016/j.tetlet.2011.08.012.
  • Ahn, S.; Yoon, J. A.; Han, Y. T. Total Synthesis of the Natural Pyridocoumarins Goniothaline A and B. Synthesis 2019, 51, 552–556. DOI: 10.1055/s-0037-1610909.
  • Symeonidis, T. S.; K. E. Litinas, K. E. Synthesis of Methyl Substituted [5,6]- and [7,8]-Fused Pyridocoumarins via the Iodine-Catalyzed Reaction of Aminocoumarins with n-Butyl Vinyl Ether. Tetrahedron Lett. 2013, 54, 6517–6519. DOI: 10.1016/j.tetlet.2013.09.089.
  • Galariniotou, E.; Fragos, V.; Makri, A.; Litinas, K. E.; Nicolaides, D. N. Synthesis of Novel Pyridocoumarins and Benzo-Fused 6-Azacoumarins. Tetrahedron 2007, 63, 8298–8304. DOI: 10.1016/j.tet.2007.05.102.
  • Lipeeva, A. V.; Khvostov, M. V.; Baev, D. S.; Shakirov, M. M.; Tolstikova, T. G.; Shults, E. E. Synthesis, in Vivo Anticoagulant Evaluation and Molecular Docking Studies of New Groups of Bicoumarins Obtained from Furocoumarin Peucedanin. Med. Chem. 2016, 12, 674–683. DOI: 10.2174/1573406412666160129105115.
  • Mukusheva, G. K.; Lipeeva, A. V.; Zhanymkhanova, P. Z.; Shults, E. E.; Gatilov, Y. V.; Shakirov, M. M.; Adekenov, S. M. The Flavanone Pinostrobin in the Synthesis of Coumarin-Chalcone Hybrids with a Triazole Linker. Chem. Heterocycl. Comp. 2015, 51, 146–152. DOI: 10.1007/s10593-015-1672-y.
  • Lipeeva, А. V.; Shults, E. E. A Study of Plant Coumarins 16. Synthesis and Transformations of 7-Alkynylcoumarins. Chem. Heterocycl. Comp. 2017, 53, 1302–1309. DOI: 10.1007/s10593-018-2210-5.
  • Lipeeva, A. V.; Brysgalov, A. O.; Tolstikova, T. G.; Shults, E. E. Synthesis, Transformations and Characterization of 8 Aminomethyl Substituted Umbelliferones as Probable Anti-Arrhythmic Agents. Cbc. 2019, 15, 71–82. DOI: 10.2174/1573407213666171030152601.
  • For rev., see: (a) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry. A Guide for the Synthetic Chemist. Tetrahedron Organic Chemistry Series; Pergamon: Amsterdam, 2002; Vol. 20, pp 413–448. DOI: 10.1021/cr020085h. (b) Zeni, G.; Larock, R. C. Synthesis of Heterocycles via Palladium π-Olefin and π-Alkyne Chemistry. Chem. Rev. 2004, 104, 2285–2309. (c) Godoi, B.; Schumacher, R. F.; Zeni, G. Synthesis of Heterocycles via Electrophilic Cyclization of Alkynes Containing Heteroatom. Chem. Rev. 2011, 111, 2937–2980. DOI: 10.1021/cr100214d. (d) Wu, X.-F.; Neumann, H.; Beller, M. Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations. Chem. Rev. 2013, 113, 1–35. DOI: 10.1021/cr300100s. (e) Yamamoto, Y. Synthesis of Heterocycles via Transition-Metalcatalyzed Hydroarylation of Alkynes. Chem Soc Rev 2014, 43, 1575–1600. DOI: 10.1039/c3cs60369e.
  • Sharma, N.; Asthana, M.; Nandini, D.; Singh, R. P.; Singh, R. M. An Economical Nucleophilic Route toward Facile Synthesis of Pyrano[4,3-b]Quinolin-1-Ones via 6-Endo-Dig Cyclization of o-Alkynylquinoline Esters. Tetrahedron 2013, 69, 1822–1829. DOI: 10.1016/j.tet.2012.12.068.
  • Kumar, R.; Asthana, M.; Singh, R. M. Pd-Catalyzed One-Pot Stepwise Synthesis of Benzo[b][1,6]Naphthyridines from 2-Chloroquinoline-3-Carbonitriles Using Sulfur and Amines as Nucleophiles. J. Org. Chem. 2017, 82, 11531–11542. DOI: 10.1021/acs.joc.7b02147.
  • Wu, M.-J.; Chang, L.-J.; Wei, L.-M.; Lin, C.-F. A Direct Anionic Cyclization of 2-Alkynylbenzonitrile to 3-Substituted-1(2H)-Isoquinolones and 3-Benzylideneisoindol-20 Ones Initiated by Methoxide Addition. Tetrahedron 1999, 55, 13193–13200. DOI: 10.1016/S0040-4020(99)00812-1.
  • Wei, L. M.; Lin, C. F.; Wu, M. J. Palladium-Catalyzed Coupling of Aryl Iodides with 2-Alkynylbenzonitriles. Tetrahedron Lett. 2000, 41, 1215–1218. DOI: 10.1016/S0040-4039(99)02254-6.
  • Li, J.; Chen, L.; Chin, E.; Lui, A. S.; Zecic, H. Platinum(II)-Catalyzed Intramolecular Cyclization of Alkynylbenzonitriles: Synthesis of 1-Alkoxyisoquinolines and Isoquinolones. Tetrahedron Lett. 2010, 51, 6422–6425. DOI: 10.1016/j.tetlet.2010.09.136.
  • Reddy, V.; Jadhav, A. S.; Anand, R. V. Catalyst‐Controlled Regioselective Approach to 1‐Aminoisoquinolines and/or 1‐Aminoisoindolines through Aminative Domino Cyclization of 2‐Alkynylbenzonitriles. Eur. J. Org. Chem. 2016, 2016, 453–458. DOI: 10.1002/ejoc.201501390.
  • Liu, X.; Deng, G.; Liang, Y. Selective Synthesis of Benzo[4,5]Imidazo[2,1-a]Isoquinolines via Copper-Catalyzed Tandem Annulation of Alkynylbenzonitriles with 2-Iodoanilines. Tetrahedron Lett. 2018, 59, 2844–2847. DOI: 10.1016/j.tetlet.2018.06.030.
  • Ye, P.; Shao, Y.; Xie, L.; Shen, K.; Cheng, T.; Chen, J. Lanthanide-Catalyzed Tandem Insertion of Secondary Amines with 2-Alkynylbenzonitriles: Synthesis of Aminoisoindoles. Chem. Asian J. 2018, 13, 3681–3690. DOI: 10.1002/asia.201801252.
  • Lipeeva, A. V.; Baev, D. S.; Dolgikh, M. P.; Tolstikova, T. G.; Shults, E. E. Access to Oxazine Fused Furocoumarins and in Vivo and in Silico Studies of Theirs Biological Activity. Med. Chem. 2017, 13, 625–632. DOI: 10.2174/1573406413666170601114527.
  • Lipeeva, A. V.; Zakharov, D. O.; Burova, L. G.; Frolova, T. S.; Baev, D. S.; Shirokikh, I. V.; Evstropov, A. N.; Sinitsyna, O. I.; Tolsikova, T. G.; Shults, E. E. Design, Synthesis and Antibacterial Activity of Coumarin-1,2,3-Triazole Hybrids Obtained from Natural Furocoumarin Peycedanin. Molecules 2019, 24, 2126. DOI: 10.3390/molecules24112126.
  • Shults, E. E.; Petrova, T. N.; Shakirov, M. M.; Chernyak, E. I.; Pokrovskii, L. M.; Nekhoroshev, S. A.; Tolstikov, G. A. Coumarins from the Roots of Peucedanum morisonii Bess. Chem. Sust. Dev. 2003, 11, 649–654.
  • Bagryanskaya, I. Y.; Gatilov, Y. V.; Osadchii, S. A.; Martynov, A. A.; Shakirov, M. M.; Shul'ts, E. E.; Tolstikov, G. A. Plant Coumarins. 2. Beckman Rearrangement of Oreoselone E- and Z-Oximes. Chem. Nat. Compd. 2005, 41, 657–662. DOI: 10.1007/s10600-006-0006-9.
  • He, Y.; Zhang, X.; Fan, X. Synthesis of Naphthalene Amino Esters and Arylnaphthalene Lactone Lignans through Tandem Reactions of 2-Alkynylbenzonitriles. Chem. Commun. 2014, 50, 5641–5643. DOI: 10.1039/C4CC01738B.
  • Asagarasu, A.; Matsui, T.; Hayashi, H.; Tamaoki, S.; Yamauchi, Y.; Sato, M. Design and Synthesis of Piperazinylpyridine Derivatives as Novel 5-HT1A Agonists/5-HT3 Antagonists for the Treatment of Irritable Bowel Syndrome (IBS). Chem. Pharm. Bull. 2009, 57, 34–42. DOI: 10.1248/cpb.57.34.
  • Kobayashi, K.; Shiokawa, T.; Morikawa, O.; Konishi, H. New Synthesis of Isoquinoline Derivatives by Reactions of 2-(2-Methoxyethenyl)Benzonitriles with Organolithiums and Lithium Dialkylamides. Chem. Lett. 2004, 33, 236–237. DOI: 10.1246/cl.2004.236.
  • Rouchet, J.-B. E. Y.; Schneider, C.; Fruit, C.; Hoarau, C. Regioselective Decarboxylative Cross-Coupling of Carboxy Isoquinoline N-Oxides. J. Org. Chem. 2015, 80, 5919–5927. DOI: 10.1021/acs.joc.5b00475.
  • Si, C.; Myers, A. G. Versatile Synthesis of Substituted Isoquinolines. Angew. Chem. Int. Ed. 2011, 50, 10409–10413. DOI: 10.1002/anie.201104769.
  • Wang, T.; Li, R.; Yu, D.; Gu, C.; Xiong, F.; Chen, Z. Paper Synthesis of 1-Aminoisoquinolines via the Coinage Metal Cocatalyzed Reaction of 2-Alkynylbenzaldoximes with Isocyanoacetates. Synthesis 2014, 46, 3213–3220. DOI: 10.1055/s-0034-1378654;.
  • Li, Y.; Gao, L.; Zhu, H.; Li, G.; Chen, Z. Silver Triflate and Triflic Anhydride-Promoted Expedient Synthesis of Acylated 1-Aminoisoquinolines. Org. Biomol. Chem. 2014, 12, 6982–6985. DOI: 10.1039/C4OB01301H.
  • Kaishap, P. P.; Duarah, G.; Chetia, D.; Gogoi, S. Ru(II)-Catalyzed Annulation of Benzamidines and Alkynes by C–H/N–H Activation: A Facile Synthesis of 1-Aminoisoquinolines. Org. Biomol. Chem. 2017, 15, 3491–3498. DOI: 10.1039/C7OB00389G.
  • Yao, T.; Liang, X.; Guo, Z.; Yang, D. Highly Stereoselective Synthesis of (Z)-3-Methoxy-1-Methyleneisoindoles via DMAP Catalyzed Cyclization of Methyl 2-Alkynylbenzimidates. Tetrahedron 2019, 75, 3088–3100. DOI: 10.1016/j.tet.2019.04.036.
  • Dheer, D.; Singh, V.; Shankar, R. Medicinal Attributes of 1,2,3-Triazoles: Current Developments. Bioorg. Chem. 2017, 71, 30–54. DOI: 10.1016/j.bioorg.2017.01.010.
  • Fan, Y.-L.; Ke, X.; Liu, M. Coumarin–Triazole Hybrids and Their Biological Activities. J. Heterocyclic Chem. 2018, 55, 791–802. DOI: 10.1002/jhet.
  • Lorenzer, C.; Streußnig, S.; Tot, E.; Winkler, A.-M.; Merten, H.; Brandl, F.; Sayers, E. J.; Watson, P.; Jones, A. T.; Zangemeister-Wittke, U.; et al. Targeted Delivery and Endosomal Cellular Uptake of DARPin-siRNA Bioconjugates: Influence of Linker Stability on Gene Silencing. Eur. J. Med. Chem. 2019, 141, 37–50. DOI: 10.1016/j.ejpb.2019.05.015.
  • Pola, R.; Braunová, A. R.; Laga, R.; Pechar, M.; Ulbrich, K. Click Chemistry as a Powerful and Chemoselective Tool for the Attachment of Targeting Ligands to Polymer Drug Carriers. Polym. Chem. 2014, 5, 1340–1350. DOI: 10.1039/C3PY01376F.
  • Roberts, D. A.; Schmidt, T. W.; Crossley, M. J.; Perrier, S. Tunable Self-Assembly of Triazole-Linked Porphyrin–Polymer Conjugates. Chem. Eur. J. 2013, 19, 12759–12770. DOI: 10.1002/chem.201301133.
  • Kakuta, T.; Yamagishi, T.; Ogoshi, T. Supramolecular Chemistry of Pillar[n]Arenes Functionalised by a Copper(I)-Catalysed Alkyne–Azide Cycloaddition ‘‘Click’’ Reaction. Chem. Commun. 2017, 53, 5250–5266. DOI: 10.1039/C7CC01833A.
  • Mohamed, Z. H.; El-Koussi, N. A.; Mahfouz, N. M.; Youssef, A. F.; Jaleel, G. A. A.; Shouman, S. A. Cu (I) catalyzed Alkyne-Azide 1,3-Dipolar Cycloaddition (CuAAC): Synthesis of 17a-[1-(Substituted Phenyl)-1,2,3-Triazol-4-yl]-19-Nortestosterone-17b-yl Acetates Targeting Progestational and Antiproliferative Activities. Eur. J. Med. Chem. 2015, 97, 75–82. DOI: 10.1016/j.ejmech.2015.04.045.
  • Makhniova, E. A.; Lipeeva, A. V.; Shul'ts, E. E. Study of Plant Coumarins: XIV. Catalytic Amination of 7-Hydroxycoumarins Derivatives. Russ. J. Org. Chem. 2014, 50, 662–669. DOI: 10.1134/S107042801405008X.
  • Liang, Y.; Tao, L.-M.; Zhang, Y.-H.; Li, J.-H. Palladium-Catalyzed Cross-Coupling Reactions of 1,2-Diiodoalkenes with Terminal Alkynes: Selective Synthesis of Unsymmetrical Buta-1,3-Diynes and 2-Ethynylbenzofurans. Synthesis 2008, 24, 3988–3994. DOI: 10.1055/s-0028-1083251.

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