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Research Article

Cobalt-catalyzed domino C-N cross-coupling reaction between phenyl(2-halo)isothiourea and aryl halide

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Pages 559-568 | Received 24 Sep 2020, Accepted 01 Jan 2021, Published online: 27 Jan 2021

References

  • (a) Zirngibl, L.; Antifungal Azoles A Comprehensive Survey of Their Structures and Properties; Wiley-VCH: Weinheim, 1998; p. 242. doi.org/10.1021/op990014t. (b) Aiello, S.; Wells, G.; Stone, E. L. Synthesis and Biological Properties of Benzothiazole, Benzoxazole, and Chromen-4-one Analogues of the Potent Antitumor Agent 2-(3,4-Dimethoxyphenyl)-5-fluorobenzothiazole. J. Med. Chem. 2008, 51, 5135–5139. DOI: 10.1021/jm800418z. (c) Noel, S.; Gras, S.; Hureau, E. The Benzazole Scaffold: A SWAT to Combat Alzheimer’s Disease. Chem. Soc. Rev. 2013, 42, 7747–7762. DOI: 10.1039/c3cs60086f. (d) Westwell, A. D.; Weekes, A. A.; Weekes, A. 2-Arylbenzothiazole as a Privileged Scaffold in Drug Discovery. Curr. Med. Chem. 2009, 16, 2430–2440. DOI: 10.2174/092986709788682137. (e) Shi, D. F.; Bradshaw, T. D.; Wrigley, S. P. Antitumor Benzothiazoles. Synthesis of 2-(4-Amino phenyl) benzo-thiazoles and Evaluation of Their Activities against Breast Cancer Cell Lines in Vitro and in Vivo. J. Med. Chem. 1996, 39, 3375–3384. DOI: 10.1021/jm9600959. (f) Stevens, M. F. G.; McCall, C. J.; Lelieveld, P. Synthesis of Polyhydroxylated 2-Phenylbenzothiazoles and a Comparison of their Cytotoxicities and Pharmacological Properties with Genistein and Quercetin. J. Med. Chem. 1994, 37, 1689. DOI: 10.1021/jm00037a020. (g) Young, R. C.; Mitchell, R. C.; Brown, T. Development of a New Physicochemical Model for Brain Penetration and Its Application to the Design of Centrally Acting H2 Receptor Histamine Antagonists. J. Med. Chem. 1988, 31, 656–671. DOI: 10.1021/jm00398a028. (h) Paget, C. J.; Kisner, K.; Stone, R. L. Heterocyclic Substituted Ureas. II. Immunosuppressive and Antiviral Activity of Benzothiazolyl- and Benzoxazolylureas. J. Med. Chem. 1969, 12, 1016–1018. DOI: 10.1021/jm00306a011. (i) Jordan, A. D.; Chi, L.; Reitz, A. B. Efficient Conversion of Substituted Aryl Thioureas to 2-Aminobenzothiazoles Using Benzyltrimethylammonium Tribromide. J. Org. Chem. 2003, 68, 8693–8696. DOI: 10.1021/jo0349431. (j) Armenise, D.; Laurentis, N. D.; Reho, A. Synthesis and Antifungal Activity Against Strains of Candida albicans of 6-Fluoro-4 (5 or 7)-chloro-2(difluorobenzoyl) Aminobenzothiazoles. J. Heterocycl. Chem. 2004, 41, 771–775.10.1002/jhet.5570410520. (k) Suter, H.; Zutter, H. Studien über Benzthiazole als eventuelle orale Antidiabetica. Helve. Chim. Acta. 1967, 50, 1084–1086.
  • (a) Alamgir, M.; Black, D. Synthesis, Reactivity and Biological Activity of Benzimidazoles. Topics Heterocycl. Chem. 2007, 9, 87–118. (b) Skalitzky, D. J.; Marakovits, J. T.; Maegley, K. A. Tricyclic Benzimidazoles as Potent Poly(ADP-ribose) Polymerase-1 Inhibitors. J. Med. Chem. 2003, 46, 210–213. 10.1021/jm0255769. (c) Valdez, J.; Cedillo, R.; Hernandez-Campos, A. Synthesis and Antiparasitic Activity of 1H-Benzimidazole Derivatives. Med. Chem. Lett. 2002, 12, 2221–2224. DOI: http://doi.org/10.1016/s0960-894x(02)00346-3. (e) Horton, D. A.; Bourne, G. T.; Smythe, M. L. The Combinatorial Synthesis of Bicyclic Privileged Structures or Privileged Substructures. Chem. Rev. 2003, 103, 893–930. DOI: 10.1021/cr020033s. (f) Yamamoto, Y.; Mizuno, H.; Tsuritani, T. CuI-Catalyzed Amination of Arylhalides with Guanidines or Amidines: A Facile Synthesis of 1-H-2-Substituted Benzimidazoles. J. Org. Chem. 2009, 74, 1394–1396. DOI: 10.1021/jo900912h. (g) Bahrami, K.; Khodaei, M. M.; Naali, F. Mild and Highly Efficient Method for the Synthesis of 2-Arylbenzimidazoles and 2-Arylbenzothiazoles. J. Org. Chem. 2008, 73, 6835–6837. DOI: 10.1021/jo8010232. (h) Shen, M.; Driver, T. G. Iron (II) Bromide-Catalyzed Synthesis of Benzimidazoles from Aryl Azides. Org. Lett. 2008, 10, 3367–3370. DOI: 10.1021/ol801227f. (i) El.coffinier, D.; Kaim, L.; Grimaud, L. New Benzotriazole and Benzimidazole Scaffolds from Ugi − Smiles Couplings of Isocyanides. Org. Lett., 2009, 11, 995–997. DOI: 10.1021/ol8029438. (j) Goossen, L. J.; Knauber, T. Concise Synthesis of Telmisartan via Decarboxylative Cross-Coupling. J. Org. Chem. 2008, 73, 8631–8634. DOI: 10.1021/jo801937h.
  • (a) Ellingboe, J. W.; Spinelli, W. Class III Antiarrhythmic Activity of Novel Substituted 4-[(methylsulfonyl)amino] Benzamides and Sulfonamides J. Med. Chem. 1992, 35, 705–716. 10.1021/jm00082a011. (b) Janssens, F.; Torremans, J.; Janssen, M. New Antihistaminic N-heterocyclic 4-Piperidinamines. 2. Synthesis and Antihistaminic Activity of 1-[(4-fluorophenyl)methyl]-N-(4-piperidinyl)-1H-benzimidazol-2-amines. J. Med. Chem. 1985, 28, 1934–1943. DOI: 10.1021/jm00150a029. (c) Ozden, S.; Atabey, D.; Yildiz, S. Synthesis, Potent Anti-Staphylococcal Activity and QSARs of Some Novel 2-Anilinobenzazoles. Eur. J. Med. Chem. 2008, 43, 1390–1402. DOI: 10.1016/j.ejmech.2007.10.009. (d) Zhang, G.; Ren, P.; Gray, N. S. Discovery of Pyrimidine Benzimidazoles as Src-Family Selective Lck Inhibitors. Part II. Bioorg. Med. Chem. 2008, 18, 5618–5621. DOI: 10.1016/j.bmcl.2009.09.123.
  • (a) Shao, B.; Huang, J.; Sun, Q. 4-(2-Pyridyl)piperazine-1-benzimidazoles as Potent TRPV1 Antagonists. Bioorg. Med. Chem. 2005, 15, 719–723. 10.1016/j.bmcl.2004.11.021. (b) Bonfiant, J. F.; Meyer, C.; Doublet, F. Selection of a Respiratory Syncytial Virus Fusion Inhibitor Clinical Candidate. 2. Discovery of a Morpholinopropylaminobenzimidazole Derivative (TMC353121) J. Med. Chem. 2008, 51, 875–896. DOI: 10.1021/jm701284j.
  • Wu, Y.-Q.; Hamilton, S. K.; Wilkinson, D. E.; Hamilton, G. S. Direct Synthesis of Guanidines Using Di(Imidazole-1-yl)Methanimine. J. Org. Chem. 2002, 67, 7553–7556. DOI: 10.1021/jo0202381.
  • Easmon, J.; Pürstinger, G.; Thies, K.-S.; Heinisch, G.; Hofmann, J. Synthesis, Structure-Activity Relationships, and Antitumor Studies of 2-Benzoxazolyl Hydrazones Derived from Alpha-(N)-acyl Heteroaromatics. J. Med. Chem. 2006, 49, 6343–6350. DOI: 10.1021/jm060232u.
  • Sun, L.-Q.; Chen, J.; Bruce, M.; Deskus, J. A.; Epperson, J. R.; Takaki, K.; Johnson, G.; Iben, L.; Mahle, C. D.; Ryan, E.; Xu, C. Synthesis and Structure-Activity Relationship of Novel Benzoxazole Derivatives as Melatonin Receptor Agonists. Bioorg. Med. Chem. Lett. 2004, 14, 3799–3802. DOI: 10.1016/j.bmcl.2004.04.082.
  • Kumar, D.; Jacob, M. R.; Reynolds, M. B.; Kerwin, S. M. Synthesis and Evaluation of Anticancer Benzoxazoles and Benzimidazoles Related to UK-1. Bioorg. Med. Chem. 2002, 10, 3997–4004. DOI: 10.1016/s0968-0896. (02)00327-9. DOI: 10.1016/s0968-0896(02)00327-9.
  • McKee, M. L.; Kerwin, S. M. Synthesis, Metal Ion Binding, and Biological Evaluation of New Anticancer 2-(2'-Hydroxyphenyl)benzoxazole Analogs of UK-1. Bioorg. Med. Chem. 2008, 16, 1775–1783. DOI: 10.1016/j.bmc.2007.11.019.
  • Potashman, M. H.; Bready, J.; Coxon, A.; DeMelfi, T. M.; DiPietro, L.; Doerr, N.; Elbaum, D.; Estrada, J.; Gallant, P.; Germain, J.; et al., Synthesis, and Evaluation of Orally Active Benzimidazoles and Benzoxazoles as Vascular Endothelial Growth Factor-2 Receptor Tyrosine Kinase Inhibitors. J. Med. Chem. 2007, 50, 4351–4373. DOI: 10.1021/jm070034i.
  • Huang, S. T.; Hsei, I. J.; Chen, C. Synthesis, and Anticancer Evaluation of Bis(Benzimidazoles), Bis(Benzoxazoles), and Benzothiazoles. J. Med. Chem. 2006, 14, 6106–6119. 10.1016/j.bmc.2006.05.007.
  • Serdons, K.; Terwinghe, C.; Vermaelen, P.; Van Laere, K.; Kung, H.; Mortelmans, L.; Bormans, G.; Verbruggen, A. Synthesis and Evaluation of 18F-Labeled 2-Phenylbenzothiazoles as Positron Emission Tomography Imaging Agents for Amyloid Plaques in Alzheimer’s Disease. J. Med. Chem. 2009, 52, 1428–1437. DOI: 10.1021/jm8013376.
  • Praveen, C.; Nandakumar, A.; Dheenkumar, P.; Muralidharan, D.; Perumal, P. T. Microwave-Assisted One-Pot Synthesis of Benzothiazole and Benzoxazole Libraries as Analgesic Agents. J. Chem. Sci. 2012, 124, 609–624. DOI: https://www.ias.ac.in/article/fulltext/jcsc/124/03/0609-0624. DOI: 10.1007/s12039-012-0251-3.
  • Su, X.; Vicker, N.; Ganeshapillai, D.; Smith, A.; Purohit, A.; Reed, M. J.; Potter, B. V. L. Benzothiazole Derivatives as Novel Inhibitors of Human 11beta-hydroxysteroid Dehydrogenase Type 1. Mol. Cell. Endocrinol. 2006, 248, 214–217. DOI: 10.1016/j.mce. 2005.10.022. DOI: 10.1016/j.mce.2005.10.022.
  • Yalcin, I.; Oren, I.; Sener, E. The Synthesis and the Structure-Activity Relationships of Some Substituted Benzoxazoles, Oxazolo(4,5-b) Pyridines, Benzothiazoles and Benzimidazoles as Antimicrobial Agents. Eur. J. Med. Chem. 1992, 27, 401–406. 10.1016/0223-5234(92)90154-S.
  • (a) Sun, Q.; Wu, R. Z.; Cai, S. T. Synthesis and Biological Evaluation of Analogues of AKT (Protein Kinase B) Inhibitor-IV. J. Med. Chem. 2011, 54, 1126–1139. 10.1021/jm100912b. (b) Bradshaw, T. D.; Westwell, A. D. The Development of the Antitumour Benzothiazole Prodrug, Phortress, as a Clinical Candidate. Curr. Med. Chem. 2004, 11, 1241. DOI: 10.2174/0929867043455530. (c) Huang, S. T.; Hsei, I. J.; Chenm, C. P. Synthesis and Anticancer Evaluation of Bis(benzimidazoles), Bis(benzoxazoles), and Benzothiazoles. Bioorg. Med. Chem. 2006, 14, 6106–6119. DOI: 10.1016/j.bmc.2006.05.007. (d) Bergman, J. M.; Coleman, P. J.; Cox, C. Organic Phosphorus Compounds. 1. 4-(Benzothiazol-2-yl) benzylphosphonate as Potent Calcium Antagonistic Vasodilator. J. Med. Chem. 1986, 29, 820–825. DOI: 10.1021/jm00155a037. (e) Mylari, B. L.; Larson, E. R.; Beyer, W. J. Novel, potent Aldose Reductase Inhibitors: 3,4-Dihydro-4-oxo-3-[[5-(trifluoromethyl)-2-benzothiazolyl]methyl]-1-phthalazineacetic Acid (zopolrestat) and Congeners. J. Med. Chem. 1991, 34, 108–122. DOI: 10.1021/jm00105a018.
  • (a) Tale, R. H. Novel Synthesis of 2-Arylbenzothiazoles Mediated by Ceric Ammonium Nitrate (CAN). Org. Lett. 2002, 4, 1641–1642. 10.1021/ol020027i. (b) Alagille, D.; Baldwin, R. M.; Tamagnan, G. D. One-Step Synthesis of 2-Arylbenzothiazole (‘BTA’) and -Benzoxazole Precursors for In Vivo Imaging of β-Amyloid Plaques. Tetrahedron Lett. 2005, 46, 1349–1351. DOI: 10.1016/j.tetlet.2004.12.111. (c) Itoh, T.; Mase, T. A. A Novel Practical Synthesis of Benzothiazoles via Pd-Catalyzed Thiol Cross-Coupling. Org. Lett. 2007, 9, 3687–3689. DOI: 10.1021/ol7015737. (d) Evindar, G.; Batey, R. A. Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides. J. Org. Chem. 2006, 71, 1802–1808. DOI: 10.1021/jo051927q. (e) Jaseer, E. A.; Prasad, D. J. C.; Dandapat, A. An Efficient Copper (II)-Catalyzed Synthesis of Benzothiazoles through Intramolecular Coupling-Cyclization of N-(2-chlorophenyl) Benzothioamides. Tetrahedron Lett. 2010, 51, 5009–5012. DOI: 10.1016/j.tetlet.2010.07.079. (f) Yu, H.; Zhang, M.; Li, Y. Copper-Catalyzed Synthesis of Benzo[b]thiophenes and Benzothiazoles Using Thiocarboxylic Acids as a Coupling Partner. J. Org. Chem. 2013, 78, 8898–8903. DOI: 10.1021/jo401353w. (g) Zhang, X.; Zeng, W.; Yang, Y. Copper-Catalyzed Double C–S Bonds Formation via Different Paths: Synthesis of Benzothiazoles from N- Benzyl-2-iodoaniline and Potassium Sulfide. Org. Lett. 2014, 16, 876–879. DOI: 10.1021/ol403638d. (h) Deng, H.; Li, Z.; Ke, F. Cu-Catalyzed Three-Component Synthesis of Substituted Benzothiazoles in Water. Chem.–Eur. J. 2012, 18, 4840–4843. DOI: 10.1002/chem.201103525. (i) Ma, D.; Xie, S.; Xue, P. Efficient and Economical Access to Substituted Benzothiazoles: Copper-Catalyzed Coupling of 2-Haloanilides with Metal Sulfides and Subsequent Condensation. Chem. Int. Ed. 2009, 48, 4222–4225. DOI: 10.1002/anie.200900486. (j) Fernandez Rodrıguez, M. A.; Shen, Q.; Hartwig, J. F.; General and Long-Lived Catalyst for the Palladium-Catalyzed Coupling of Aryl Halides with Thiols. J. Am. Chem. Soc. 2006, 128, 2180–2181. DOI: 10.1021/ja0580340. (k) Lv, X.; Bao, W. A. β-Keto Ester as a Novel, Efficient, and Versatile Ligand for Copper (I)-Catalyzed C-N, C-O, and C-S Coupling Reactions. J. Org. Chem. 2007, 72, 3863–3867. DOI: 10.1021/jo070443m. (m) Rout, L.; Sen, T. K.; Punniyamurthy, T. Efficient CuO‐Nanoparticle‐Catalyzed C-S Cross‐Coupling of Thiols with Iodobenzene. Chem. Int. Ed. 2007, 46, 5583–5586. DOI: 10.1002/anie.200701282. (n) Saha, P.; Ramana, T.; Purkait, N. Ligand-Free Copper-Catalyzed Synthesis of Substituted Benzimidazoles, 2-Aminobenzimidazoles, 2-Aminobenzothiazoles, and Benzoxazoles. J. Org. Chem. 2009, 74, 8719–8725. DOI: 10.1021/jo901813g. (o) Joyce, L. L.; Evindar, G.; Batey, R. A. Copper- and Palladium-Catalyzed Intramolecular C–S Bond Formation: A Convenient Synthesis of 2-Aminobenzothiazoles. Chem. Commun. 2004, 446–447. DOI: 10.1039/b311591g. (p) Ding, Q.; He, X.; Wu, J. Synthesis of 2-Aminobenzothiazole via Copper (I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate. J. Comb. Chem. 2009, 11, 587–591. DOI: 10.1021/cc900027c. (q) Shen, G.; Lv, X.; Bao, W. Synthesis of N-Substituted-2-Aminobenzothiazoles by Ligand-Free Copper(I)-Catalyzed Cross-Coupling Reaction of 2-Haloanilines with Isothiocyanates. Eur. J. Org. Chem. 2009, 5897–5901. DOI: 10.1002/ejoc.200900953.
  • (a) Guo, Y. J.; Tang, R. Y.; Zhong, P. Copper-Catalyzed Tandem Reactions of 2-Halobenzenamines with Isothiocyanates Under Ligand- and Base-Free Conditions. Tetrahedron Lett. 2010, 51, 649–652. DOI: 10.1016/j.tetlet.2009.11.086. (b) Ramana, T.; Saha, P. M.; Das, T. Copper-Catalyzed Domino Intra- and Intermolecular C-S Cross-Coupling Reactions: Synthesis of 2-(Arylthio)arylcyanamides. Org. Lett. 2010, 12, 84–87. DOI: 10.1021/ol9024088. (c) Sahoo, S. K.; Jamir, L.; Guin, S. Copper (I)-Catalyzed Cascade Synthesis of 2-Aryl sulfanylarylcyanamides. Adv. Synth. Catal. 2010, 352, 2538–2548. DOI: 10.1002/adsc.201000383. (d) Itoh, T.; Mase, T. A. Novel Practical Synthesis of Benzothiazoles via Pd-Catalyzed Thiol Cross-Coupling. Org. Lett. 2007, 9, 3687–3689. DOI: 10.1021/ol7015737. (e) Cheng, Y.; Peng, Q.; Fan, W. J. Org. Chem. 2014, 79, 5812–5819. DOI: 10.1021/jo5002752. (f) Inamoto, K.; Hasegawa, C.; Hiroya, K. Room-Temperature Ligand-Free Pd/C-Catalyzed C–S Bond Formation: Synthesis of 2-Substituted Benzothiazoles. Org. Lett. 2008, 10, 5147–5150. DOI: 10.1021/ol802033p. (g) Inamoto, K.; Hasegawa, C.; Kawasaki, J. Palladium-Catalyzed Synthesis of 2-Substituted Benzothiazoles via a C − H Functionalization/Intramolecular C − S Bond Formation Process. Adv. Synth. Catal. 2010, 352, 2643–2655. DOI: 10.1002/adsc. 201000604. DOI: 10.1016/j.tetlet.2009.11.086.
  • (a) Migita, T.; Shimizu, T.; Asami, Y. Bull. Chem. Soc. 1980, 53, 1385–1389. (b) Li, G. Y.; Zheng, G.; Noonan, A. F. Highly Active, Air-Stable Versatile Palladium Catalysts for the C − C, C − N, and C − S Bond Formations via Cross-Coupling Reactions of Aryl Chlorides. J. Org. Chem. 2001, 66, 8677–8681. 10.1021/jo010764c.
  • (a) Joyce, L. L.; Batey, R. A. Heterocycle Formation via Palladium-Catalyzed intra molecular Oxidative C − H Bond Functionalization: An Efficient Strategy for the Synthesis of 2-Aminobenzothiazoles. Org. Lett. 2009, 11, 2792–2795. 10.1021/ol900958z. (b) Cheng, Y.; Yang, J.; Qu, Y. Aerobic Visible-Light Photoredox Radical C–H Functionalization: Catalytic Synthesis of 2-Substituted Benzothiazoles. Org. Lett. 2012, 14, 98–101. DOI: 10.1021/ol2028866. (c) Zhang, G.; Liu, C.; Yi, H. External Oxidant-Free Oxidative Cross-Coupling: A Photoredox Cobalt-Catalyzed Aromatic C–H Thiolation for Constructing C–S Bonds. J. Am. Chem. Soc. 2015, 137, 9273–9280. DOI: 10.1016/j.bmcl.2008.08.104. (d) Qiu, J. W.; Zhang, X. G.; Tang, R. Y. Iron-Catalyzed Tandem Reactions of 2-Halobenzenamines with Isothiocyanates Leading to 2-Aminobenzothiazoles. Adv. Synth. Catal. 2009, 351, 2319–2323. DOI: 10.1002/adsc. 200900450.
  • Murthy, B. S. N.; Kurmarayuni, C. M.; Mutchu, B. M.; Tamminana, R.; Bollikolla, H. B. Copper-Catalyzed Synthesis of 2-Aminophenyl Benzothiazoles: A Novel Approach. Org. Biomol. Chem. 2018, 16, 8267–8272. 10.1039/C8OB02018C.
  • (a) Ding, Q.; He, X.; Wu, J. New Convenient Four-Component Synthesis of 6-Amino-2,4-dihydropyrano[2,3-c]pyrazol-5-carbonitriles and One-Pot Synthesis of 6′-Aminospiro[(3H)-indol-3,4′- pyrano[2,3-c] pyrazol]-(1H)-2-on-5′-carbonitriles. J. Comb. Chem. 2009, 11, 587. DOI: 10.1021/cc900076j..(b) Miloudi, A.; El-Abed, D.; Boyer, G.; Finet, J. P.; Galy, J. P.; Siri, D. Utilisation of 1,3‐Dicarbonyl Derivatives in Multicomponent Reactions. Eur. J. Org. Chem. 2004, 1509–1516. DOI: 10.1002/ejoc.200400511. (c) Evindar, G.; Batey, R. A. Parallel Synthesis of a Library of Benzoxazoles and Benzothiazoles Using Ligand-Accelerated Copper-Catalyzed Cyclizations of ortho-Halobenzanilides. J. Org. Chem. 2006, 71, 1802. DOI: 10.1021/jo051927q.
  • Ding, Q.; Cao, B.; Liu, X.; Zong, Z.; Peng, Y.-Y. Synthesis of 2-Aminobenzothiazole via FeCl3-Catalyzed Tandem Reaction of 2 Iodoaniline with Isothiocyanate in Water. Green Chem. 2010, 12, 1607–1610. DOI: 10.1039/c0gc00123f.
  • (a) Wang, H.; Wang, L.; Shang, J. Fe-Catalysed Oxidative C–H Functionalization/C–S Bond Formation. Chem. Commun. 2012, 48, 76–78. 10.1039/c1cc16184a. (b) Ramana, T.; Punniyamurthy, T. Preparation of 2-Azido-1-Substituted-1H-Benzo[d]imidazoles Using a Copper-Promoted Three-Component Reaction and Their Further Conversion into 2-Amino and 2-Triazolyl Derivatives. Chem. Eur. J. 2012, 18, 13279–13283. DOI: 10.1002/chem.201202215. (c) Usharani, M.; Srinivasarao, P.; Rameshraju, R. Copper Promoted Desulfurization Towards the Synthesis of Isothiocyanates. Tetrahedron Lett. 2017, 58, 125–128. DOI: 10.1016/j.tetlet.2016.11.086. (d) Batey, R. A.; Powell, D. A. A General Synthetic Method for the Formation of Substituted 5-Aminotetrazoles from Thioureas: A Strategy for Diversity Amplification. Org. Lett. 2000, 2, 3237–3240. DOI: 10.1021/ol006465b.
  • (a) Mohan, S.; Bajavali, S.; Ramana, T. An Efficient Methodology for the Synthesis of Thioureas from Amine Mediated by a Cobalt Source. Tetrahedron Lett. 2016, 57, 5297–5300. 10.1016/j.tetlet.2016.09.092. (b) Mohan, S.; Bajavali, S. K.; Prasadrao, K. Cobalt Mediated by Desulfurization Toward the Synthesis of Isothiocyanates. Synth Comm. 2016, 46, 1759–1765. DOI: 10.1080/00397911.2016.1224351. (c) Ali, A. R.; Ghosh, H.; Patel, B. K. A Greener Synthetic Protocol for the Preparation of Carbodiimide. Tetrahedron Lett. 2010, 51, 1019–1021. DOI: 10.1016/j.tetlet.2009.12.017. (d) Guin, S.; Rout, S. K.; Gogoi, A. Desulfurization Strategy in the Construction of Azoles Possessing Additional Nitrogen, Oxygen or Sulfur using a Copper (I) Catalyst. Adv. Synth. Catal. 2012, 354, 2757–2770. DOI: 10.1002/adsc.201200408. (e) Yella, R.; Khatun, N.; Rout, S. K. Tandem Regioselective Synthesis of Tetrazoles and Related Heterocycles Using Iodine. Org. Biomol. Chem. 2011, 9, 3235–3245. DOI: 10.1039/C0OB01007C. (f) Ghosh, H.; Yella, R.; Nath, J. Desulfurization Mediated by Hypervalent Iodine (III): A Novel Strategy for the Construction of Heterocycle. Eur. J. Org. Chem. 2008, 6189–6196. DOI: 10.1002/ejoc.200800901. (g) Nath, J.; Ghosh, H.; Yella, R. Molecular Iodine Mediated Preparation of Isothiocyanates from Dithiocarbamic Acid Salts. Eur. J. Org. Chem. 2009, 1849–1851. DOI: 10.1002/ejoc.200801270. (i) Guin, S.; Rout, S. K.; Khatun, N.; Ghosh, T.; Patel, B. K. Tandem Synthesis of [1,2,4]-Triazoles Mediated by Iodine—A Regioselective Approach. Tetrahedron. 2012, 68, 5066–5074. DOI: 10.1016/j.tet.2012.04.042. (j) Sahoo, S. K.; Jamir, L.; Guin, S. Copper (I)‐Catalyzed Cascade Synthesis of 2‐Arylsulfanyl‐Arylcyanamides. Adv. Synth. Catal. 2010, 352, 2538–2548. DOI: 10.1002/adsc.201000383. (k) Ghosh, H.; Ramesh, Y.; Ali, A. R. An Efficient Synthesis of Cyanamide from Amine Promoted by a Hypervalent Iodine (III) Reagent. Tetrahedron Lett. 2009, 50, 2407–2410. DOI: 10.1016/j.tetlet.2009.03.017. (l) Nath, J.; Patel, B. K.; Jamir, L. A One-Pot Preparation of Cyanamide from Dithiocarbamate Using Molecular Iodine. Green Chem. 2009, 11, 1503–1506. DOI: 10.1039/B914283P. (m) Ding, Q.; He, X.; Wu, J. Synthesis of 2-Aminobenzothiazole via Copper(I)-Catalyzed Tandem Reaction of 2-Iodobenzenamine with Isothiocyanate. J. Comb. Chem. 2009, 11, 587–591. DOI: 10.1021/cc900027c.
  • (a) Wang, J.; Peng, F.; Jiang, J.; Lu, Z.; Wang, L.; Bai, J.; Pan, Y. Synthesis of N-benzothiazol-2-yl-amides by a Copper-Catalyzed Intramolecular Cyclization Process. Tetrahedron Lett. 2008, 49, 467–470. 10.1016/j.tetlet.2007.11.100. (b) Ramana, T.; Saha, P.; Das, M. Copper-Catalyzed Domino Intra- and Intermolecular C-S Cross-Coupling Reactions: Synthesis of 2-(Arylthio)arylcyanamides. Org. Lett. 2010, 12, 84–87. DOI: 10.1021/ol9024088. (c) Zhao, D.; Hu, J.; Wu, N. Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission. Org. Lett. 2011, 13, 6516–6519. DOI: 10.1021/ol202807d. (d) Lv, X.; Bao, W. Copper-Catalyzed Cascade Addition/Cyclization: An Efficient and Versatile Synthesis of N-substituted 2-heterobenzimidazoles. J. Org. Chem. 2009, 74, 5618–5621. DOI: 10.1021/jo900743y. (e) Saha, P.; Ali, M. A.; Ghosh, P. Cobalt-Catalyzed Intramolecular C–N and C–O Cross-Coupling Reactions: Synthesis of Benzimidazoles and Benzoxazoles. Org. Biomol. Chem. 2010, 8, 5692–5699. DOI: 10.1039/c0ob00405g. (f) Cahiez, G.; Moyeux, A. Cobalt-Catalyzed Cross-Coupling Reactions. Chem. Rev. 2010, 110, 1435–1462. DOI: 10.1021/cr9000786. (g) Tan, B. Y. H.; Teo, Y. O. Efficient Cobalt-Catalyzed C–N Cross-Coupling Reaction between Benzamide and Aryl Iodide in Water. Org. Biomol. Chem. 2014, 12, 7478–7481. DOI: 10.1039/C4OB01483A. (h) Amatore, M.; Gosmini, C. Cobalt-Catalyzed Cross-Coupling Reactions. Chem. Commun. 2008, 5019–5521. DOI: 10.1039/B805142A. (i) Hammann, J. M.; Haas, D.; Knochel, P. Cobalt-Catalyzed Negishi Cross-Coupling Reactions of (Hetero)Arylzinc Reagents with Primary and Secondary Alkyl Bromides and Iodides. Angew. Chem., Int. Ed. 2015, 54, 4478–4481. DOI: 10.1002/anie.201411960. (j) Zhao, D.; Hu, J.; Wu, N. X. Regiospecific Synthesis of 1,2-Disubstituted (Hetero)aryl Fused Imidazoles with Tunable Fluorescent Emission. Org. Lett. 2011, 13, 6516–6519. DOI: 10.1021/ol202807d. (k) Deng, X.; McAllister, H.; Mani, N. S. J. CuI-Catalyzed Amination of Arylhalides with Guanidines or Amidines: A Facile Synthesis of 1-H-2-Substituted Benzimidazoles. J. Org. Chem. 2009, 74, 5742–5745. DOI: 10.1021/jo900912h. (l) Lv, X.; Bao, W. J. Copper-Catalyzed Cascade Addition/Cyclization: An Efficient and Versatile Synthesis of N-Substituted 2-heterobenzimidazoles. J. Org. Chem. 2009, 74, 5618–5621. DOI: 10.1021/jo900743y.

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