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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 46, 2016 - Issue 4
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Original Articles

Convenient and efficient synthesis of 2-methyl-5-nitrobenzo[b]thiophene and its derivatives

Pages 332-337 | Received 22 Sep 2015, Published online: 21 Feb 2016

References

  • Majumdar, K. C; Mondal, S. In Heterocycles in Natural Product Synthesis; K. C. Majumdar, and S. K. Chattopadhyay (Eds.); Wiley-VCH Verlag, GmbH: Berlin, 2011; chapter 11, pp. 377–401.
  • (a) Qin, Z.; Kastrati, I.; Chandrasena, R. E. P.; Liu, H.; Yao, P.; Petukhov, P. A.; Bolton, J. L.; Thatcher, G. R. J. J. Med. Chem. 2007, 50, 2682–2692; (b) Hsiao C.-N.; Kolasa T. Tetrahedron Lett. 1992, 33, 2629–2632; (c) Vignon, J.; Pinet, V.; Cerruti, C.; Kamenka, J.-M.; Chicheportiche, R. Eur. J. Pharmacol. 1988, 148, 427–436.
  • (a) Tso, S.-C.; Gui, W.-J.; Wu, C.-Y.; Chuang, J. L.; Qi, X.; Skvorak, K. J.; Dorko, K.; Wallace, A. L.; Morlock, L. K.; Lee, B. H.; Hutson, S. M.; Strom, S. C.; Williams, N. S.; Tambar, U. K.; Wynn, R. M.; Chuang, D. T. J. Biol. Chem. 2014, 289, 20583–20593; (b) Wang, S.; Beck, R.; Blench, T.; Burd, A.; Buxton, S.; Malic, M.; Ayele, T.; Shaikh, S.; Chahwala, S.; Chander, C.; Holland, R.; Merette, S.; Zhao, L.; Blackney, M.; Watts, A. J. Med. Chem. 2010, 53, 1465–1472; (c) Villar, R.; Encio, I.; Migliaccio, M.; Gil, M. J.; Martinez-Merino, V. Bioorg. Med. Chem. 2004, 12, 963–968.
  • Irie, M.; Fukaminato, T.; Matsuda, K.; Kobatake, S. Chem. Rev. 2014, 114, 12174–12277.
  • Bertarelli, C.; Bianco, A.; Castagna, R.; Pariani, G. J. Photochem. Photobiol. C: Photochem. Rev. 2011, 12, 106–125.
  • Feringa, B. L. Molecular Switches; Wiley-VCH: Verlag, GmbH, 2001.
  • (a) Katritzky, A. R.; Serdyuk, L.; Xie, L. J. Chem. Soc., Perkin Trans. 1 1998, 1059–1064; (b) Capozzi, G.; Melloni, G.; Modena, G. J. Chem. Soc. C 1970, 2621–2625.
  • Takimiya, K.; Nakano, M.; Kang, M. J.; Miyazaki, E.; Osaka, I. Eur. J. Org. Chem. 2013, 217–227.
  • (a) Hsiao, C.-N.; Bhagavatula, L.; Pariza, R. J. Synth. Commun. 1990, 20, 1687–1695; (b) Gallagher, T.; Pardoe, D. A.; Porter, R. A. Tetrahedron Lett. 2000, 41, 5415–5418; (c) Gabriele, B.; Mancuso, R.; Lupinacci, E.; Veltri, L.; Salerno, G.; Carfagna, C. J. Org. Chem. 2011, 76, 8277–8286; (d) Wu, B.; Yoshikai, N. Angew. Chem. Int. Ed. 2013, 52, 10496–10499; (e) Watanabe, M.; Date, M.; Kawanishi, K.; Akiyoshi, R.; Furukawa, S. J. Heterocycl. Chem. 1991, 28, 173–176; (f) Roberts, C. F.; Hartley, R. C. J. Org. Chem. 2004, 69, 6145–6148.
  • Luyksaar, S. I.; Migulin, V. A.; Nabatov, B. V.; Krayushkin, M. M. Russ. Chem. Bull., Int. Ed. 2010, 59, 446–451.
  • (a) Krayushkin, M. M.; Migulin, V. A.; Yarovenko, V. N.; Barachevskii, V. A.; Vorontsova, L. G.; Starikova, Z. A.; Zavarzin, I. V.; Bulgakova, V. N. Mendeleev Commun. 2007, 17, 125–127; (b) Krayushkin, M. M.; Migulin, V. A. Patent, RU 2421453 (C1), June 20, 2011.
  • (a) Migulin, V. A.; Krayushkin, M. M.; Barachevskii, V. A.; Kobeleva, O. I.; Novikov, V. V.; Lyssenko, K. A. Tetrahedron 2015, 71, 584–598; (b) Migulin, V. A.; Krayushkin, M. M.; Barachevskii, V. A.; Kobeleva, O. I.; Valova, T. M.; Lyssenko, K. A. J. Org. Chem. 2012, 77, 332–340.
  • (a) Tatsumi, R.; Fujio, M.; Takanashi, S.-I.; Numata, A.; Katayama, J.; Satoh, H.; Shiigi, Y.; Maeda, J.-I.; Kuriyama, M.; Horikawa, T.; Murozono, T.; Hashimoto, K.; Tanaka, H. J. Med. Chem. 2006, 49, 4374–4383; (b) Cai, J.; Zhang, S.; Zheng, M.; Wu, X.; Chen, J.; Ji, M. Bioorg. Med. Chem. Lett. 2012, 22, 806–810; (c) Baraldi, P. G.; Beria, I.; Cozzi, P.; Bianchi, N.; Gambari, R.; Romagnoli, R. Bioorg. Med. Chem. 2003, 11, 965–975; (d) Abreu, A. S.; Silva, N. O.; Ferreira, P. M. T.; Queiroz, M.-J. R. P. Eur. J. Org. Chem. 2003, 1537–1544; (e) Gubin, G.; Chatelain, P.; Lucchetti, J.; Rosseels, G.; Inion, H. US Patent 5223510 (A), June 29, 1993; (f) Fritz, J. E..; Kaldor, S. W..; Liang, S. X..; Singh, U.; Xu, Y.-C. US Patent 5792763 (A), Aug. 11, 1998.
  • (a) Wu, B.-P.; Pang, M.-L.; Tan, T.-F.; Meng, J.-B. Spectrochim. Acta A 2013, 107, 39–45; (b) Wu, B.-P.; Pang, M.-L.; Tan, T.-F.; Meng, J.-B. J. Mol. Struct. 2013, 1032, 126–132.
  • Perez-Silanes, S.; Martinez-Esparza, J.; Oficialdegui, A. M.; Villanueva, H.; Orus, L.; Monge, A. J. Heterocycl. Chem. 2001, 38, 1025–1030.
  • Ishida, Y.; Ito, H.; Mori, D.; Saigo, K. Tetrahedron Lett. 2005, 46, 109–112.
  • Arrowsmith, J. E.; Cross, P. E.; Dickinson, R. P.; Thomas, G. N. US Patent 4956382 (A), Sep. 11, 1990.
  • Krayushkin, M. M.; Kalik, M. A.; Migulin, V. A. Russ. Chem. Rev. 2009, 78, 329–336.

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