A convenient, environmentally benign, metal- and catalyst-free protocol has been developed for the conversion of thioamides to the corresponding 1,2,4-thiadiazole derivatives with chloranil under ultrasound irradiation in water at room temperature. This paper describes a general procedure for the synthesis of different 1,2,4-thiadiazoles in excellent yield in short reaction time via sonochemistry.
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Castro, A.; Castaño, T.; Encinas, A.; Porcal, W.; Gil, C. Bioorg. Med. Chem. 2006, 14, 1644.
Iizawa, Y.; Okonogi, K.; Hayashi, R.; Iwahi, T.; Yamazaki, T.; Imada, A. Antimicrob. Agents Chemother.1993, 37, 100.
Kurzer, F. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1982, Vol. 32, p. 285.
Franz, J. E.; Dhingra, O. P. In Comprehensive Heterocyclic Chemistry; Katritzky, A. R.; Rees, C. W., Eds.; Oxford: Pergamon Press, 1984, Vol. 6, p. 463.
Huang, D.; Lüthi, U.; Kolb, P.; Edler, K.; Cecchini, M.; Audetat, S.; Barberis, A.; Caflisch, A. J. Med. Chem. 2005, 48, 5108.
Gurjar, A. S.; Andrisano, V.; Simone, A. D.; Velingkar, V. S. Bioorg. Chem. 2014, 57, 90.
Perlovich, G. L.; Proshin, A. N.; Volkova, T. V.; Petrova, L. N.; Bachurin, S. O. Mol. Pharmaceutics2012, 9, 2156.
Kumar, D.; Kumar, N. M.; Chang, K.-H.; Gupta, R.; Shah, K. Bioorg. Med. Chem. Lett. 2011, 21, 5897.
Katz, L. E. US Patent 19814263312.
Gay, W. A. US Patent 19804207089.
Romagnoli, R.; Baraldi, P. G.; Carrion, M. D.; Cruz-Lopez, O.; Preti, D.; Tabrizi, M. A.; Fruttarolo, F.; Heilmann, J.; Bermejo, J.; Estévez, F. Bioorg. Med. Chem. Lett. 2007, 17, 2844.
Leung-Toung, R.; Wodzinska, J.; Li, W.; Lowrie, J.; Kukreja, R.; Desilets, D.; Karimian, K.; Tam, T. F. Bioorg. Med. Chem. 2003, 11, 5529.
Van den Nieuwendijk, A. M. C. H.; Pietra, D.; Heitman, L.; Göblyös, A.; Ijzerman, A. P. J. Med. Chem.2004, 47, 663.
Leung-Toung, R.; Tam, T. F.; Wodzinska, J. M.; Zhao, Y.; Lowrie, J.; Simpson, C. D.; Karimian, K.; Spino, M. J. Med. Chem. 2005, 48, 2266.
Martinez, A.; Alonso, M.; Castro, A.; Pérez, C.; Moreno, F. J. J. Med. Chem. 2002, 45, 1292.
Unangst, P. C.; Shrum, G. P.; Connor, D. T.; Dyer, R. D.; Schrier, D. J. J. Med. Chem. 1992, 35, 3691.
Tam, T. F.; Leung-Toung, R.; Li, W.; Spino, M.; Karimian, K. Mini-Rev. Med. Chem. 2005, 5, 367.
MacLeod, A. M.; Baker, R.; Freedman, S. B.; Patel, S.; Merchant, K. J.; Roe, M.; Saunders, J. J. Med. Chem.1990, 33, 2052.
Decking, U. K. M.; Hartmann, M.; Rose, H.; Brückner, R.; Meil, J.; Schrader, J. Naunyn-Schmiedeberg's Arch. Pharmacol.1998, 358, 547.
Hartmann, M.; Decking, U. K. M.; Schrader, J. Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 358, 554.
Leung-Toung, R.; Tam, T. F.; Zhao, Y.; Simpson, C. D.; Li, W.; Desilets, D.; Karimian, K. J. Org. Chem.2005, 70, 6230.
Shutalev, A. D.; Kishko, E. A.; Alekseeva, S. G. Chem. Heterocycl. Compd.1997, 33, 352. [Khim. Geterotsikl. Soedin.1997, 412.]
Chauhan, S.; Chaudhary, P.; Singh, A. K.; Verma, P.; Srivastava, V.; Kandasamy, J. Tetrahedron Lett. 2018, 59, 272.
Vanajatha, G.; Reddy, V. P. Tetrahedron Lett.2016, 57, 2356.
Yoshimura, A.; Todora, A. D.; Kastern, B. J.; Koski, S. R.; Zhdankin, V. V. Eur. J. Org. Chem. 2014, 5149.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2020, 56(1), 123–126
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Chauhan, S., Verma, P., Mishra, A. et al. An Expeditious Ultrasound-Initiated Green Synthesis of 1,2,4-Thiadiazoles in Water. Chem Heterocycl Comp 56, 123–126 (2020). https://doi.org/10.1007/s10593-020-02632-5
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DOI: https://doi.org/10.1007/s10593-020-02632-5