The N-(1,3-oxathiol-2-ylidene)carboxamides have been synthesized in excellent yield in the reaction between alkyl bromide, acid chloride, and ammonium thiocyanate in the presence of catalytic amount of ZnO nanosheets (15 mol %) in water as a solvent at room temperature. The separation of product from the reaction mixture is very simple. Using NS-ZnO as a catalyst considerably improves the yield of the desired product in comparison with performing these reactions without catalyst. The catalyst shows good reusability.
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Multicomponent Reactions, Zhu, J.; Bienaymé, H., Eds.; Wiley-VCH: Weinheim, 2005.
Ramón, D. J.; Yus, M. Angew. Chem., Int. Ed. 2005, 44, 1602.
Zhu, J. Eur. J. Org. Chem. 2003, 1133.
Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem.–Eur. J. 2000, 6, 3321.
Dömling, A.; Ugi, I. Angew. Chem., Int. Ed. 2000, 39, 3168.
Koopmanschap, G.; Ruijter, E.; Orru, R. V. A. Beilstein J. Org. Chem. 2014, 10, 544.
Hulme, C.; Gore, V. Curr. Med. Chem. 2003, 10, 51.
Organic Synthesis in Water, Grieco, P. A., Ed.; Blackie Academic & Professional: Glasgow, 1998.
Green Chemistry: Frontiers in Benign Chemical Synthesis and Processes, Anastas, P.; Williamson, T. C., Eds.; Oxford University Press: New York, 1998.
Demko, Z. P.; Sharpless, K. B. J. Org Chem. 2001, 66, 7945.
Li, C. J. Chem Rev. 2005, 105, 3095.
Breslow, R. Acc. Chem. Res. 1991, 24, 159.
Li, C. J.; Chan, T. H. Organic Reactions in Aqueous Media; Wiley: New York, 1997.
Lindström, U. M. Chem. Rev. 2002, 102, 2751.
Kobayashi, S.; Manabe, K. Acc. Chem. Res. 2002, 35, 209.
Narayan, S.; Muldoon, J.; Finn, M. G.; Fokin, V. V.; Kolb, H. C.; Sharpless, K. B. Angew. Chem., Int. Ed. 2005, 44, 3275.
Pirrung, M. C. Chem. Eur. J. 2006, 12, 1312.
Polshettiwar, V.; Varma, R. S. Acc. Chem. Res. 2008, 41, 629.
Rostamizadeh, S.; Nojavan, M.; Aryan, R.; Isapoor, E.; Azad, M. J. Mol. Catal. A: Chem. 2013, 374–375, 102.
Beydoun, D.; Amal, R.; Low, G.; McEvoy, S. J. Nanopart. Res. 1999, 1, 439.
Comparelli, R.; Fanizza, E.; Curri, M. L.; Cozzoli, P. D.; Mascolo, G.; Agostiano, A. App. Catal., B 2005, 60, 1.
Moghaddam, F. M.; Saeidian, H. Mater. Sci. Eng., B 2007, 139, 265.
Mirjafary, Z.; Saeidian, H.; Sadeghi, A.; Moghaddam, F. M. Catal. Commun. 2008, 9, 299.
Gupta, M.; Paul, S.; Gupta, R.; Loupy, A. Tetrahedron Lett. 2005, 46, 4957.
Lietti, L.; Tronconi, E.; Forzatti, P. J. Mol. Catal. 1989, 55, 43.
Eskandari, K.; Karami, B.; Khodabakhshi, S. Chem. Heterocycl. Compd. 2015, 50, 1658. [Khim. Geterotsikl. Soed. 2014, 1807.]
Sabbaghan, M.; Anaraki Firooz, A.; Jan Ahmadi, V. J. Mol. Liq. 2012, 175, 135.
Mehrabi Matin, B.; Mortazavi, Y.; Khodadadi, A. A.; Abbasi, A.; Anaraki Firooz, A. Sens. Act. B: Chem. 2010, 151, 140.
Qi, L. In Encyclopedia of Surface and Colloid Science, Somasundaran, P., Ed.; 2nd ed.; CRC Press: Boca Raton, 2007, vol. 8, p. 6183.
Hosseini-Sarvari, M.; Tavakolian, M. Appl. Catal. A 2012, 441–442, 65.
Hosseini-Sarvari, M.; Sharghi, H.; Etemad, S. Helv. Chim. Acta 2008, 91,715.
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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2015, 51(9), 834–837
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Moradi, A.V. ZnO nanosheet-promoted synthesis of 1,3-oxathiol-2-ylidene derivatives using alkyl bromides in water. Chem Heterocycl Comp 51, 834–837 (2015). https://doi.org/10.1007/s10593-015-1783-5
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DOI: https://doi.org/10.1007/s10593-015-1783-5