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Green Synthetic Approach to 5-Substituted-1H-Tetrazoles via Recycle and Reuse of Tributyltin Chloride
Corresponding Author(s) : A. Sampath
Asian Journal of Chemistry,
Vol. 25 No. 1 (2013): Vol 25 Issue 1
Abstract
A simple, safe and efficient process for the recycle of tributyltin chloride from tributyltin hydroxide is developed and its reuse in the synthesis of 5-substituted-1H-tetrazoles is successfully demonstrated, which paved a way to reduce the toxic tin waste significantly. Recycling of tributyltin chloride is possible over six cycles without loss of its activity.
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- T.M. Klapotke, in eds.: R.E. and W. de Gruyter, Moderne Anorganische Chemie, Berlin, Germany, edn. 3, pp 99-104 (2007).
- (a) T.M. Klapotke, High Energy Density Materials, Springer: Berlin, Germany, pp. 85-122 (2007); (b) T. Fendt, N. Fischer, T.M. Klapotke and J. Stierstorfer, Inorg. Chem., 50, 1447 (2011).
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- R.J. Herr, Bioorg. Med. Chem., 10, 3379 (2002) and references cited therein.
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- (a) J.T. Jagatap, K.B. Shejule and D.P. Jaiswal, World J. Fish Marine Sci., 3, 100 (2011); (b) R. Adema-Hannes and J. Shenker, Environ. Toxicol. Chem., 27, 2131 (2008); (c) P. Dimitrion, J. Castritsi-Catharios and H. Miliou, Ecotoxicol. Environ. Saf., 54, 30 (2003); (d) R. Ogata, M. Omura, Y. Shimasaki, K. Kubo, Y. Oshima, S. Aou and N. Inoue, J. Toxicol. Environ. Health A., 63, 127 (2001).
- D.P. Curran, S. Hadida and S.Y. Kim, Tetrahedron, 55, 8997 (1999).
- G.X. Wang, B.P. Sun and C.H. Peng, Org. Process. Res. Dev., 15, 986 (2011).
- T. Kato and Y. Shida, US Patent 5484955 (2009).
- B.S. Jursic and B.W. LeBlanc, J. Heterocycl. Chem., 35, 405 (1998).
- S.J. Wittenberger and B.G. Donner, J. Org. Chem., 58, 4139 (1993).
- L.D. Hansen, E.J. Baca and P. Scheiner, J. Heterocycl. Chem., 7, 991 (1970).
- E. Wiberg, N. Wiberg and A.F. Holleman, The Nitrogen Group. Inorganic Chemistry, Academic Press. p. 625 (2001).
- J.V. Duncia, M.E. Pierce and J.B. Santella III, J. Org. Chem., 56, 2395 (1991).
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References
T.M. Klapotke, in eds.: R.E. and W. de Gruyter, Moderne Anorganische Chemie, Berlin, Germany, edn. 3, pp 99-104 (2007).
(a) T.M. Klapotke, High Energy Density Materials, Springer: Berlin, Germany, pp. 85-122 (2007); (b) T. Fendt, N. Fischer, T.M. Klapotke and J. Stierstorfer, Inorg. Chem., 50, 1447 (2011).
(a) R.H. Bradbury, C.P. Allott, M. Dennis, J.A. Girdwood, P.W. Kenny, J.S. Major, A.A. Oldham, A.H. Ratcliffe and J.E. Rivet, J. Med. Chem., 36, 1245 (1993); (b) M. Koyama, N. Ohtani, F. Kai, I. Moriguchi and S. Inouye, J. Med. Chem., 30, 552 (1987), (c) K. Raman, S.S. Parmer and S.P. Singh, J. Heterocycl. Chem., 17, 1137 (1980); (d) J.R. Maxwell, D.A. Wasdahl, A.C. Wolfson and V.I. Stenberg, J. Med. Chem., 27, 1565 (1984).
R.J. Herr, Bioorg. Med. Chem., 10, 3379 (2002) and references cited therein.
(a) D. Amantini, R. Beleggia, F. Fringuelli, F. Pizzo and L. Vaccoro, J. Org. Chem., 69, 2896 (2004); (b) T. Jin, F. Kitahara, S. Kamijo and Y. Yamamoto, Tetrahedron Lett., 49, 2824 (2008); (c) M. Nasrollahzadeh, D. Habibi, Z. Shahkarami and Y. Bayat, Tetrahedron, 65, 10715, 2009; (d) A.N. Chermahini, A. Teimouri, F. Momenbeik, A. Zarei, Z. Dalirnasab, A. Ghaedi and M. Roosta, J. Heterocycl. Chem., 47, 913 (2010); (e) Y. Zhou, C. Yao, R. Ni and G. Yang, Synth. Commun., 40, 2624 (2010).
(a) S.J. Wittenberger, Org. Prep. Proced. Int., 26, 499 (1994); (b) In Comprehensive Heterocyclic Chemistry II, R.N. Butler, A.R. Katritzky, C.W. Rees, E.F.V. Scriven, Pergamon: Oxford, Vol. 4, p. 621 (1996).
D.J. Carini, J.V. Duncia, P.E. Aldrich, A.T. Chui, A.L. Johnson, M.E. Pierce, W.A. Price, J.B. Santella III, G.J. Wells, R.R. Wexler, P.C. Wong, S.E. Yoo and P.B.M.W.M. Timmermans, J. Med. Chem., 34, 2525 (1991).
(a) I. Saxena, A. Nath and M. Prasad, US Patent 7943794 B2 ( 2011); (b) P. Buhlmayer, F. Ostermayer and T. Schmidlin, US Patent 5399578 (1995); (c) U. Beutler, M. Boehm, P.C. Fuenfschilling, T. Heinz, J.P. Mutz, U. Onken, M. Mueller and W. Zaugg, Org. Proc. Res. Dev., 11, 892 (2007); (d) R.R. Soni, S.L. Vasoya, R.C. Ghotikar, A.K. Pandey
and H.R. Shah, US Patent 7923567 (2011); (e) Y. Kumar, K.V. Ramana, M. Prasad, A. Nath, S. Sathyanarayana and B. Vijayaraghavan, WO Patent 2005/051929 A1 (2005); (f) P.B. Deshpande, P. Luthra, A. Pandey, WO Patent 2007/054965 A2 ( 2007); (g) K.V.V.P. Rao, R. Dandala, V.K. Handa, I.V.S. Rao, A. Rani and A. Naidu, Syn. Commun., 37, 2897 (2007); (h) T. Naka, K. Nishikawa and T. Kato, US Patent 5196444 (1993).
(a) J.T. Jagatap, K.B. Shejule and D.P. Jaiswal, World J. Fish Marine Sci., 3, 100 (2011); (b) R. Adema-Hannes and J. Shenker, Environ. Toxicol. Chem., 27, 2131 (2008); (c) P. Dimitrion, J. Castritsi-Catharios and H. Miliou, Ecotoxicol. Environ. Saf., 54, 30 (2003); (d) R. Ogata, M. Omura, Y. Shimasaki, K. Kubo, Y. Oshima, S. Aou and N. Inoue, J. Toxicol. Environ. Health A., 63, 127 (2001).
D.P. Curran, S. Hadida and S.Y. Kim, Tetrahedron, 55, 8997 (1999).
G.X. Wang, B.P. Sun and C.H. Peng, Org. Process. Res. Dev., 15, 986 (2011).
T. Kato and Y. Shida, US Patent 5484955 (2009).
B.S. Jursic and B.W. LeBlanc, J. Heterocycl. Chem., 35, 405 (1998).
S.J. Wittenberger and B.G. Donner, J. Org. Chem., 58, 4139 (1993).
L.D. Hansen, E.J. Baca and P. Scheiner, J. Heterocycl. Chem., 7, 991 (1970).
E. Wiberg, N. Wiberg and A.F. Holleman, The Nitrogen Group. Inorganic Chemistry, Academic Press. p. 625 (2001).
J.V. Duncia, M.E. Pierce and J.B. Santella III, J. Org. Chem., 56, 2395 (1991).
D.B. Reitz, US Patent 5196537 (1993).