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Copyright (c) 2014 Zhen-Li Min*, Ting-Zi Yin, Xia-Min Hu
This work is licensed under a Creative Commons Attribution 4.0 International License.
A Facile One-Pot Synthesis of 2,4,6-Triarylpyridine in DMSO
Corresponding Author(s) : Zhen-Li Min*
Asian Journal of Chemistry,
Vol. 26 No. 23 (2014)
Abstract
A facile, efficient and practical method for the one-pot synthesis of 2,4,6-triarylpyridines starting from acetophenones, aryl aldehydes and ammonium acetate by the use of catalytic amounts of 40 % potassium hydroxide in dimethyl sulfoxide is presented. The present methodology offers attractive features such as the ease of workup, short reaction time and good yields of the products and it does not need any complex catalyst.
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- (a) B.S. Dawane, S.G. Konda and R.B. Bhosale, Der. Pharma Chem., 2, 251 (2010); (b) R. Rambabu, Y.R. Prasad and S. Vidyadhara, Curr. Pharma Res., 3, 799 (2013); (c) N.K. Ladani, M.P. Patel and R.G. Patel, Indian J. Chem., 48B, 261 (2009).
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- (a) E.C. Constable, C.E. Housecroft, M. Neuburger, D. Phillips, P.R. Raithby, E. Schofield, E. Sparr, D.A. Tocher, M. Zehnder and Y. Zimmermann, J. Chem. Soc., Dalton Trans., 2219 (2008); (b) W.V. Cave, M.J. Hardie, B.A. Roberts and C.L. Raston, Eur. J. Org. Chem., 3227 (2001); (c) R.K.R. Jetti, A. Nangia, F. Xue and T.C.W. Mak, Chem. Commun., 37, 919 (2001); (d) P. Rajput, N.J.P. Subhashini and S. Raj, J. Sci. Res., 2, 337 (2010).
- P.V. Shinde, V.B. Labade, J.B. Gujar, B.B. Shingate and M.S. Shingare, Tetrahedron Lett., 53, 1523 (2012).
- (a) A.R. Katritzky, A.A.A. Abdel-Fattah, D.O. Tymoshenko and S.A. Essawy, Synthesis, 2114 (1999); (b) P.V. Shinde, V.B. Labade, J.B. Gujar, B.B. Shingate and M.S. Shingare, Tetrahedron Lett., 53, 1523 (2012).
- (a) L.F. Tietze, Chem. Rev., 96, 115 (1996); (b) A. Chanda and V.V. Fokin, Chem. Rev., 109, 725 (2009).
- S. Tu, T. Li, F. Shi, F. Fang, S. Zhu, X. Wei and Z. Zong, Chem. Lett., 34, 732 (2005).
- P.G. Ingole, S.V. Jadhav and H.C. Bajaj, Int. J. Chem. Technol. Res., 2, 289 (2010).
- (a) M.M. Heravi, K. Bakhtiari, Z. Daroogheha and F.F. Bamoharram, Catal. Commun., 8, 1991 (2007); (b) J. Safari, Z. Zarnegar and M.B. Borujeni, Chemical Papers, 67, 688 (2013); (c) P.V. Shinde, V.B. Labade, J.B. Gujar, B.B. Shingate and B.S. Shingare, Tetrahedron Lett., 53, 1523 (2012).
- (a) N.M. Smith, C.L. Raston, C.B. Smith and A.N. Sobolev, Green Chem., 9, 1185 (2007); (b) A. Winter, A.M.J. Vanden Berg, R. Hoogenboom, G. Kickelbick and U.S. Schubert, Synthesis, 2873 (2006).
- (a) R. Shankar, A.K. Jha, U.S. Singh and K. Hajela, Tetrahedron Lett., 47, 3077 (2006); (b) W. Parasuk and V. Parasuk, J. Org. Chem., 73, 9388 (2008); (c) K.N. Shavrin, V.D. Gvozdev and O.M. Nefedov, Mendeleev Commun., 23, 140 (2013); (d) S. Paladhi, A. Chauhan, K. Dhara, A.K. Tiwari and J. Dash, Green Chem., 14, 2990 (2012).
- S. Senda, K. Hirota, G.N. Yang and M. Shirahashi, Yakugaku Zasshi, 91, 1372 (1971).
References
(a) B.S. Dawane, S.G. Konda and R.B. Bhosale, Der. Pharma Chem., 2, 251 (2010); (b) R. Rambabu, Y.R. Prasad and S. Vidyadhara, Curr. Pharma Res., 3, 799 (2013); (c) N.K. Ladani, M.P. Patel and R.G. Patel, Indian J. Chem., 48B, 261 (2009).
(a) A. Basnet, P. Thapa, R. Karki, Y. Na, Y. Jahng, B. Jeong, T.C. Jeong, C. Lee and E. Lee, Bioorg. Med. Chem., 15, 4351 (2007); (b) P. Thapa, R. Karki, U. Thapa, Y. Jahng, M. Jung, J.M. Nam, Y. Na, Y. Kwon and E. Lee, Bioorg. Med. Chem., 18, 377 (2010); (c) R. Karki, P. Thapa, M.J. Kang, T.C. Jeong, J.M. Nam, H.-L. Kim, Y. Na, W.-J. Cho, Y. Kwon and E.-S. Lee, Bioorg. Med. Chem., 18, 3066 (2010); (d) P. Thapa, R. Karki, M. Yun, T.M. Kadayat, E. Lee, H.B. Kwon, Y. Na, W.-J. Cho, N.D. Kim, B.-S. Jeong, Y. Kwon and E.-S. Lee, Eur. J. Med. Chem., 52, 123 (2012); (e) R. Karki, P. Thapa, H.Y. Yoo, T.M. Kadayat, P.-H. Park, Y. Na, E. Lee, K.-H. Jeon, W.-J. Cho, H. Choi, Y. Kwon and E.-S. Lee, Eur. J. Med. Chem., 49, 219 (2012).
(a) E.C. Constable, C.E. Housecroft, M. Neuburger, D. Phillips, P.R. Raithby, E. Schofield, E. Sparr, D.A. Tocher, M. Zehnder and Y. Zimmermann, J. Chem. Soc., Dalton Trans., 2219 (2008); (b) W.V. Cave, M.J. Hardie, B.A. Roberts and C.L. Raston, Eur. J. Org. Chem., 3227 (2001); (c) R.K.R. Jetti, A. Nangia, F. Xue and T.C.W. Mak, Chem. Commun., 37, 919 (2001); (d) P. Rajput, N.J.P. Subhashini and S. Raj, J. Sci. Res., 2, 337 (2010).
P.V. Shinde, V.B. Labade, J.B. Gujar, B.B. Shingate and M.S. Shingare, Tetrahedron Lett., 53, 1523 (2012).
(a) A.R. Katritzky, A.A.A. Abdel-Fattah, D.O. Tymoshenko and S.A. Essawy, Synthesis, 2114 (1999); (b) P.V. Shinde, V.B. Labade, J.B. Gujar, B.B. Shingate and M.S. Shingare, Tetrahedron Lett., 53, 1523 (2012).
(a) L.F. Tietze, Chem. Rev., 96, 115 (1996); (b) A. Chanda and V.V. Fokin, Chem. Rev., 109, 725 (2009).
S. Tu, T. Li, F. Shi, F. Fang, S. Zhu, X. Wei and Z. Zong, Chem. Lett., 34, 732 (2005).
P.G. Ingole, S.V. Jadhav and H.C. Bajaj, Int. J. Chem. Technol. Res., 2, 289 (2010).
(a) M.M. Heravi, K. Bakhtiari, Z. Daroogheha and F.F. Bamoharram, Catal. Commun., 8, 1991 (2007); (b) J. Safari, Z. Zarnegar and M.B. Borujeni, Chemical Papers, 67, 688 (2013); (c) P.V. Shinde, V.B. Labade, J.B. Gujar, B.B. Shingate and B.S. Shingare, Tetrahedron Lett., 53, 1523 (2012).
(a) N.M. Smith, C.L. Raston, C.B. Smith and A.N. Sobolev, Green Chem., 9, 1185 (2007); (b) A. Winter, A.M.J. Vanden Berg, R. Hoogenboom, G. Kickelbick and U.S. Schubert, Synthesis, 2873 (2006).
(a) R. Shankar, A.K. Jha, U.S. Singh and K. Hajela, Tetrahedron Lett., 47, 3077 (2006); (b) W. Parasuk and V. Parasuk, J. Org. Chem., 73, 9388 (2008); (c) K.N. Shavrin, V.D. Gvozdev and O.M. Nefedov, Mendeleev Commun., 23, 140 (2013); (d) S. Paladhi, A. Chauhan, K. Dhara, A.K. Tiwari and J. Dash, Green Chem., 14, 2990 (2012).
S. Senda, K. Hirota, G.N. Yang and M. Shirahashi, Yakugaku Zasshi, 91, 1372 (1971).