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Copyright (c) 2014 M.A. Bhat1, H.A. Ghabbour1, C.S.C. Kumar2, H.K. Fun1
This work is licensed under a Creative Commons Attribution 4.0 International License.
New and Efficient Synthesis of N-(4-Substituted phenyl)-5-(pyridin-4-yl)-1,3,4-oxadiazol-2-amines
Corresponding Author(s) : M.A. Bhat1
Asian Journal of Chemistry,
Vol. 26 No. 24 (2014)
Abstract
The reaction of 2-isonicotinoyl-N-arylhydrazinecarbothioamide (2a-c) with chloroacetic acid in presence of anhydrous sodium acetate in absolute ethanol yields, in each case, a single product. The single crystal X-ray analysis confirmed the structure of these products as N-(4-aryl)-5-(pyridine-4-yl)-1,3,4-oxadiazol-2-amines (4a-c).
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- Y.L. Janin, Bioorg. Med. Chem., 15, 2479 (2007).
- A.E. Wilder-Smith, Arzneimittelforschung, 16, 1034 (1966).
- M.G. Mamolo, D. Zampieri, L. Vio, M. Fermeglia, M. Ferrone, S. Pricl, G. Scialino and E. Banfi, Bioorg. Med. Chem., 13, 3797 (2005).
- T.M. Tan, Y. Chen, K.H. Kong, J. Bai, Y. Li, S.G. Lim, T.H. Ang and Y. Lam, Antiviral Res., 71, 7 (2006).
- M.T.H. Khan, M.I. Choudhary, K.M. Khan, M. Rani and Atta-ur-Rahman, Bioorg. Med. Chem., 13, 3385 (2005).
- S.L. Gaonkar, K.M.L. Rai and B. Prabhuswamy, Eur. J. Med. Chem., 41, 841 (2006).
- V.L. Pachhamia and A.R. Parekh, J. Indian Chem. Soc., 66, 250 (1989).
- J.T. Palmer, B.L. Hirschbein, H. Cheung, J. Mc Carter, J.W. Janc, Z.W. Yu and G. Wesolowski, Bioorg. Med. Chem. Lett., 16, 2909 (2006).
- Y. Li, J. Liu, H. Zhang, X. Yang and Z. Liu, Bioorg. Med. Chem. Lett., 16, 2278 (2006).
- A.S. Aboraia, H.M. Abdel-Rahman, N.M. Mahfouz and M.A. El-Gendy, Bioorg. Med. Chem., 14, 1236 (2006).
- H.A. Abdel-Aziz, M.A. Bhat, M. Ghazzali, Phosphorus, Sulphur Silicon Rel. Elem., 189, 1328 (2014).
- M. Al-Talib, H. Tashtoush and N. Odeh, Synth. Commun., 20, 1811 (1990).
- S. Sharma, V.K. Srivastava and A. Kumar, Eur. J. Med. Chem., 37, 689 (2002).
- C.T. Brain, J.M. Paul, Y. Loong and P.J. Oakley, Tetrahedron Lett., 40, 3275 (1999).
- S. Maghari, S. Ramezanpour, F. Darvish, S. Balalaie, F. Rominger and H.R. Bijanzadeh, Tetrahedron, 69, 2075 (2013).
- G. Prabhu and V.V. Sureshbabu, Tetrahedron Lett., 53, 4232 (2012).
- Bruker APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Winconsin, USA (2009).
- G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008).
- M.S. Yar and M.W. Akhtar, Acta Pol. Pharm., 66, 393 (2009).
- X. Wang, W. Wang, H.X. Liu, M.Y. Tan and M. Li, Acta Crystallogr. C, 51, 1585 (1995).
- C.S. de Oliveira, B.F. Lira, J.M. Barbosa-Filho, J.G.F. Lorenzo and P.F. de Athayde-Filho, Molecules, 17, 10192 (2012).
References
Y.L. Janin, Bioorg. Med. Chem., 15, 2479 (2007).
A.E. Wilder-Smith, Arzneimittelforschung, 16, 1034 (1966).
M.G. Mamolo, D. Zampieri, L. Vio, M. Fermeglia, M. Ferrone, S. Pricl, G. Scialino and E. Banfi, Bioorg. Med. Chem., 13, 3797 (2005).
T.M. Tan, Y. Chen, K.H. Kong, J. Bai, Y. Li, S.G. Lim, T.H. Ang and Y. Lam, Antiviral Res., 71, 7 (2006).
M.T.H. Khan, M.I. Choudhary, K.M. Khan, M. Rani and Atta-ur-Rahman, Bioorg. Med. Chem., 13, 3385 (2005).
S.L. Gaonkar, K.M.L. Rai and B. Prabhuswamy, Eur. J. Med. Chem., 41, 841 (2006).
V.L. Pachhamia and A.R. Parekh, J. Indian Chem. Soc., 66, 250 (1989).
J.T. Palmer, B.L. Hirschbein, H. Cheung, J. Mc Carter, J.W. Janc, Z.W. Yu and G. Wesolowski, Bioorg. Med. Chem. Lett., 16, 2909 (2006).
Y. Li, J. Liu, H. Zhang, X. Yang and Z. Liu, Bioorg. Med. Chem. Lett., 16, 2278 (2006).
A.S. Aboraia, H.M. Abdel-Rahman, N.M. Mahfouz and M.A. El-Gendy, Bioorg. Med. Chem., 14, 1236 (2006).
H.A. Abdel-Aziz, M.A. Bhat, M. Ghazzali, Phosphorus, Sulphur Silicon Rel. Elem., 189, 1328 (2014).
M. Al-Talib, H. Tashtoush and N. Odeh, Synth. Commun., 20, 1811 (1990).
S. Sharma, V.K. Srivastava and A. Kumar, Eur. J. Med. Chem., 37, 689 (2002).
C.T. Brain, J.M. Paul, Y. Loong and P.J. Oakley, Tetrahedron Lett., 40, 3275 (1999).
S. Maghari, S. Ramezanpour, F. Darvish, S. Balalaie, F. Rominger and H.R. Bijanzadeh, Tetrahedron, 69, 2075 (2013).
G. Prabhu and V.V. Sureshbabu, Tetrahedron Lett., 53, 4232 (2012).
Bruker APEX2, SAINT and SADABS, Bruker AXS Inc., Madison, Winconsin, USA (2009).
G.M. Sheldrick, Acta Crystallogr. A, 64, 112 (2008).
M.S. Yar and M.W. Akhtar, Acta Pol. Pharm., 66, 393 (2009).
X. Wang, W. Wang, H.X. Liu, M.Y. Tan and M. Li, Acta Crystallogr. C, 51, 1585 (1995).
C.S. de Oliveira, B.F. Lira, J.M. Barbosa-Filho, J.G.F. Lorenzo and P.F. de Athayde-Filho, Molecules, 17, 10192 (2012).