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One-pot Synthesis of 2-Alkylthio-1,3,4-oxadiazole and Bis-(1,3,4-oxadiazole-2-yl)thio alkyl Derivatives from Acid Hydrazides and CS2
Corresponding Author(s) : Mohammad Soleiman-Beigi
Asian Journal of Chemistry,
Vol. 25 No. 9 (2013): Vol 25 Issue 9
Abstract
An efficient and one-pot method for synthesis of 2-alkylthio-1,3,4-oxadiazole derivatives in mild conditions is described. Some novel derivatives such as bis-1,3,4-oxadiazole analogs are also synthesized.
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- J.P. Zhu and H. Bienayme, Multicomponent Reactions, Wiley-VCH: Weinheim (2005).
- L.F. Tietze, A. Heins, M. Soleiman-Beigi and C. Raith, Heterocycles, 77, 1123 (2009).
- S. Balalaie, M. Soleiman-Beigi and F. Rominger, J. Iran. Chem. Soc., 2, 319 (2005).
- J. Wang, R. Wang, J. Yang, Z. Zheng, M.D. Carducci, T. Cayou, N. Peyghambarian and G.E. Jabbour, J. Am. Chem. Soc., 123, 6179 (2001).
- C.J. Chen, B.-A. Song, S. Yang, G.-F. Xu, P.S. Bhadury, L.-H. Jin, D.-Y. Hu, Q.-Z. Li, F. Liu, W. Xue, P. Lu and Z. Chen, Bioorg. Med. Chem., 15, 3981 (2007).
- A.G. Ghattas, H.A. El-sherief, A.E. Abdelrahman and A. M. Mahmoud, Pharmazie, 37, 410 (1982).
- X.J. Zou, L.H. Lai, G.Y. Jin and Z.X. Zhang, J. Agric. Food Chem., 50, 3757 (2002).
- S. Aboraia, H.M. Abdel-Rahman, N.M. Mahfouz and M.A. El-Gendy, Bioorg. Med. Chem., 14, 1236 (2006).
- M.M. Burbuliene, V. Jakubkiene, G. Mekuskiene, E. Udrenaite, R. Smicius and P. Vainilavicius, Farmaco, 59, 767 (2004).
- D.H. Boschelli, D.T. Connor, D.A. Bornemeier, R.D. Dyer, J.A. Kennedy, P.J. Kuipers, G.C. Okonkwo, D.J. Schrier and C.D. Wright, J. Med. Chem., 36, 1802 (1993).
- G.C. Ramaprasad, B. Kallurya, B.S. Kumar and R.K. Hunnur, Eur. J. Med. Chem., 45, 4587 (2010).
- F. Aydogan, Z. Turgut, N. Olcay and S.S. Erdem, Turk. J. Chem., 26, 159 (2002).
- D.A. Charistos, G.V. Vagenes, L.C. Tzavellas, C.A. Tsoleridis and N.A. Rodios, J. Heterocycl. Chem., 31, 1593 (1994).
- C.A. Tsoleridis, D.A. Charistos and G.V. Vagenes, J. Heterocycl. Chem., 34, 1715 (1997).
- M.S.R. Murty, R.V. Rao, K.R. Ram, N.R. Reddy, J.S. Yadav and B. Sridhar, Synth. Commun., 40, 2914 (2010).
- M.G. Mamolo, D. Zampieri, L. Vio, M. Fermeglia, M. Ferrone, S. Pricl and G. Scialino, Bioorg. Med. Chem., 13, 3797 (2005).
- A. Rutavicius, S. Valyulene and Z. Kuodis, Chem. Heterocycl. Comp., 38, 852 (2002).
- N. Jain, D.P. Pathak, P. Mishra and S. Jain, J. Iran. Chem. Soc., 6, 77 (2009).
- T. Akhtar, S. Hameed, N.A. Al-Masoudi, R. Loddo and P.L. Colla, Acta Pharm., 58, 135 (2008).
- S.V. Bhandari, K.G. Bothara, M.K. Raut, A.A. Patil, A.P. Sarkate and V.J. Mokale, Bioorg. Med. Chem., 16, 1822 (2008).
- M. Koparir, A. Çetin and A. Cansiz, Molecules, 10, 475 (2005).
- R. Smicius, V. Jakabkiene, M.M. Burbuluiene and P. Vainlavicius, Monatsh. Chem., 133, 173 (2002).
- A.P. Andrushko, A.M. Demchenko, A.N. Krasovskii, E.B. Rusanov, A.N. Chernega and M.O. Lozinskii, Russ. J. Gen. Chem., 71, 1754 (2001).
- R. Patil and J.S. Biradar, Indian J. Chem., 38B, 76 (1999).
- Q.-Z. Zheng, X.-M. Zhang, Y. Xu, K. Cheng, Q.-C. Jiao and H.-L. Zhu, Bioorg. Med. Chem., 18, 7836 (2010).
- H.P. Shah, B.R. Shah and N.K. Undavia, Indian J. Chem., 37B, 180 (1998).
- M. Saitoh, J.E. Kunitomo, Y. Kimura, H. Hayase, N. Kobayashi, T. Uchiyama, T. Kawamoto, C. Tanaka, D. Mol, D.R. Dougan, G.S. Textor, G.P. Snell and F. Itoh, Bioorg. Med. Chem., 17, 2017 (2009).
- E. Hoggsrth, J. Chem. Soc., 4811 (1952).
- M.A. Khali, S.M. El-Khawass and M.G. Kassem, Sci. Pharm., 48, 344 (1980).
- M. Belkadi and A.A. Othman, ARKIVOC, 183 (2006).
- D.E. Horning and J.M. Muchowski, Can. J. Chem., 50, 3079 (1972).
- B. Movassagh and M. Soleiman-Beigi, Monatsh. Chem., 140, 409 (2009).
- S.T. Kadam and S.S. Kim, Green Chem., 12, 94 (2010).
- M. Zareef, R. Iqbal, B. Mirza, M.K. Khan, A. Manan, F. Asim and W.S. Khana, ARKIVOC, 141 (2008).
References
J.P. Zhu and H. Bienayme, Multicomponent Reactions, Wiley-VCH: Weinheim (2005).
L.F. Tietze, A. Heins, M. Soleiman-Beigi and C. Raith, Heterocycles, 77, 1123 (2009).
S. Balalaie, M. Soleiman-Beigi and F. Rominger, J. Iran. Chem. Soc., 2, 319 (2005).
J. Wang, R. Wang, J. Yang, Z. Zheng, M.D. Carducci, T. Cayou, N. Peyghambarian and G.E. Jabbour, J. Am. Chem. Soc., 123, 6179 (2001).
C.J. Chen, B.-A. Song, S. Yang, G.-F. Xu, P.S. Bhadury, L.-H. Jin, D.-Y. Hu, Q.-Z. Li, F. Liu, W. Xue, P. Lu and Z. Chen, Bioorg. Med. Chem., 15, 3981 (2007).
A.G. Ghattas, H.A. El-sherief, A.E. Abdelrahman and A. M. Mahmoud, Pharmazie, 37, 410 (1982).
X.J. Zou, L.H. Lai, G.Y. Jin and Z.X. Zhang, J. Agric. Food Chem., 50, 3757 (2002).
S. Aboraia, H.M. Abdel-Rahman, N.M. Mahfouz and M.A. El-Gendy, Bioorg. Med. Chem., 14, 1236 (2006).
M.M. Burbuliene, V. Jakubkiene, G. Mekuskiene, E. Udrenaite, R. Smicius and P. Vainilavicius, Farmaco, 59, 767 (2004).
D.H. Boschelli, D.T. Connor, D.A. Bornemeier, R.D. Dyer, J.A. Kennedy, P.J. Kuipers, G.C. Okonkwo, D.J. Schrier and C.D. Wright, J. Med. Chem., 36, 1802 (1993).
G.C. Ramaprasad, B. Kallurya, B.S. Kumar and R.K. Hunnur, Eur. J. Med. Chem., 45, 4587 (2010).
F. Aydogan, Z. Turgut, N. Olcay and S.S. Erdem, Turk. J. Chem., 26, 159 (2002).
D.A. Charistos, G.V. Vagenes, L.C. Tzavellas, C.A. Tsoleridis and N.A. Rodios, J. Heterocycl. Chem., 31, 1593 (1994).
C.A. Tsoleridis, D.A. Charistos and G.V. Vagenes, J. Heterocycl. Chem., 34, 1715 (1997).
M.S.R. Murty, R.V. Rao, K.R. Ram, N.R. Reddy, J.S. Yadav and B. Sridhar, Synth. Commun., 40, 2914 (2010).
M.G. Mamolo, D. Zampieri, L. Vio, M. Fermeglia, M. Ferrone, S. Pricl and G. Scialino, Bioorg. Med. Chem., 13, 3797 (2005).
A. Rutavicius, S. Valyulene and Z. Kuodis, Chem. Heterocycl. Comp., 38, 852 (2002).
N. Jain, D.P. Pathak, P. Mishra and S. Jain, J. Iran. Chem. Soc., 6, 77 (2009).
T. Akhtar, S. Hameed, N.A. Al-Masoudi, R. Loddo and P.L. Colla, Acta Pharm., 58, 135 (2008).
S.V. Bhandari, K.G. Bothara, M.K. Raut, A.A. Patil, A.P. Sarkate and V.J. Mokale, Bioorg. Med. Chem., 16, 1822 (2008).
M. Koparir, A. Çetin and A. Cansiz, Molecules, 10, 475 (2005).
R. Smicius, V. Jakabkiene, M.M. Burbuluiene and P. Vainlavicius, Monatsh. Chem., 133, 173 (2002).
A.P. Andrushko, A.M. Demchenko, A.N. Krasovskii, E.B. Rusanov, A.N. Chernega and M.O. Lozinskii, Russ. J. Gen. Chem., 71, 1754 (2001).
R. Patil and J.S. Biradar, Indian J. Chem., 38B, 76 (1999).
Q.-Z. Zheng, X.-M. Zhang, Y. Xu, K. Cheng, Q.-C. Jiao and H.-L. Zhu, Bioorg. Med. Chem., 18, 7836 (2010).
H.P. Shah, B.R. Shah and N.K. Undavia, Indian J. Chem., 37B, 180 (1998).
M. Saitoh, J.E. Kunitomo, Y. Kimura, H. Hayase, N. Kobayashi, T. Uchiyama, T. Kawamoto, C. Tanaka, D. Mol, D.R. Dougan, G.S. Textor, G.P. Snell and F. Itoh, Bioorg. Med. Chem., 17, 2017 (2009).
E. Hoggsrth, J. Chem. Soc., 4811 (1952).
M.A. Khali, S.M. El-Khawass and M.G. Kassem, Sci. Pharm., 48, 344 (1980).
M. Belkadi and A.A. Othman, ARKIVOC, 183 (2006).
D.E. Horning and J.M. Muchowski, Can. J. Chem., 50, 3079 (1972).
B. Movassagh and M. Soleiman-Beigi, Monatsh. Chem., 140, 409 (2009).
S.T. Kadam and S.S. Kim, Green Chem., 12, 94 (2010).
M. Zareef, R. Iqbal, B. Mirza, M.K. Khan, A. Manan, F. Asim and W.S. Khana, ARKIVOC, 141 (2008).