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Novel Synthesis of 5-Oxo-2-thioxo-2,5-dihydro-3-thiophenecarboxylate Derivatives in Non-Aqueous Medium
Corresponding Author(s) : Nitin Srivastava
Asian Journal of Chemistry,
Vol. 31 No. 1 (2019): Vol 31 Issue 1
Abstract
A novel synthetic method of synthesis of 5-oxo-2-thioxo-2,5-dihydro-3-thiophenecarboxylate (rhodanine) derivative is being reported using primary amines and acetylenic ester, carbon disufide and Triton-B in non-aqueous medium.
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- S.K. Shukla, S.P. Singh, L.P. Awasthi and D.D. Mukherjee, Indian J. Pharm. Sci., 44, 153 (1982).
- B.B. Lohray, V. Bhushan, P.B. Rao, G.R. Madhavan, N. Murali, K.N. Rao, G.R. Madhavan, N. Murali, K.N. Rao, K. Anantha Reddy, B.M. Rajesh, P. Ganpathy Reddy, R. Chakrabarti and R. Rajagopalan, Bioorg. Med. Chem. Lett., 7, 785 (1997); https://doi.org/10.1016/S0960-894X(97)00118-2.
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- C.L. Lee and M.M. Sim, Tetrahedron Lett., 41, 5729 (2000); https://doi.org/10.1016/S0040-4039(00)00866-2.
- F.C. Brown, Chem. Rev., 61, 463 (1961); https://doi.org/10.1021/cr60213a002.
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- A. Alizadeh, F. Movahedi, H. Masrouri and L.-G. Zhu, Synthesis, 3431 (2006); https://doi.org/10.1055/s-2006-950234.
- A. Alizadeh, F. Movahedi and A.A. Esmaili, Tetrahedron Lett., 47, 4469 (2006); https://doi.org/10.1016/j.tetlet.2006.04.040.
- J. Liu, Y. Zhou, Y. Wu, X. Li and A.S.C. Chan, Tetrahedron Asymm., 19, 832 (2008); https://doi.org/10.1016/j.tetasy.2008.03.015.
- D. Kaminskyy, A. Kryshchyshyn and R. Lesyk, Expert Opin. Drug Discov., 12, 1233 (2017); https://doi.org/10.1080/17460441.2017.1388370.
- S.S. Alneyadi, Heterocycles, 96, 803 (2018); https://doi.org/10.3987/REV-17-878.
- T. Tomasic and L.P. Masiè, Expert Opin. Drug Discov., 7, 549 (2012); https://doi.org/10.1517/17460441.2012.688743.
- T. Tomasic and L.P. Masiè, Curr. Med. Chem., 16, 1596 (2009); https://doi.org/10.2174/092986709788186200.
- A. Alizadeh, S. Rostamnia, N. Zohreh and R. Hosseinpour, Tetrahedron Lett., 50, 1533 (2009); https://doi.org/10.1016/j.tetlet.2008.12.107.
References
Y. Inamori, Y. Okamoto, Y. Takegawa, H. Tsujibo, Y. Sakagami, Y. Kumeda, M. Shibata and A. Numata, Biosci. Biotechnol. Biochem., 62, 1025 (1998); https://doi.org/10.1271/bbb.62.1025.
J. Miao, C.-J. Zheng, L.-P. Sun, M.-X. Song, L.-L. Xu and H.-R. Piao, Med. Chem. Res., 22, 4125 (2013); https://doi.org/10.1007/s00044-012-0417-z.
P. Mitra and A.S. Mitra, J. Indian Chem. Soc., 61, 77 (1984).
A.A. Khalek, C.R. Ashby Jr., B.A. Patel, T.T. Talele and M.N. Seleem, PLoS One, 11, e0164227 (2016); https://doi.org/10.1371/journal.pone.0164227.
W. Sing, C.L. Lee, S.L. Yeo, S.P. Lim and M.M. Sim, Bioorg. Med. Chem. Lett., 11, 91 (2001); https://doi.org/10.1016/S0960-894X(00)00610-7.
M.G. Orchard, J.C. Neuss, C.M. Galley, A. Carr, D.W. Porter, P. Smith, D.I.C. Scopes, D. Haydon, K. Vousden, C.R. Stubberfield, K. Young and M. Page, Bioorg. Med. Chem. Lett., 14, 3975 (2004); https://doi.org/10.1016/j.bmcl.2004.05.050.
N.S. Cutshall, C. O’ Day and M. Prezhdo, Bioorg. Med. Chem. Lett., 15, 3374 (2005); https://doi.org/10.1016/j.bmcl.2005.05.034.
J.H. Ahn, S.J. Kim, W.S. Park, S.Y. Cho, J.D. Ha, S.S. Kim, S.K. Kang, D.G. Jeong, S.-K. Jung, S.-H. Lee, H.M. Kim, S.K. Park, K.H. Lee, C.W. Lee, S.E. Ryu and J.-K. Choi, Bioorg. Med. Chem. Lett., 16, 2996 (2006); https://doi.org/10.1016/j.bmcl.2006.02.060.
E.B. Grant, D. Guiadeen, E.Z. Baum, B.D. Foleno, D.A. Montenegro, H. Jin, E.A. Nelson, K. Bush and D.J. Hlasta, Bioorg. Med. Chem. Lett., 10, 2179 (2000); https://doi.org/10.1016/S0960-894X(00)00444-3.
N.J. Gaikwad and P. Gautam, Indian J. Heterocycl. Chem., 12, 181 (2002).
S.K. Shukla, S.P. Singh, L.P. Awasthi and D.D. Mukherjee, Indian J. Pharm. Sci., 44, 153 (1982).
B.B. Lohray, V. Bhushan, P.B. Rao, G.R. Madhavan, N. Murali, K.N. Rao, G.R. Madhavan, N. Murali, K.N. Rao, K. Anantha Reddy, B.M. Rajesh, P. Ganpathy Reddy, R. Chakrabarti and R. Rajagopalan, Bioorg. Med. Chem. Lett., 7, 785 (1997); https://doi.org/10.1016/S0960-894X(97)00118-2.
S.P. Singh, S.S. Parmar, K. Raman and V.I. Stenberg, Chem. Rev., 81, 175 (1981); https://doi.org/10.1021/cr00042a003.
C.L. Lee and M.M. Sim, Tetrahedron Lett., 41, 5729 (2000); https://doi.org/10.1016/S0040-4039(00)00866-2.
F.C. Brown, Chem. Rev., 61, 463 (1961); https://doi.org/10.1021/cr60213a002.
W.-D. Rudorf and R. Schwarz, Hetrocycles, 24, 3459 (1986); https://doi.org/10.3987/R-1986-12-3459.
S. Gabillet, D. Lecercle, O. Loreau, M. Carboni, S. Dezard, J. Gomis and M. Taran, Org. Lett., 9, 3925 (2007); https://doi.org/10.1021/ol701563e.
A. Alizadeh, F. Movahedi, H. Masrouri and L.-G. Zhu, Synthesis, 3431 (2006); https://doi.org/10.1055/s-2006-950234.
A. Alizadeh, F. Movahedi and A.A. Esmaili, Tetrahedron Lett., 47, 4469 (2006); https://doi.org/10.1016/j.tetlet.2006.04.040.
J. Liu, Y. Zhou, Y. Wu, X. Li and A.S.C. Chan, Tetrahedron Asymm., 19, 832 (2008); https://doi.org/10.1016/j.tetasy.2008.03.015.
D. Kaminskyy, A. Kryshchyshyn and R. Lesyk, Expert Opin. Drug Discov., 12, 1233 (2017); https://doi.org/10.1080/17460441.2017.1388370.
S.S. Alneyadi, Heterocycles, 96, 803 (2018); https://doi.org/10.3987/REV-17-878.
T. Tomasic and L.P. Masiè, Expert Opin. Drug Discov., 7, 549 (2012); https://doi.org/10.1517/17460441.2012.688743.
T. Tomasic and L.P. Masiè, Curr. Med. Chem., 16, 1596 (2009); https://doi.org/10.2174/092986709788186200.
A. Alizadeh, S. Rostamnia, N. Zohreh and R. Hosseinpour, Tetrahedron Lett., 50, 1533 (2009); https://doi.org/10.1016/j.tetlet.2008.12.107.