Abstract
A convenient, one-pot, multicomponent synthesis of new (4-oxothiazolidine-2-ylidene)benzamide derivatives by unsymmetrical thioureas, various amines and methyl bromoacetate has been developed. These new compounds were characterized by IR, 1HNMR, 13CNMR, mass spectrometry, CHNS elemental analysis, and single-crystal X-ray analysis.
Similar content being viewed by others
References
F. Ghanbari Pirbasti, N.O. Mahmoodi, Mol. Divers. 20, 497 (2016)
M. Rashid, A. Husain, M. Shaharyar, R. Mishra, A. Hussain, O. Afzal, Eur. J. Med. Chem. 83, 630 (2014)
M.H. Sherif, I.M. Eldeen, E.O. Helal, Res Chem Intermed. 39, 3949 (2013)
A. Insuasty, J. Ramírez, M. Raimondi, C. Echeverry, J. Quiroga, R. Abonia, M. Nogueras, J. Cobo, M.V. Rodríguez, S.A. Zacchino, B. Insuasty, Molecules 18, 5482 (2013)
S. Koppireddi, J.R. Komsani, S. Avula, S. Pombala, S. Vasamsetti, S. Kotamraju, R. Yadla, Eur. J. Med. Chem. 66, 305 (2013)
G. Rajitha, V. Ravibabu, G. Ramesh, B. Rajitha, R. Jobina, B. Siddhardha, S. Vijaya, Laxmi. Res. Chem. Intermed. 41, 9703 (2015)
S. Kumar, H.R. Bhat, M.K. Kumawat, U.P. Singh, New J. Chem. 37, 581 (2013)
H.A. Ghabbour, A.A. Kadi, K.E.H. ElTahir, R.F. Angawi, H.I. El-Subbagh, Med. Chem. Res. 24, 3194 (2015)
I. Batool, A. Saeed, I. Zia Qureshi, S. Kalsoom, A. Razzaq, Res. Chem. Intermed. 42, 1139 (2016)
V. Murugesan, N. Makwana, R. Suryawanshi, R. Saxena, R. Tripathi, R. Paranjape, S. Kulkarni, S.B. Katti, Bioorg. Med. Chem. Lett. 22, 3159 (2014)
M. Singh, S.K. Singh, M. Gangwar, G. Nath, S.K. Singh, RSC Adv. 4, 19013 (2014)
V.S.R. Chunduru, V. Rajeswar Rao, Sulfur J. Chem. 6, 545 (2010)
K. Appalanaidu, T. Dadmal, N.J. Babu, R.M. Kumbhare, RSC Adv. 5, 88063 (2015)
S.V. Kumar, S. Muthusubramanian, S. Perumal, RSC Adv. 5, 90451 (2015)
T.R. Swaroop, H. Ila, K.S. Rangappa, Tetrahedron Lett. 54, 5288 (2013)
D.N. Pansare, N.A. Mulla, C.D. Pawar, V.R. Shende, D.B. Shinde, Bioorg. Med. Chem. Lett. 24, 3569 (2014)
N. Azgomi, M. Mokhtary, J. Mol. Catal. A: Chem. 398, 58 (2015)
L.D. Khillare, M.R. Bhosle, A.R. Deshmukh, R.A. Mane, Res. Chem. Intermed. 41, 8955 (2015)
J. Kolb, B. Beck, M. Almstetter, S. Heck, E. Herdtweck, A. Dömling, Mol. Divers. 6, 297 (2003)
S.A.F. Rostom, I.M. El-Ashmawy, H.A. Abd El Razik, M.H. Badr, H.M.A. Ashour, Bioorg. Med. Chem. 17, 882 (2009)
A.S. Shahvelayati, I. Yavari, A.S. Delbari, Chin. Chem. Lett. 25, 119 (2014)
V.P. Modi, P.N. Patel, H.S. Patel, Der Pharm. Lett. 4, 120 (2011)
J.R. Mali, U.R. Pratap, P.D. Netankar, R.A. Mane, Tetrahedron Lett. 50, 5025 (2009)
H.R. Zhao, H.Y. Wang, X.W. Meng, Acta Crystallogr. Sect. E: Struct. Rep. Online 66, o3285 (2010)
H.G. Hacker, P.W. Elsinghorst, S. Michels, J. Daniels, G. Schnakenburg, M. Gutschow, Synthesis 7, 1195 (2009)
APEX II v2012.2-0 Software User Guide, SAINT software user guide version 7.06a, SADABS version 2.01, Bruker Analytical X-ray Systems: Madison, WI, (2008)
G.M. Sheldrick, A short history of SHELX. Acta Crystallogr. Sect. A: Found. Crystallogr. 64, 112 (2008)
Copies of the data can be obtained free of charge on application to the Cambridge Crystallographic Data Centre (CCDC), 12 Union Road, Cambridge CB2 1EZ, U.K. (fax, (+44) 1223 336033; e-mail, deposit@ccdc.cam.ac.uk)
Acknowledgements
We gratefully acknowledge financial support from the Research Council of the University of Sistan and Baluchestan. Also, we wish to express our gratitude to Dr. Majid. Kolahdoozan for his helpful discussions.
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Hossaini, M., Heydari, R., Maghsoodlou, M.T. et al. Novel (4-oxothiazolidine-2-ylidene)benzamide derivatives: synthesis, characterization and crystal structures. Res Chem Intermed 43, 4189–4199 (2017). https://doi.org/10.1007/s11164-017-2872-0
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s11164-017-2872-0