European Journal of Chemistry

Regioselective synthesis of new 2-(E)-cyano(oxazolidin-2-ylidene)thiazoles



Main Article Content

Mehdi Bakavoli
Hamid Beyzaei
Mohammad Rahimizadeh
Hossein Eshghi

Abstract

Reaction of 2-(oxazolidin-2-ylidene)malononitrile (1) with phosphorus pentasulfide gave the corresponding thioamide derivative (2a) in a regioselective manner. Reaction of this compound with several α-bromocarbonyl compounds gave new 2-(E)-cyano(oxazolidin-2-ylidene)thiazoles (3a-g). The chemical structures of novel compounds were confirmed by 1H NMR, elemental analysis, FT-IR spectrometry and mass spectrophotometric analyses.

2_3_356_358_800


icon graph This Abstract was viewed 1483 times | icon graph Article PDF downloaded 672 times

How to Cite
(1)
Bakavoli, M.; Beyzaei, H.; Rahimizadeh, M.; Eshghi, H. Regioselective Synthesis of New 2-(E)-cyano(oxazolidin-2-ylidene)thiazoles. Eur. J. Chem. 2011, 2, 356-358.

Article Details

Share
Crossref - Scopus - Google - European PMC
References

[1]. Masquelin, T.; Obrecht, D. Tetrahedron 2001, 6, 153-156.
http://dx.doi.org/10.1016/S0040-4020(00)01003-6

[2]. Hirai, K.; Sugimoto, H.; Ishiba, T. J. Org. Chem. 1980, 45, 253-260.
http://dx.doi.org/10.1021/jo01290a010

[3]. Walczynski, K.; Zuiderveld, O. P.; Timmerman, H. Eur. J. Med. Chem. 2005, 40, 15-23.
http://dx.doi.org/10.1016/j.ejmech.2004.09.010
PMid:15642406

[4]. Andreani, A.; Rambaldi, M.; Leoni, A.; Locatelli, A.; Andreani, F.; Gehret, J. C. Pharm. Acta Helv. 1996, 71, 247-252.
http://dx.doi.org/10.1016/S0031-6865(96)00021-0

[5]. Ali, T. E.; ElâKazak, A. M. Eur. J. Chem 2010, 1, 6-11.
http://dx.doi.org/10.5155/eurjchem.1.1.6-11.12

[6]. Andreani, A.; Burnelli, S.; Granaiola, M.; Leoni, A.; Locatelli, A.; Morigi, R.; Rambaldi, M.; Varoli, L.; Calonghi, N.; Cappadone, C.; Farruggia, G.; Zini, M.; Stefanelli, C.; Masotti, L.; Radin, N. S.; Shoemaker, R. H. J. Med. Chem. 2008, 51, 809-816.
http://dx.doi.org/10.1021/jm701246g
PMid:18251494

[7]. Budriesi, R.; Ioan, P.; Locatelli, A.; Cosconati, S.; Leoni, A.; Ugenti, M. P.; Andreani, A.; Di Toro, R.; Bedini, A.; Spampinato, S.; Marinelli, L.; Novellino, E.;Chiarini, A. J. Med. Chem. 2008, 51, 1592-1600.
http://dx.doi.org/10.1021/jm070681+
PMid:18303827

[8]. Anandan, S. K.; Ward, J. S.; Brokx, R. D.; Denny, T.; Bray, M. R.; Patel, D. V.; Xiao, X. Y. Bioorg. Med. Chem. Lett. 2007, 17, 5995-5999.
http://dx.doi.org/10.1016/j.bmcl.2007.07.050

[9]. Potewar, T. M.; Ingale, S. A.; Srinivasan, K. V. Tetrahedron 2007, 63, 11066-11069.
http://dx.doi.org/10.1016/j.tet.2007.08.036

[10]. Zambon, A.; Borsato, G.; Brussolo, S.; Frascella, P.; Lucchini, V. Tetrahedron Lett. 2008, 49, 66-69.
http://dx.doi.org/10.1016/j.tetlet.2007.11.029

[11]. Franklin, P. X.; Pillai, A. D.; Rathod, P. D.; Yerande, S.; Nivsarkar, M.; Padh, H.; Vasu, K. K.; Sudarsanam, V. Eur. J. Med. Chem. 2008, 43, 129-134.
http://dx.doi.org/10.1016/j.ejmech.2007.02.008
PMid:17467123

[12]. Karegoudar, P.; Karthikeyan, M. S.; Prasad, D. J.; Mahalinga, M.; Holla, B. S.; Kumari, N. S. Eur. J. Med. Chem. 2008, 43, 261-267.
http://dx.doi.org/10.1016/j.ejmech.2007.03.014
PMid:17540482

[13]. Ochiai, M.; Nishi, Y.; Hashimoto, S.; Tsuchimoto, Y.; Chen, D. W. J. Org. Chem. 2003, 68, 7887-7888.
http://dx.doi.org/10.1021/jo020759o
PMid:14510572

[14]. Abdel-Rahman, R. M.; Tawfik Makki, M. S.; Ali, T. E.; Ibrahim, M. A. Eur. J. Chem. 2010, 1, 236-245.
http://dx.doi.org/10.5155/eurjchem.1.3.236-245.54

[15]. Bakavoli, M.; Beyzaei, H.; Rahimizadeh, M.; Eshghi, H.; Takjoo, R. Molecules 2009, 14, 4849-4857.
http://dx.doi.org/10.3390/molecules14114849
PMid:20032863

[16]. Chanu, E. G.; Singh, O. M.; Jang, S. H.; Lee, S.-G. Bull. Korean Chem. Soc. 2010, 31, 859-862.
http://dx.doi.org/10.5012/bkcs.2010.31.04.859

[17]. Kaboudin, B.; Elhamifar, D. Synthesis 2006, 2, 224-226.
http://dx.doi.org/10.1055/s-2005-918507

Supporting Agencies

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).