European Journal of Chemistry

Synthesis of some new S-glycosyl pyrimidine and condensed pyrimidine derivatives

Article Sidebar

PDF
Published: Jun 30, 2012
DOI: https://doi.org/10.5155/eurjchem.3.2.241-246.597
Keywords:
S-glycosyl, Thienopyrimidine, S-alkyl pyrimidine, Pyrimidopyrimidine, Mercaptopyrimidine, Tetrazolopyrimindine derivatives
Section
Research Article
Issue
Vol. 3 No. 2 (2012): June 2012
Dates
Received 2012-02-10
Accepted 2012-03-02
Published 2012-06-30


Main Article Content

Wesam Saber Shehab
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt
Enaiat Kamel Mohamed
Department of Chemistry, Faculty of Science, Zagazig University, Zagazig, 44511, Egypt

Abstract

Mercaptopyrimidine (4) was synthesized by the reaction of isothiocyanate and acrylate (1). It was allowed to react with preacetylated sugar bromide and/or halomethylene derivatives to produce alkylated pyrimidines (5,7a-d). Hydrolysis of compound (5) produced compound (6). Interacyclization of compounds (7a-d) afforded thienopyrimidines (8a-d). Moreover oxidation of compound (7b) gave the corresponding thienopyrimidine dioxide (9). Cyanoethylation of compound (4) afforded compound (10) that reacted with hydrazine hydrate to give pyrazolopyrimidine (11). Oxidation of compound 4 afforded bisulphide (12). The cycloaddition product (13) was obtained by reaction of compound 4 with maleic anhydride. Pyrimidopyrimidine, pyrimidopyridazine and tetrazolopyriminde derivatives (16-20) were obtained by reaction of 4-chloropyrimidine (15) with thiourea, benzilhydrazone and sodium azide, respectively. N-alkylated pyrazolopyrimidine (21) was obtained by reaction of compound (15) with acetophenonehydrazone.

3_2_241_246_800


icon graph This Abstract was viewed 1194 times | icon graph Article PDF downloaded 699 times

How to Cite
(1)
Shehab, W. S.; Mohamed, E. K. Synthesis of Some New S-Glycosyl Pyrimidine and Condensed Pyrimidine Derivatives. Eur. J. Chem. 2012, 3, 241-246.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Padmaja, A.; Payani, T.; Diunneswra Reddy, G.; Padmavahi, V. Eur. J. Med. Chem. 2009, 44, 4557-4566.
http://dx.doi.org/10.1016/j.ejmech.2009.06.024
PMid:19631423

[2]. Sondhi, S. M.; Singh, N.; Johar, M.; Kumar, B. Bioorg. Med. Chem. 2005, 13, 6158-6166.
http://dx.doi.org/10.1016/j.bmc.2005.06.063

[3]. Sondhi, S. M.; Jain, S.; Dinodia, M.; Shukla, R.; Raghubir, R. Bioorg. Med. Chem. 2007, 15, 3334-3344.
http://dx.doi.org/10.1016/j.bmc.2007.03.028

[4]. Gary, R.; Gupta, S. P.; Gao, H.; Babu, M. S.; Debnath, A. K.; Hansch, C. Chem. Rev. 1999, 99, 3525-3601.
http://dx.doi.org/10.1021/cr9703358
PMid:11849030

[5]. Amr, A. E.; Mohamed, A. M.; Mohamed, S. F.; Abdel-Hafez, N. A.; Hamman, A. G. Bioorg. Med. Chem. 2006, 14, 5481-5488.
http://dx.doi.org/10.1016/j.bmc.2006.04.045

[6]. Ghorab, M. M.; Regab, F. A.; Alqasoumi, S. I.; Alafeefy, A. M.; Aboulmagd, S. A. Eur. J. Med. Chem. 2010, 45, 171-178.
http://dx.doi.org/10.1016/j.ejmech.2009.09.039
PMid:19853327

[7]. Breoutt, G. A.; Pease, J. E.; PCT. Int. Appl. Wo 2000012485. Chem. Abstr. 2000, 132, 194385.

[8]. Zhikareva, G. P.; Mostafanova, L. I.; Evstratova, M. I.; Polukhina, I. M.; Pushkina, T. V.; Pershin, G. N.; Yakhantov, L. N.; Khim. -Farm. Zh. 1982, 16, 183-185.

[9]. Assy, M. G.; Ouf, N. H.; Fikry, R. M. Polish J. Chem. 1995, 69, 892-895.

[10]. Assy, M. G.; Hassamine, G. A. Phosphorus sulfur 1995, 102, 95-102.

[11]. Assy, M. G. Sulfur Lett. 1990, 11, 75-80.

[12]. Drobinca, K.; Augustin, J.; Patai, S. 22 Edn., Wiley and Sons; New York 1977.

[13]. El-Dean, A. M. K.; Abdel-Moneam, M. E. J. Chinese Chem. Soc. 2002, 49, 1057-1060.

[14]. El-Dean, A. M. K.; Abdel-Moneam, M. E. Phosphorus sulfur 2002, 177, 2745-2751.

[15]. El-Bahaie, S.; Assy, M. G.; Ibrahim, Y. A. Sulfur Lett. 1989, 9, 201-208.

[16]. Cumha, S.; Bastos, R. M.; Silva, P. De O.; Nobre, C.; Giselle, A.; Vencato, I.; Lariucci, G.; Napolitano, H. B.; deOiveria, C. A.; Kato, L.; daSilva, C. C. Moatsh. Furchem. 2007, 138, 111-119.

[17]. Assy, M. G.; El-Bahaie, S.; Ibrahim, M. R.; Ibrahim, Y. A. Indian J. Chem. Soc. B 1996, 35(6), 598-601.

[18]. Amisworth, G.; Yanes, R. G. J. Am. Chem. Soc. 1953, 75, 4915-4922.
http://dx.doi.org/10.1021/ja01116a011

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).