Next Article in Journal
Evaluation of Flavonoid Contents and Antioxidant Capacity of the Aerial Parts of Common and Tartary Buckwheat Plants
Previous Article in Journal
Deoxycalyciphylline B, a Hepatotoxic Alkaloid from Daphniphyllum calycinum
Molecules 2012, 17(8), 9652-9667; doi:10.3390/molecules17089652
Article

Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity

1,†,*  and 2,†
1 Chemistry Department, Faculty of Science, Cairo University, Cairo 12613, Egypt 2 Chemistry Department, Faculty of Science, Suez Canal University, Ismailia 41522, Egypt Current address: Chemistry Department, Faculty of Science, Taif University, Taif 21974, Saudi Arabia.
* Author to whom correspondence should be addressed.
Received: 7 July 2012 / Revised: 3 August 2012 / Accepted: 7 August 2012 / Published: 13 August 2012
(This article belongs to the Section Organic Synthesis)
View Full-Text   |   Download PDF [275 KB, uploaded 18 June 2014]   |   Browse Figure

Abstract

Biginelli reaction of ethyl acetoacetate, thiourea and the appropriate aromatic aldehyde was used to produce ethyl 4-aryl-6-methyl-2-thioxo-1,2,3,4-tetrahydro-pyrimidine-5-carboxylates, that reacted with bromomalononitrile to give ethyl 3-amino-5-aryl-2-cyano-7-methyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates rather than the isomeric 7H-thiazolo[3,2-a]pyrimidines. Thiazolopyrimidine derivatives reacted with carbon disulphide to yield ethyl 9-aryl-7-methyl-2,4-dithioxo-2,3,4,9-tetrahydro-1H-thiazolo[3,2-a:4,5-d']dipyrimidine-8-carboxylates, that reacted with phenacyl bromide to produce ethyl 8-methyl-10-(4-methoxyphenyl)-3-substituted-5-thioxo-2(un)subatituted-10H-thiazolo[3'',2'':1',2']pyrimido[4',5':4,5]thiazolo[3,2-a]pyrimidine-9-carboxylates. The aforementioned reactions were carried out using both conventional chemical methods and with the assistance of microwave irradaition. Comparison between both methods showed that the microwave assisted method is preferable because of the time reduction and yield improvements achieved. The new compounds were tested for their biological activity as antioxidants, antibacterial or antifungal agents. Some of the new compounds were found to have moderate to good antioxidant and antimicrobial activities.
Keywords: biginelli reaction; 2-thioxopyrimidines; thiazolopyrimidines; thiazolo-dipyrimidines; thiazolopyrimidothiazolopyrimidines; antioxidant activity; antimicrobial activity biginelli reaction; 2-thioxopyrimidines; thiazolopyrimidines; thiazolo-dipyrimidines; thiazolopyrimidothiazolopyrimidines; antioxidant activity; antimicrobial activity
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Share & Cite This Article

Export to BibTeX |
EndNote


MDPI and ACS Style

Youssef, M.M.; Amin, M.A. Microwave Assisted Synthesis of Some New Thiazolopyrimidine, Thiazolodipyrimidine and Thiazolopyrimidothiazolopyrimidine Derivatives with Potential Antioxidant and Antimicrobial Activity. Molecules 2012, 17, 9652-9667.

View more citation formats

Related Articles

Article Metrics

Comments

Citing Articles

[Return to top]
Molecules EISSN 1420-3049 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert