Next Article in Journal
Preparation of Quinolinium Salts Differing in the Length of the Alkyl Side Chain
Previous Article in Journal
Zinc Phthalocyanine Labelled Polyethylene Glycol: Preparation, Characterization, Interaction with Bovine Serum Albumin and Near Infrared Fluorescence Imaging in Vivo
Article Menu

Article Versions

Export Article

Open AccessArticle
Molecules 2012, 17(6), 6362-6385; doi:10.3390/molecules17066362

4-Thiazolidinones in Heterocyclic Synthesis: Synthesis of Novel Enaminones, Azolopyrimidines and 2-Arylimino-5-arylidene-4-thiazolidinones

1
Chemistry Department, Faculty of Science, Kuwait University, P.O. Box 5969, Safat 13060, Kuwait
2
Chemistry Department, Faculty of Science, Fayoum University, Fayoum 63514, A. R., Egypt
*
Author to whom correspondence should be addressed.
Received: 8 May 2012 / Revised: 18 May 2012 / Accepted: 22 May 2012 / Published: 25 May 2012
(This article belongs to the Section Organic Synthesis)
Download PDF [764 KB, uploaded 18 June 2014]   |  

Abstract

The 4-thiazolidinones 3a–d were used as a key intermediates for the synthesis of 2-arylimino-5-arylidene-4-thiazolidinones derivatives 7a–p via nucleophilic addition reactions with the arylidene malononitrile. Moreover the 4-thiazolidinones 3a and 3c condensed with the DMF-DMA to form the corresponding enamines 8 and 9 depending on the reaction conditions. Otherwise the 4-thiazolidinone 3b reacts regioselectively with DMF-DMA to afford the enaminones 10 and 11, respectively. The latter reacts with many heterocyclic amines affording polyfunctionally substituted fused pyrimidine derivatives 13–18. The enamine 8b was also reacted with the 3-amino-1,2,4-triazole to afford the acyclic product 19, which could not be further cyclized to the corresponding tricyclic system 20. Moreover the 4-thiazolidinone 3c reacted with the benzenediazonium chloride to afford the arylhydrazones 12. The X-ray single crystal technique was employed in this study for structure elucidation and Z/E potential isomerism configuration determination. The X-ray crystallographic analyses of eight products could be obtained, thus establishing with certainty the structures proposed in this work.
Keywords: 4-thiazolidinone; enaminones; arylidene malononitrile; dimethylformamide dimethylacetal; azolopyrimidine 4-thiazolidinone; enaminones; arylidene malononitrile; dimethylformamide dimethylacetal; azolopyrimidine
Figures

This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

MDPI and ACS Style

Behbehani, H.; Ibrahim, H.M. 4-Thiazolidinones in Heterocyclic Synthesis: Synthesis of Novel Enaminones, Azolopyrimidines and 2-Arylimino-5-arylidene-4-thiazolidinones. Molecules 2012, 17, 6362-6385.

Show more citation formats Show less citations formats

Related Articles

Article Metrics

Article Access Statistics

1

Comments

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