ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7

Published monthly

Simple One-Step Syntheses of Heterocyclic Systems from (4Z)-2-Phenyl-4-(thien-2-ylmethylene)-1,3(4H)-oxazol-5-one

H. M. F. Madkour

Department of Chemistry, Faculty of Science, Ain Shams University, Abbasiya, Cairo, Egypt



Received: 26 November 2001

Abstract: The title compound (Ia) was synthesized and its (Z)-configuration was assigned. The present investigation was intended to study the behaviour of Ia towards nitrogen, carbon, and oxygen nucleophiles. Thus, reaction of Ia with p-toluidine in ethanol or in acetic acid afforded the thienylaminomethylidene-(4H)-oxazol-5-one and alkenamide without oxazolone ring together with the imidazolinone, respectively. Hydrazinolysis and azidolysis of Ia resulted in the vinylthiophene and tetrazole derivatives. The triazine and oxadiazinone were obtained upon the effect of phenylhydrazine and hydroxylamine on Ia, respectively.When compound Ia was allowed to react with carbon nucleophiles, namely phenylmagnesium bromide or dry benzene under Friedel—Crafts conditions, it gave the acylated product benzoylaminovinylthiophene whereas the ester thienylpropenoate was obtained from the reaction of Ia with sodium ethoxide. In the absence of aromatic hydrocarbon and in tetrachloroethane as inert solvent containing anhydrous AlCl3, Ia underwent intramolecular alkylation and/or acylation to afford the respective thieno[3,2-c]pyridine and cyclopentadieno[b]thiophene respectively.

Full paper in Portable Document Format: 565a313.pdf


Chemical Papers 56 (5) 313–319 (2002)

Monday, May 20, 2024

SCImago Journal Rank 2021
European Symposium on Analytical Spectrometry ESAS 2022
© 2024 Chemical Papers