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Synthesis of new thiazolidine and imidazolidine derivatives of pharmacological interest
Author(s) -
ElAasar Nadia K.,
Saied Khaled F.
Publication year - 2008
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570450302
Subject(s) - chemistry , thiazolidine , thiourea , thiazoline , imidazolidine , acetic acid , aryl , halogenation , medicinal chemistry , proton nmr , cycloaddition , stereochemistry , organic chemistry , catalysis , alkyl
The hitherto unknown 5‐(2‐aryl‐2‐oxoethyl)‐4‐oxo‐1,3‐thiazolidines 1a‐l have been synthesized via cycloaddition process between thiourea and/or its derivatives with 3‐aroylpropenoic acids. 1 H NMR spectra revealed the presence of 1a‐c as a tautmeric mixture. The presence of the thiazoline tautmers (1a‐c) ′ was confirmed by methylating the tautmeric mixture, to the respective methylated derivatives 2‐ N ‐methylanilino‐5‐(2‐aryl‐2‐oxoethyl)‐4‐oxo‐1,3‐thiazolines 2a‐c and 1g‐i . Acidic treatment of 1 provided the respective 2‐oxo homologues 3a‐i . When 1a‐d , k were refluxed with DMF, molecular rearrangement was achieved, providing the 4‐oxo‐2‐thioxoimidazolidine isomers 4a‐d , k . Bromination of 4a and 4d in hot acetic acid afforded the respective ( E,Z )‐5‐benzoylmethylene derivatives 5a,d which were prepared authentically. Thiation of 1a‐c and 4a‐c gave 5‐aryl‐2,3‐dihydro‐2‐phenyliminothieno[2,3‐ d ]thiazoles 6a‐c and 1‐phenyl‐5‐aryl‐2,3‐dihydro‐2‐thioxothieno[2,3‐ d ]imidazoles 7a‐c , respectively. The proposed structures have been confirmed by elemental analysis and spectroscopic data. The selected products showed different antimicrobial effect.