ChemInform Abstract: Synthesis of New Thiazolidine and Imidazolidine Derivatives of Pharmacological Interest

Autor: Khaled F. Saied, Nadia K. El‐Aasar
Rok vydání: 2008
Předmět:
Zdroj: ChemInform. 39
ISSN: 1522-2667
0931-7597
DOI: 10.1002/chin.200836129
Popis: The hitherto unknown 5-(2-aryl-2-oxoethyl)-4-oxo-1,3-thiazolidines 1a-l have been synthesized viacycloaddition process between thiourea and/or its derivatives with 3-aroylpropenoic acids. 1H 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-thiazolines2a-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 isomers4a-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-cand 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.
Databáze: OpenAIRE
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