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Paper | Regular issue | Vol 32, No. 7, 1991, pp.1317-1325
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5736
Triethylamine, Ethanol — Mediated Disciplined Reactions of S-Benzylisothiouronium Chloride with Unsaturated 2-Oxazolin-5-ones: Synthesis of (Z)-2-Amino-4-arylmethylene-2-imidazolin-5-ones, 5-Benzoylamino-2-benzylthio-6-oxo-4,4-spirocyclohexyl-1,4,5,6-tetrahydropyrimidine, and Their Structure

Arya K. Mukerjee,* Kiran Joseph, Seyed-Saied Homami, and Ahmad M. Tikdari

*Department of Chemistry, Faculty of Science, Banaras Hindu University, Varanasi - 221005, India

Abstract

Triethylamine-mediated condensation of S-benzylisothiouronium chloride with (Z)-4-arylmethylene-2-phenyl-2-oxazolin-5-ones (4) in ethanol gives (Z)-2-amino-4-arylmethylene-2-imidazolin-5-ones (7), whereas the similar reaction with 4-cyclohexylidene-2-phenyl-2-oxazolin-5-ones (5) produces 5-benzoylamino-2-benzylthio-6-oxo-4,4-spirocyclohexyl-1,4,5,6-tetrahydropyrimidine (15) which on aminolyses with arylamines affords the corresponding 2-arylamino derivatives (16).