Publication details

The Reactivity Study on N3, N3-(3-Oxapentan-1,5-diyl)-N1-(2-phenyl-3,4-dihydroquinazolin-4-ylidene)thioureas

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Authors

MOHAMED Walid Fathalla PAZDERA Pavel

Year of publication 2001
Type Article in Proceedings
Conference XXVth Conference of Organic Chemists
MU Faculty or unit

Faculty of Science

Citation
Field Organic chemistry
Keywords Quinazolines; Thioureas; Guanidines; Desulfurization
Description The model compound N3,N3-(3-oxapentan-1,5-diyl)-N1-(2-phenyl-3,4-dihydroquinazolin-4-ylidene) thiourea 1 was synthesized in a one-pot reaction from N1-(2-cyanophenyl) benzamide as reported. It was proved from the computational studies of 1 that the competing nucleophile sites would be the N3 of quinazoline skeleton and sulfur atom. It was found that the 1 undergoes transamination reactions with primary and secondary amines. The compound 1 gives the alkylation reaction at the sulfur atom. The later result was attributed to the hard-soft theory. The model compound 1 reacts with secondary amines in the presence of H2O2 to produce the guanidine derivative by the elimination of the sulfanyl group.
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