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Synthesis and cyclization of 3-substituted 1-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)thioureas

P. Pazdera, M. Řezka, and E. Nováček

Department of Organic Chemistry, Faculty of Natural Sciences, J. E. Purkyně University, CS-61137 Brno

 

Abstract: New 3-substituted l-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)thioureas were prepared by the reaction of 2-isothiocyanato-3-cyano-4,5,6,7-tetrahydrobenzo[6]thiophene with primary amines (ethyl-, isopropyl-, tert-butyl-, cyclohexylamine, aniline, 4-nitroaniline, 4-anisidine, Phenylhydrazine, 4-hydrazinobenzonitrile, ethyl 4-hydrazinobenzoate, hy­drazine) in the mixture of dichloromethane and petroleum ether. Besides 3-amino-l-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)thiourea, 3-amino-4-imino-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]-l,2,3,4-tetrahydropyrimidine-2-thione as a product of cyclization was formed. 3-Substituted l-(3-cyano-4,5,6,7-tetrahydrobenzo[b]thien-2-yl)thioureas underwent in boiling ethylene glycol monomethyl ether the cyclization to 3-substituted 4-imino-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]-1,2,3,4-tetrahydropyrimidine-2-thiones. 3-Isopropyl, 3-tert-butyl, and 3-cyclohexyl derivatives did not react.

Full paper in Portable Document Format: 442a229.pdf

 

Chemical Papers 44 (2) 229–240 (1990)

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