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Report | Regular issue | Vol 22, No. 11, 1984, pp.2529-2540
Published online, 1st January, 1970
DOI: 10.3987/R-1984-11-2529
Reaction of Diphenylcyclopropenone with 2-Aminothiazoles and Related Compounds

Albert Kascheres,* Juan L. Reyes R., and Suzana M. Fonseca

*Instituto de Química, Universidade Estadual de Campinas (UNICAMP), Caixa Postal 6154, CEP 13083-970, Campinas, Sao Paulo, Brazil


Diphenylcyclopropenone (1) reacts readily with 2-aminothiazole (7a) in THF to produce cis-5,6-dihydro-5,6-diphenyl-7H-thiazolo[3,2-a]pyrimidin-7-one (8a) in high yield. 2-Amino-5-ethyl-1,3,4-thiadiazole (7b) and 2-aminothiazoline (7c) react similarly, while 2-amino-4-methylthiazole (7d) affords both 8d and the cis-2,3-diphenylacrylamide 11. 2-Amino-4-ethyl-5-methylthiazole (7e) and 2-aminobenzothiazole (7f) give no 8, the products isolated being the corresponding cis-2,3-diphenylacrylamides 12 and 13. 2-Aminobenzimidazole (16a) yields 17a and 17b, while 2-amino-5-chloro-benzimidazole (16b) produces 18a, 18b, and 19.