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■ Ring Closure Reactions of Adducts of Methacryloyl Isocyanate to Arylhydrazines and Their Related Componds

Otohiko Tsuge,* Taizo Hatta, and Ryuzo Mizuguchi

*Graduate Course of Applied Chemistry, Faculty of Engineering, Kumamoto Institute of Technology, 4-22-1, Ikeda, Kumamoto 860, Japan

Abstract

Methacryloyl isocyanate (MAI) reacted with arylhydrazines (1) to give semicarbazides (2) in good yields. Treatment of 2 with aqueous potassium hydroxide gave the corresponding 1-aryl-3-hydroxy-1,2,4-triazoles (3), whereas thermal ring closure of 2 afforded isomeric 2,3-dihydro-2-aryl-1,2,4-triazole-3(1H)-ones (4). MAI reacted with benzamidine to give directly 1,3,5-triazine-2(1H)-one (10) by the loss of water. On the other hand, the reaction of MAI with 1,3-diphenylguanidine afforded the 1:1 adduct (11), which on thermal decomposition gave the perhydropyrimidin-6(1H)-one (12) and perhydro-1,3,5-triazine-2,6-dione (13). The pathways for the formation of 4, 12 and 13 are also described.