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SYNTHESIS OF HEXAHYDROPYRIDAZINE-3-ONES BY REACTIONS BETWEEN DONOR-ACCEPTOR CYCLOPROPANES AND PHENYLHYDRAZINE

Игорь Викторович Трушков, Чагаровский Алексей Олегович, Иванова Ольга Александровна, Шумский Алексей Николаевич
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Abstract


The nickel perchlorate-initiated reaction between dimethyl esters of 2-aryl- and 2-styryl-substituted cyclopropane-1,1-dicarboxylic acids and phenylhydrazine proceeded with opening of the cyclopropane ring and formation of a mixture containing acyclic and cyclic products: [2-(1-phenylhydrazinyl)alkyl]malonates and 1-phenylhexahydropyridazin-3-ones. Reaction conditions were found for preparative synthesis of polyfunctional hexahydropyridazin-3-ones. Unlike the other starting materials, 2-(p-methoxystyryl)-substituted cyclopropane reacted with the terminal NH2 group of phenylhydrazine, resulting in the formation of 1-(phenylamino)pyrrolidin-2-one.

 


Keywords


hexahydropyridazin-3-ones, donor-acceptor cyclopropanes, phenylhydrazine, nucleophilic ring opening.

Full Text: PDF (Russian) Supplementary File(s): Supporting information (1MB)


 

 

Latvian Institute of Organic Synthesis - Aizkraukles iela, 21, Riga, LV-1006, Latvia - hgs@osi.lv