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.
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Acknowledgment
This work received financial support from the Russian Science Foundation (grant 14-13-01178, study of arylsubstituted cyclopropane 1,1-diester reactions) and the Ministry of Education and Science of the Russian Federation (contract 02.а03.21.0008, study of styrylsubstituted cyclopropane 1,1-diesters).
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(11), 1220–1227
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Chagarovskiy, A.O., Ivanova, O.А., Shumsky, A.N. et al. Synthesis of hexahydropyridazin-3-ones by reactions between donor-acceptor cyclopropanes and phenylhydrazine. Chem Heterocycl Comp 53, 1220–1227 (2017). https://doi.org/10.1007/s10593-018-2203-4
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DOI: https://doi.org/10.1007/s10593-018-2203-4