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Synthesis of hexahydropyridazin-3-ones by reactions between donor-acceptor cyclopropanes and phenylhydrazine

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Chemistry of Heterocyclic Compounds Aims and scope

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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Authors and Affiliations

  1. National Research Center of Pediatric Hematology, Oncology and Immunology named after Dmitry Rogachev, 1 Samory Mashela St., Moscow, 117997, Russia

    Alexey O. Chagarovskiy, Olga А. Ivanova & Igor V. Trushkov

  2. RUDN University, 6 Miklukho-Maklaya St., Moscow, 117198, Russia

    Alexey O. Chagarovskiy & Igor V. Trushkov

  3. Lomonosov Moscow State University, Leninskiye Gory 1-3, Moscow, 119991, Russia

    Olga А. Ivanova

  4. N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, 4 Kosygina St., Moscow, 119334, Russia

    Alexey N. Shumsky

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  1. Alexey O. Chagarovskiy
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  2. Olga А. Ivanova
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  3. Alexey N. Shumsky
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  4. Igor V. Trushkov
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Corresponding authors

Correspondence to Olga А. Ivanova or Igor V. Trushkov.

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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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