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N-Substituted cyanacetohydrazides in the synthesis of 3,3-dialkyl-1,2,3,4-tetrahydroisoquinolines by Ritter reaction

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Chemistry of Heterocyclic Compounds Aims and scope

Cyanacetohydrazide, protected at the nitrogen atom of hydrazide group, underwent cyclocondensation by Ritter reaction with 3,3-dialkylbenzylcarbinols, forming 3,3-dialkyl-1,2,3,4-tetrahydroisoquinolines. The reagents used for the protection of hydrazide group were benzaldehyde, benzoyl chloride, phenyl isocyanate, and phenyl isothiocyanate. As a result, N-substituted derivatives of 2-(3,3-dialkyl-3,4-dihydroisoquinolin-1(2Н)-ylidene)acetohydrazide were obtained – N-phenylmethylidene ethanehydrazide, acetylbenzohydrazide, and N-phenylhydrazinecarboxamide. Cyanacetohydrazide that was acylated with phenyl isothiocyanate gave a heterocyclization product – 1,3,4-thiadiazole under these conditions.

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X-ray structural analysis was performed within the framework of State contract with the Federal Agency for Scientific Organizations of Russia (No. 0089-2014-0009).

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Authors and Affiliations

  1. Perm State Pharmaceutical Academy, 2 Polevaya St., Perm, 614990, Russia

    Alexander G. Mikhailovskii, Aleksey S. Yusov & Oksana V. Gashkova

  2. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Akademika Semenova St., Chernogolovka, 142432, Moscow oblast, Russia

    Denis V. Korchagin

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  1. Alexander G. Mikhailovskii
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  2. Denis V. Korchagin
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  3. Aleksey S. Yusov
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  4. Oksana V. Gashkova
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Correspondence to Alexander G. Mikhailovskii.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2017, 53(10), 1114–1119

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Mikhailovskii, A.G., Korchagin, D.V., Yusov, A.S. et al. N-Substituted cyanacetohydrazides in the synthesis of 3,3-dialkyl-1,2,3,4-tetrahydroisoquinolines by Ritter reaction. Chem Heterocycl Comp 53, 1114–1119 (2017). https://doi.org/10.1007/s10593-017-2180-z

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  • DOI: https://doi.org/10.1007/s10593-017-2180-z

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