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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… Click to show full abstract
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.
Journal Title: Chemistry of Heterocyclic Compounds
Year Published: 2017
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