<i>N</i>-SUBSTITUTED CYANACETOHYDRAZIDES IN THE SYNTHESIS OF 3,3-DIALKYL-1,2,3,4-TETRAHYDROISOQUINOLINES BY RITTER REACTION

Authors

  • Александр Георгиевич Михайловский The Perm State Pharmaceutical Academy
  • Денис Владимирович Корчагин Институт проблем химической физики РАН,
  • Алексей Владимирович Юсов Пермская гос. фарм. акад.
  • Оксана Владиславовна Гашкова Пермская гос. фарм. акад.

DOI:

https://doi.org/10.1007/4002

Keywords:

cyanacetohydrazide, 2-(3, 3-dialkyl-3, 4-dihydroisoquinolin-1(2Н)-ylidene)acetohydrazide, 1, 3, 4-thiadiazole, heterocycli-zation, Ritter cyclization.

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.

 

Author Biographies

Александр Георгиевич Михайловский, The Perm State Pharmaceutical Academy

The chief of department for general chemistry, professor

Денис Владимирович Корчагин, Институт проблем химической физики РАН,

старший научный сотрудник

Алексей Владимирович Юсов, Пермская гос. фарм. акад.

аспирант кафедры

Оксана Владиславовна Гашкова, Пермская гос. фарм. акад.

старший преподаватель

Published

2017-11-27

Issue

Section

Original Papers