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Russian Journal of Organic Chemistry

, Volume 55, Issue 5, pp 633–639 | Cite as

Synthesis and Acylation for Enaminoketohydrazides Derived from 2,2-Dialkyl-2,3-dihydrobenzo[f]isoquinolines

  • A. G. MikhailovskiiEmail author
  • D. A. Peretyagin
  • M. V. Dmitriev
Article

Abstract

The reaction of 6,6-dialkyl-5,6-dihydrobenzo[f]pyrrolo[2,1-a]isoquinoline-8,9-diones with hydrazine is used to prepare enaminoketohydrazides of the 2,2-dialkyl-2,3-dihydrobenzo[f]isoquinoline series, which are polyfunctional reagents. The acylation of the synthesized hydrazides with two equivalents of acylating reagents, such as benzoyl chloride, phenyl isocyanate, phenyl isothiocyanate, and allyl isothiocyanate, involves exclusively the terminal NH2 group of the hydrazide fragment. The acylation with two equivalents of acetyl chloride leads to the substitution of both hydrogen atoms at the terminal NH2 group; the structure of the resulting N,N-diacyl derivative is proved by X-ray diffraction analysis.

Keywords

2,2-dialkyl-2,3-dihydrobenzo[f]isoquinoline enaminoketohydrazides acylation, terminal NH2 acylation benzoyl chloride isocyanates isothiocyanates N,N-diacyl derivative. 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. G. Mikhailovskii
    • 1
    Email author
  • D. A. Peretyagin
    • 1
  • M. V. Dmitriev
    • 2
  1. 1.Perm State Pharmaceutical AcademyPermRussia
  2. 2.Perm State National Research UniversityPermRussia

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