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Chemistry of Heterocyclic Compounds

, Volume 43, Issue 7, pp 900–905 | Cite as

Enamines of the 1,2,3,4-tetrahydroiso-quinoline series in the Chichibabin synthesis of pyrrolo[2,1-a]isoquinolines and in reaction with oxalyl chloride

  • N. N. Polygalova
  • A. G. Mikhailovskii
  • E. V. Vikhareva
  • M. I. Vakhrin
Article

Abstract

It has been shown that the Chichibabin reaction of enamines of the 1,2,3,4-tetrahydroisoquinoline series and 1,2,3,4-tetrahydrobenzo[f]isoquinoline series with p-bromophenacyl bromide leads to pyrrolo[2,1-a]isoquinoline derivatives. The same heterocyclic system is obtained on interaction of 1-alkyl-3,4-dihydroisoquinolines or their benzo[f]-analogs with oxalyl chloride. The obtained dioxopyrrolines form derivatives of benzo[g]quinoxalino[2,3-b]indolizine on condensation with o-phenylenediamine.

Keywords

1-alkyl-3,4-dihydroisoquinolines benzo[g]quinoxalino[2,3-b]indolizine derivatives p-bromophenacyl bromide enamines of the 1,2,3,4-isoquinoline series oxalyl chloride pyrrolo[2,1-a]isoquinolines 1,2,3,4-tetrahydrobenzo[f]isoquinolines Chichibabin reaction condensation with o-phenylenediamine 

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Copyright information

© Springer Science+Business Media, Inc. 2007

Authors and Affiliations

  • N. N. Polygalova
    • 1
  • A. G. Mikhailovskii
    • 1
  • E. V. Vikhareva
    • 1
  • M. I. Vakhrin
    • 1
  1. 1.Perm State Pharmaceutical AcademyPermRussia

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