Chemistry of Heterocyclic Compounds

, Volume 14, Issue 2, pp 157–172 | Cite as

Fischer synthesis of indoles from 2,6-disubstituted arylhydrazones

  • R. Fusco
  • F. Sannicoló
Article

Abstract

A review of the literature data on the Fischer synthesis of indoles from 2,6-disubstituted arylhydrazones is given. As a result of their own experimental studies of the indolization of hydrazones from 8-R-N-amino-1,2,3,4-tetrahydroquinolines the authors established that no less than five different transformations of the cyclohexadienoneimine intermediate, including 1,2 and 1,4 shifts and splitting out of the substituent, may follow attack on the 8 position of the tetrahydroquinoline ring. Attack in the 10 position of the tetrahydroquinoline ring leads to another cyclohexadienoneimine, which undergoes indolization with the loss of apropylamine chain via a different mechanism. It was proved by experiments with labeled compounds that 1,3 migration of the methyl group (R=CH3) is the result of a double 1,2 shift, while the 1,4 shift is a direct reaction.

Keywords

Methyl Migration Experimental Study Organic Chemistry Indole 

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Copyright information

© Plenum Publishing Corporation 1978

Authors and Affiliations

  • R. Fusco
    • 1
  • F. Sannicoló
    • 1
  1. 1.Institute of Industrial ChemistryCenter for the Study of Methods for the Synthesis and Stereochemistry of Special Organic SystemsMilanItaly

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