Electrophilic ipso-iodocyclization of N-(4-methylphenyl)propiolamides: selective synthesis of 8-methyleneazaspiro[4,5]trienes

J Org Chem. 2008 May 2;73(9):3658-61. doi: 10.1021/jo800328a. Epub 2008 Apr 1.

Abstract

A novel and selective method for the synthesis of 8-methylenespiro[4,5]trienes via intramolecular electrophilic ipso-iodocyclization of N-(4-methylphenyl)propiolamides has been developed. In the presence of ICl or I 2, 8-methylene-1-azaspiro[4,5]trienes were selectively prepared from the electrophilic ipso-iodocyclization of N-(4-methylphenyl)propiolamides in moderate to good yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemical synthesis*
  • Amides / chemistry
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Cyclization
  • Electrons*
  • Iodine / chemistry*
  • Methylation
  • Molecular Structure
  • Spiro Compounds / chemical synthesis*
  • Spiro Compounds / chemistry

Substances

  • Amides
  • Aza Compounds
  • Spiro Compounds
  • Iodine