Chlorination/cyclodehydration of amino alcohols with SOCl2: an old reaction revisited

J Org Chem. 2008 Jan 4;73(1):312-5. doi: 10.1021/jo701877h. Epub 2007 Dec 5.

Abstract

A simple, one-pot preparation of cyclic amines via efficient chlorination of amino alcohols with use of SOCl(2) has been developed. This approach obviates the need for the classical N-protection/O-activation/cyclization/deprotection sequence commonly employed for this type of transformation. The reaction pathways and the general scope of this method have also been investigated.

MeSH terms

  • Amino Alcohols / chemical synthesis*
  • Amino Alcohols / chemistry
  • Cyclization
  • Dehydration
  • Halogenation
  • Molecular Structure
  • Stereoisomerism
  • Sulfur Oxides / chemistry*

Substances

  • Amino Alcohols
  • Sulfur Oxides
  • thionyl chloride