Synthesis of substituted pyridines from 1,2-nucleophilic addition products of functionalized N-acyl-2,3-dihydropyridones

GÜZEL M., Watts J., Mcgilvary M., Wright M., Kiren S.

Tetrahedron Letters, vol.56, no.38, pp.5275-5277, 2015 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 56 Issue: 38
  • Publication Date: 2015
  • Doi Number: 10.1016/j.tetlet.2015.07.045
  • Journal Name: Tetrahedron Letters
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5275-5277
  • Keywords: Substituted pyridines, N-Acyl-2,3-dihydropyridones, Oxidative aromatization, Chloranil, 1,2-Nucleophilic addition
  • Istanbul Medipol University Affiliated: Yes

Abstract

Abstract We describe herein a general and efficient synthetic approach toward substituted pyridines from functionalized N-acyl-2,3-dihydropyridones in two steps; 1,2-addition with organocerium reagents and subsequent oxidative aromatization with chloranil. This strategy allows the generation of pyridines with various substitution patterns and introduces a variety of substituents including aryl, alkyl, alkynyl, alkenyl, and heteroaryl groups at the desired positions.