Isocyanide addition to pyridinium salts. Efficient entry into substituted nicotinonitrile derivatives

Org Lett. 2006 Dec 7;8(25):5789-92. doi: 10.1021/ol062327w.

Abstract

The addition of isocyanides to pyridinium salts is studied. The process takes place efficiently when a carboxamido group is present in the 3 position of the pyridine ring. The outcome of the reaction involves the stabilization of the nitrilium intermediate by the amide, which suffers a mild dehydration, leading regioselectively to beta-cyano-gamma-carbamoyl-1,4-dihydropyridines. In this way, a variety of nicotinamide derivatives were carbamoylated. Extension to quinolinium, isoquinolinium, and N-acylpyridinium salts is also reported. [reaction: see text]

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amides / chemistry
  • Cyanides / chemistry*
  • Niacinamide / chemistry
  • Nicotinic Acids / chemical synthesis*
  • Nitriles / chemical synthesis*
  • Pyridinium Compounds / chemical synthesis*
  • Quinolinium Compounds / chemical synthesis
  • Stereoisomerism

Substances

  • Amides
  • Cyanides
  • Nicotinic Acids
  • Nitriles
  • Pyridinium Compounds
  • Quinolinium Compounds
  • Niacinamide