Reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of bidentate nucleophiles

Mol Divers. 2007 Feb;11(1):1-5. doi: 10.1007/s11030-006-9052-2. Epub 2006 Nov 23.

Abstract

The reaction between alkyl isocyanides and isopropylidene Meldrum's acid in the presence of 1,2-ethanediol leads to N (1)-(alkyl)-2-(5,7-dioxo-1,4-dioxepane-6-yl)-2-methylpropanamides. 1,3-Propanediol or 1,4-butanediol produce hydroxyalkyl 1-(tert-butyl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxylates. When the reaction was performed in the presence of catechol, bis(2-hydroxyphenyl) 2-[2-(tert-butylamino)-1,1-dimethyl-2-oxoethyl]malonate was obtained. 2-Aminophenols react with alkyl isocyanides in the presence of isopropylidene Meldrum's acid to produce 1-alkyl-N (3)-(2-hydroxyaryl)-4,4-dimethyl-2,5-dioxo-3-pyrrolidinecarboxamides in good yields.

MeSH terms

  • Amides / chemical synthesis
  • Butylene Glycols / chemistry*
  • Catechols / chemistry*
  • Combinatorial Chemistry Techniques
  • Cyanides / chemistry*
  • Ethylene Glycol / chemistry
  • Glycols / chemistry*
  • Propylene Glycols / chemistry
  • Pyrrolidines / chemical synthesis

Substances

  • Amides
  • Butylene Glycols
  • Catechols
  • Cyanides
  • Glycols
  • Propylene Glycols
  • Pyrrolidines
  • 1,3-propanediol
  • 1,4-butanediol
  • Ethylene Glycol
  • catechol