Three-Component Synthesis of Functionalized 1-Azabuta-1,3-dienes from Alkyl Isocyanides, Activated Acetylenes, and Pyridin-2(1H)-one or Isoquinolin-1(2H)-one

Abstract

The 1:1 reactive intermediates generated by the addition of alkyl isocyanides to dialkyl acetylenedicarboxylates were trapped by pyridin-2(1H)-one and isoquinolin-1(2H)-one to yield highly functionalized 1-azabuta-1,3-dienes and, in some cases, minor amounts of ketenimines.

Keywords:

• Acetylenic esters
• alkyl isocyanides
• 1-azadienes
• ketenimines
• multicomponent reaction
• NH acids