Simple, One-Pot, and Three-Component Coupling Reactions of Azaarenes (Phenanthridine, Isoquinoline, and Quinoline), with Acetylenic Esters Involving Methyl Propiolate or Ethyl Propiolate in the Presence of NH-Heterocyclic or 1,3-Dicarbonyl Compounds

Abstract

Three-component reactions involving azaarenes (quinoline, isoquinoline, and phenanthridine) with acetylenic esters such as methyl propiolate or ethyl propiolate in the presence of NH-heterocyclic compounds (carbazole, maleimide, 5-nitroindazole, 2-benzoxazolinone, indole, and 2-methylindole) or 1,3-dicarbonyl compounds involving acetylacetone and N,N′-dimethylbar bituric acid are described. The reactions proceeded smoothly at room temperature without a catalyst and with excellent yields. This method is very useful for functionalizing aza-aromatic compounds in a one-pot operation.

GRAPHICAL ABSTRACT

Keywords:

• Azaarenes
• 1,3-dicarbonyl compounds
• enamino esters
• ethyl propiolate
• methyl propiolate
• NH-heterocyclic compounds

ACKNOWLEDGMENT

We gratefully acknowledge financial support from the Research Council of the Chabahar Maritime University.