Facile construction of novel heterocyclic compounds: three-component, one-pot synthesis of 2-hydroxybenzoyl-1,2-dihydropyridine-3-carboxylates, ketones, pyridone-3-carboxylates and benzopyrido-1,3-oxazole-4-carboxylates?

RSC Advances Pub Date: 2015-08-24 DOI: 10.1039/C5RA10185A

Abstract

A facile method has been developed for the preparation of novel heterocyclic compounds by the reaction of 3-formylchromones, benzylamines, and 2-aminophenols with 3-oxobutanoates. 3-Oxobutanoates bearing trifluoro or trichloro substituents and trifluoro containing 1,3-diketones facilitated the reaction. The reaction proceeds via a Schiff base mediated Michael addition followed by the selective addition of enamine to the carbonyl group adjacent to the trihalo group due to a strong electron withdrawing effect. The present three-component, one-pot protocol provided heterocyclic compounds without a catalyst.

Graphical abstract: Facile construction of novel heterocyclic compounds: three-component, one-pot synthesis of 2-hydroxybenzoyl-1,2-dihydropyridine-3-carboxylates, ketones, pyridone-3-carboxylates and benzopyrido-1,3-oxazole-4-carboxylates
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