An efficient tandem approach for the synthesis of functionalized 2-pyridone-3-carboxylic acids using three-component reaction in aqueous media

Abstract

Novel analogs of 2-pyridone-3-carboxylic acids 4a-l have been prepared by the three-component reaction of 3-formyl chromone, Meldrum's acid, and primary amines in the presence of a catalytic amount of diammonium hydrogen phosphate in water. Good-to-high yields, easy work-up, and an environmentally friendly profile are the advantages of this method for the synthesis of 2-pyridone-3-carboxylic acid derivatives.

Sequential multicomponent synthesis of highly functionalized pyridin-2(1H)-one derivatives

“…Most relevant to the work presented here are its reaction with malonodiamide to afford pyridin‐2(1 H )‐one derivatives, and its reaction with acetoacetone and ammonium acetate to form pyridine rings . Its reaction with dialkyl malonates and amines also allowed the synthesis of 3‐substituted pyridin‐2(1 H )‐ones …”

A one-pot three-component reaction involving 2-aminochromone in aqueous micellar medium: a green synthesis of hexahydrochromeno[2,3- $$b$$ b ]quinolinedione

“…3) [49], whereas the use of 3-aminocoumarin as the amine-component produced E (Scheme 1, eq. 4) [50].…”

Efficient synthesis of chromonylpyrano[c]coumarin, chromonylbenzo[b]pyran, and pyrano[d]pyrimidine in aqueous media

“…Carrying out multicomponent reactions (MCRs) for the coupling of two biologically active heterocyclic skeletons in aqueous media is an interesting subject in green chemistry [33][34][35][36][37][38][39][40]. In continuation of our research work to design one-pot reactions based on 3-formyl chromone 1a [41][42][43], herein we report an approach for the synthesis of new functionalized heterocycles, i.e., chromonylpyrano[c]coumarin, chromonylbenzo[b]pyran, and pyrano[d]pyrimidine in aqueous media and in the presence of a catalytic amount of K 2 CO 3 via a three-component reaction of 3-formylchromone 1, malononitrile or alkyl cyanoacetate 2, and cyclic 1,3-diones such as dimedone and barbiturates 3, and 4-hydroxy coumarin or 4-hydroxy-6-methyl-2-pyrone 5. (Scheme 1).…”