A Simple One‐Pot Synthesis of Fully Substituted 1H‐Pyridone[1,2‐a]‐Fused‐1,3‐Diazaheterocycles

Abstract

An efficient procedure for the synthesis of 7‐(aryl)‐8‐nitro‐2,3,6,7‐tetrahydroimidazo[1,2‐a]pyridinones, 8‐(aryl)‐9‐nitro‐3,4,7,8‐tetrahydropyridone[1,2‐a]pyrimidines and 9‐(aryl)‐10‐nitro‐2,3,4,5,8,9‐hexahydropyridone[1,2‐a]diazepine via one‐pot three component reaction of diamine, nitroketene dithioacetal (1,1‐bis(methylsulfanyl)‐2‐nitroethene), and coumarine‐3‐ carboxylic acid derivatives in EtOH under reflux conditions is reported. The advantages of this procedure are simplicity, easy purification, good yields, and catalyst‐free conditions. All products were confirmed by 1H‐ and 13C‐NMR, IR, MS, and X‐ray crystal structure analyses.

Synthesis of some new Aryl-azo derivatives clubbed with Pyridone and evaluating their Biological Broadcast.

“…Meanwhile, Pyridone analogues have pharmaceutical and an extensive assortment of pharmacological efficacies [9]. They display antibacterial [10], antifungal [11], anti-HIV [12], anticancer activities [13]. Pyridones act through many mechanisms including inhibition of tyrosine kinases such as FGFR and VEGFR, Met and TAM family kinases [14].…”

Synthesis of fused hydroxy dihydropyrroles and unexpected dihydropyrazine and dihydroquinoxaline derivatives based on heterocyclic ketene aminals

“…[18] A structure of ring fused with quinoxalines displays diverse pharmacological activities and has found applications in dyes, electron luminescent materials, and chemically controllable switches, as building blocks for the synthesis of anion receptors, cavitands, dehydroannulenes, and organic semiconductors, and as electrontransport materials in multilayer OLEDs. [25][26][27][28][29][30][31][32][33][34][35] Recently, Chen et al have reported a threecomponent domino reaction of HKAs with arylglyoxal monohydrates and β-diketone (like cyclohexane-1,3diones and 1,3-diphenylpropane-1,3-dione) for the synthesis of fused pyrroles. [20][21][22][23] To date, many works focus on the development of novel, MCRs, for constructing diverse and highly substituted fused heterocycles from available synthons heterocyclic ketene aminals (HKAs) with advantage for synthetic chemistry.…”

“…[24] HKAs have been used as bisnucleophiles to build fused heterocycles, because both the α-carbon and the secondary amino group can react with electrophiles. [25][26][27][28][29][30][31][32][33][34][35] Recently, Chen et al have reported a threecomponent domino reaction of HKAs with arylglyoxal monohydrates and β-diketone (like cyclohexane-1,3diones and 1,3-diphenylpropane-1,3-dione) for the synthesis of fused pyrroles. [36][37][38] To investigate the scope and limitations of this method and expand the diversity of the fused pyrrole library, another β-dicarbonyl compounds were used in this domino reaction.…”