Catalyst-Free One-Pot Three-Component Synthesis of Diversely Substituted 5-Aryl-2-oxo-/thioxo-2,3-dihydro-1 H-benzo[6,7]chromeno[2,3- d]pyrimidine-4,6,11(5 H)-triones Under Ambient Conditions

Goutam Brahmachari; Nayana Nayek

doi:10.1021/acsomega.7b00791

Catalyst-Free One-Pot Three-Component Synthesis of Diversely Substituted 5-Aryl-2-oxo-/thioxo-2,3-dihydro-1 H-benzo[6,7]chromeno[2,3- d]pyrimidine-4,6,11(5 H)-triones Under Ambient Conditions

ACS Omega. 2017 Aug 28;2(8):5025-5035. doi: 10.1021/acsomega.7b00791. eCollection 2017 Aug 31.

Authors

Goutam Brahmachari¹, Nayana Nayek¹

Affiliation

¹ Laboratory of Natural Products & Organic Synthesis, Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731 235, West Bengal, India.

Abstract

A simple, catalyst-free, straightforward, and highly efficient one-pot synthesis of pharmaceutically interesting diverse kind of a new series of functionalized 5-aryl-2-oxo-/thioxo-2,3-dihydro-1H-benzo[6,7]chromeno[2,3-d]pyrimidine-4,6,11(5H)-triones 4 (4-1-4-37) and substituted 5,5'-(1,4-phenylene)bis(2-oxo-/thioxo-2,3-dihydro-1H-benzo[6,7]chromeno[2,3-d]pyrimidine-4,6,11(5H)-trione) derivatives 4' (4'-1-4'-3) has been developed based on a three-component reaction between barbituric acid/N,N-dimethylbarbituric acid/2-thiobarbituric acid (1), aromatic aldehydes (2), and 2-hydroxy-1,4-naphthoquinone (3) in aqueous ethanol at room temperature (25-30 °C). The salient features of this protocol are mild reaction conditions, use of no catalyst, no need of column chromatographic purification, excellent yields, high atom economy, eco-friendliness, easy isolation of products, and reusability of reaction media.