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环境条件下无催化剂一锅法三组分合成多样取代的5-芳基-2-氧代-/硫代-2,3-二氢-1-苯并[6,7]色烯并[2,3-]嘧啶-4,6,11(5)-三酮

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

作者信息

Brahmachari Goutam, Nayek Nayana

机构信息

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

出版信息

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

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-1-benzo[6,7]chromeno[2,3-]pyrimidine-4,6,11(5)-triones () and substituted 5,5'-(1,4-phenylene)bis(2-oxo-/thioxo-2,3-dihydro-1-benzo[6,7]chromeno[2,3-]pyrimidine-4,6,11(5)-trione) derivatives () has been developed based on a three-component reaction between barbituric acid/,-dimethylbarbituric acid/2-thiobarbituric acid (), aromatic aldehydes (), and 2-hydroxy-1,4-naphthoquinone () 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.

摘要

基于巴比妥酸/α,α-二甲基巴比妥酸/2-硫代巴比妥酸()、芳香醛()和2-羟基-1,4-萘醌()在室温(25-30°C)下于乙醇水溶液中进行的三组分反应,已开发出一种简单、无催化剂、直接且高效的一锅法合成一系列具有药学意义的新型功能化5-芳基-2-氧代-/硫代-2,3-二氢-1-苯并[6,7]色烯并[2,3-]嘧啶-4,6,11(5)-三酮()和取代的5,5'-(1,4-亚苯基)双(2-氧代-/硫代-2,3-二氢-1-苯并[6,7]色烯并[2,3-]嘧啶-4,6,11(5)-三酮)衍生物()的方法。该方法的显著特点是反应条件温和、无需催化剂、无需柱色谱纯化、产率优异、原子经济性高、环境友好、产物易于分离以及反应介质可重复使用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/a917/6641957/70413937840c/ao-2017-00791b_0001.jpg

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