One-pot 'on-solvent' multicomponent protocol for the synthesis of medicinally relevant 4H-pyrano[3,2-c]quinoline scaffold

被引：23

作者：

Vereshchagin, Anatoly N. ^{[1
]}

Elinson, Michail N. ^{[1
]}

Nasybullin, Ruslan F. ^{[1
]}

Ryzhkov, Fedor V. ^{[1
]}

Bobrovsky, Sergey I. ^{[1
]}

Bushmarinov, Ivan S. ^{[2
]}

Egorov, Mikhail P. ^{[1
]}

机构：

[1] N. D. Zelinsky Institute of Organic Chemistry, Leninsky prospect 47, Moscow

[2] A. N. Nesmeyanov Institute of Organoelement Compounds, Vavilova Str. 28, Moscow

来源：

Helvetica Chimica Acta | 2015年 / 98卷 / 08期

关键词：

Cell death - Scaffolds;

D O I：

10.1002/hlca.201500026

中图分类号：

学科分类号：

摘要：

'One-pot' AcONa-catalyzed transformation of salicylaldehydes, malononitrile and 4-hydroxy-1-methylquinolin-2(1H)-one in the presence of a minimal quantity of EtOH results in fast (3 min) and efficient formation of unknown 2-amino-4-(2-hydroxyaryl)-6-methyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carbonitriles in 85-98% yields, which are potential pharmaceutical agents for treating disorders responsive to the induction of apoptosis, antiproliferation, or vascular disruption. This efficient 'on-solvent' approach to the 4H-pyrano[3,2-c]quinoline scaffold represents a novel synthetic concept for multicomponent reaction (MCR) strategy and allows to combine the synthetic virtues of conventional MCR with ecological benefits and convenience of facile 'on-solvent' procedure. Copyright © 2015 Verlag Helvetica Chimica Acta AG, Zürich.

引用

页码：1104 / 1114

页数：10

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