Silver-catalyzed cascade reactions of 3-cyanochromone with 1,1-enediamines: synthesis of highly functionalized 2-(pyridin-3-yl)-chromeno[2,3-d]pyrimidines

被引：11

作者：

Xiao, Qiang ^{[1
]}

Liu, Jin ^{[1
]}

Nie, Jia-Hui ^{[1
]}

Kong, Ling-Bin ^{[1
]}

Lin, Jun ^{[1
]}

Yan, Sheng-Jiao ^{[1
]}

机构：

[1] Yunnan Univ, Key Lab Med Chem Nat Resource, Minist Educ & Yunnan Prov, Sch Chem Sci & Technol, Kunming 650091, Yunnan, Peoples R China

来源：

ORGANIC CHEMISTRY FRONTIERS | 2020年 / 7卷 / 15期

基金：

中国国家自然科学基金;

关键词：

IN-VITRO; DERIVATIVES; DISCOVERY; INHIBITORS; APOPTOSIS; DESIGN; SERIES; VIVO;

D O I：

10.1039/d0qo00388c

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel protocol for the construction of highly functionalized 2-(pyridin-3-yl)-chromeno[2,3-d]pyrimidines (PCPMDs) from 3-cyanochromone with 1,1-enediaminesviaan unprecedented cascade reaction has been developed by simply refluxing a mixture of 3-cyanochromone1and various types of 1,1-enediamines2under the catalysis of silver carbonate. As a result, a series of PCPMDs3were obtained through a novel cascade reaction involving an amazing electrocyclization mechanism of a cyano group with alpha,beta-unsaturated nitriles. This reaction formation of PCPMDs was accompanied by the formation of four bonds and the cleavage of one bond in one step. This protocol can be used for the synthesis of various pyridin-3-yl-substituted complex pyrimidine derivatives, and it is suitable for combinatorial and parallel syntheses of PCPMD drugs or natural-like products.

引用

页码：2035 / 2039

页数：5

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