Highly Diastereoselective Domino Synthesis of 6-Spirosubstituted Pyrido[2,3-d]pyrimidine Derivatives in Water

被引：60

作者：

Jiang, Bo ^{[1
,2
]}

Cao, Long-Ji ^{[1
]}

Tu, Shu-Jiang ^{[1
,2
]}

Zheng, Wen-Rui ^{[3
]}

Yu, Hai-Zhu ^{[3
]}

机构：

[1] Xuzhou Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China

[2] Suzhou Univ, Coll Chem Chem Engn & Mat Sci, Suzhou 215006, Peoples R China

[3] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China

来源：

JOURNAL OF COMBINATORIAL CHEMISTRY | 2009年 / 11卷 / 04期

基金：

美国国家科学基金会;

关键词：

MICROWAVE-ASSISTED SYNTHESIS; AQUEOUS N-HETEROCYCLIZATION; ONE-POT SYNTHESIS; MULTICOMPONENT REACTIONS; 3-COMPONENT SYNTHESIS; ARYL CHLORIDES; DIELS-ALDER; REARRANGEMENT; EFFICIENT; ACID;

D O I：

10.1021/cc900038g

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

A highly diastereoselective domino reaction of 2,6-diaminopyrimidine-4-one with structurally diverse aryl aldehydes and various barbituric acids in water under microwave irradiation is described. The products arc 6-spiro-substituted pyrido[2,3-d]pyrimidines with high diastereoselectivities (up to 99: 1) in which the major diastereomer bears a cis relationship between substituents at the 5- and 7-positions. Furthermore, the mechanism for diastereoselectivity was confirmed by DFT (B3LYP) calculations.

引用

页码：612 / 616

页数：5

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