Highly Diastereoselective Domino Synthesis of 6-Spirosubstituted Pyrido[2,3-d]pyrimidine Derivatives in Water
Highly Diastereoselective Domino Synthesis of 6-Spirosubstituted Pyrido[2,3-d]pyrimidine Derivatives in Water
复制标题
6-螺取代吡啶并[2,3-d]嘧啶衍生物在水中的高度非对映选择性多米诺合成
DOI：
10.1021/cc900038g
复制
发表时间：
2009-07-01
影响因子：
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通讯作者：
Yu, Hai-Zhu
中科院分区：
文献类型：
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作者：
Jiang, Bo;Cao, Long-Ji;Yu, Hai-Zhu
在微波辐射下，2，6-二氨基嘧啶-4-酮与不同结构的芳香醛和巴比妥酸在水中发生了高度非对映选择性的多米诺反应。产物为6-螺环取代的吡啶并[2，3-d]嘧啶类化合物，具有高的非对映选择性（高达99：1），其中主要的非对映异构体在5-和7-位上的取代基之间具有顺式关系。通过密度泛函（B3 LYP）计算，进一步证实了反应的非对映选择性机理。
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.