A cascade reaction consisting of Pictet-Spengler-type cyclization and Smiles rearrangement: Application to the synthesis of novel pyrrole-fused dihydropteridines

被引：42

作者：

Xiang, Jinbao ^{[1
]}

Zheng, Lianyou ^{[1
]}

Chen, Feng ^{[1
]}

Dang, Qun ^{[1
]}

Bai, Xu ^{[1
]}

机构：

[1] Jilin Univ, Ctr Combinatorial Chem & Drug Discovery, Changchun 130012, Jilin, Peoples R China

来源：

ORGANIC LETTERS | 2007年 / 9卷 / 05期

关键词：

D O I：

10.1021/ol0629364

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Tandem Pictet-Spengler-type cyclization and Smiles rearrangement have been discovered in the synthesis of pyrimidine-fused heterocycles. The reaction of 4-chloro-5-pyrrol-1-ylpyrimidine amino aldehyde with an amine under an acidic condition yielded the Pictet-Spengler-type cyclization product diazepine, which readily underwent Smiles rearrangement to give a novel pyrrolo[1,2-f]pteridine derivative.

引用

页码：765 / 767

页数：3

共 32 条

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[32] Stereoselective synthesis of 1,2,3-trisubstituted 1,3-dienes through novel [3,3]-sigmatropic rearrangements in α-allenic methanesulfonates:: Application to the preparation of fused tricyclic systems by tandem rearrangement/Diels-Alder reaction
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