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
收藏
页码：765 / 767
页数：3
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