Regiospecific Syntheses of 3-Aza-α-carbolines via Inverse Electron-Demand Diels-Alder Reactions of 2-Aminoindoles with 1,3,5-Triazines

被引：16
作者：
Xu, Guoxing
Zheng, Lianyou
Wang, Shixue
Dang, Qun [1 ]
Bai, Xu
机构：
[1] Jilin Univ, Ctr Combinatorial Chem & Drug Discovery, Coll Chem, Changchun 130012, Jilin, Peoples R China
来源：
SYNLETT | 2009年 / 19期
基金：
中国国家自然科学基金;
关键词：
2-aminoindoles; inverse electron-demand Diels-Alder reactions; heterocycles; 3-aza-alpha-carbolines; regiospecific syntheses; SUBSTITUTED ALPHA-CARBOLINES; 4+2 CYCLOADDITION REACTIONS; MICROBIAL TRANSFORMATION; ISO-CARBOLINES; AZACARBAZOLES; DIENOPHILES; CONVERSION; INDOLE;
D O I：
10.1055/s-0029-1218345
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The scope of 1,3,5-triazine inverse electron-demand Diels-Alder (IDA) reactions was expanded to include 2-aminoindoles as productive dienophiles leading to various 3-aza-alpha-carbolines in excellent yields. Furthermore. the two ester groups of the IDA product were differentiated via reduction of the C4-ester to its corresponding alcohol. This new IDA reaction could be potentially applied to the synthesis of various 3-aza-mescengrincin analogues that may possess neuroprotective activities.
引用
收藏
页码：3206 / 3210
页数：5
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