A Domino Route toward Polysubstituted Pyrroles from 2-Imidazolines and Electron-Deficient Alkynes

被引：22
|
作者：
Golantsov, Nikita E. [1 ]
Golubenkova, Alexandra S. [1 ]
Festa, Alexey A. [1 ]
Varlamov, Alexey V. [1 ]
Voskressensky, Leonid G. [1 ]
机构：
[1] Peoples Friendship Univ Russia, Sci Fac, Organ Chem Dept, RUDN Univ, Moscow 117198, Russia
来源：
ORGANIC LETTERS | 2020年 / 22卷 / 12期
基金：
俄罗斯科学基金会;
关键词：
AMINO-CLAISEN REARRANGEMENT; SUBSTITUTED PYRROLES; EFFICIENT SYNTHESIS; CYCLIZATION; ALKALOIDS;
D O I：
10.1021/acs.orglett.0c01530
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 1,2-disubstituted 2-imidazolines with electron-deficient alkynes proceeds as a pseudo-threecomponent process and forms imidazolidines with an N-vinylpropargylamine fragment. Heating the resulting imidazolidines in xylene on air leads to an effective formation of polysubstituted pyrroles through a domino sequence of aza-Claisen rearrangement/transannular nucleophilic addition/oxidative ring opening reactions. The direct one-pot transformation of 2-imidazolines to pyrroles has been also realized.
引用
收藏
页码：4726 / 4731
页数：6
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