One-Pot Synthesis of Multifunctionalized 1-Pyrrolines from 2-Alkyl-2H-azirines and Diazocarbonyl Compounds

被引：12

作者：

Filippov, Ilya P. ^{[1
]}

Novikov, Mikhail S. ^{[1
]}

Khlebnikov, Alexander F. ^{[1
]}

Rostovskii, Nikolai V. ^{[1
]}

机构：

[1] St Petersburg State Univ, Inst Chem, St Petersburg 199034, Russia

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2022年 / 87卷 / 13期

基金：

俄罗斯科学基金会;

关键词：

ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; RING-CLOSURE; DERIVATIVES; HETEROCYCLES; 2H-PYRROLES; CYCLIZATION; ANNULATION; PYRROLES; MICHAEL;

D O I：

10.1021/acs.joc.2c00977

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel strategy for the synthesis of 1-pyrrolines based on formal [4 + 1] annulation of 2-alkyl-2H-azirines with diazocarbonyl compounds has been developed. This one-pot approach includes the Rh(II)-catalyzed formation of 4-alkyl-2-azabuta-1,3-dienes, followed by the DBU-promoted cyclization, and features a good substrate tolerance. The 1-pyrrolines containing an ester group at the C3 were prepared in a three-step one-pot procedure starting from 5-alkoxyisoxazoles. The cyclization of 2-azabutadienes to 1-pyrrolines most likely proceeds via the 6 pi electrocyclization of a conjugated NH-azomethine ylide.

引用

页码：8835 / 8840

页数：6

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