Functionalized Hexahydropyrrolo[2,1-b]oxazoles from Catalyst-Free Annulation of Δ1-Pyrrolines with Electron-Deficient Propargylic Alcohols

被引：11

作者：

Oparina, Ludmila A. ^{[1
]}

Shabalin, Dmitrii A. ^{[1
]}

Mal'kina, Anastasiya G. ^{[1
]}

Kolyvanov, Nikita A. ^{[1
]}

Grishchenko, Lyudmila A. ^{[1
]}

Ushakov, Igor A. ^{[1
]}

Vashchenko, Alexander V. ^{[1
]}

Trofimov, Boris A. ^{[1
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Branch, 1 Favorsky Str, Irkutsk 664033, Russia

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 2020卷 / 27期

关键词：

1-Pyrrolines; Electron-deficient propargylic alcohols; Nucleophilic addition; Annulation; Pyrrolo[2; 1-b]oxazoles; RACEMIC BICYCLIC LACTAMS; ACETYLENE HYDROXY-ACIDS; ASYMMETRIC-SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; 5-HYDROXY-DELTA(1)-PYRROLINES; METHOXYCARBONYLATION; CONSTRUCTION; PYRROLIDINES; DERIVATIVES; KETOXIMES;

D O I：

10.1002/ejoc.202000582

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Electron-deficient propargylic alcohols (EWG = CN, C(O)Ph, CO2Me, C(O)NH2) under catalyst-free mild conditions are annulated with Delta 1-pyrrolines to afford functionalized hexahydropyrrolo[2,1-b]oxazoles, mostly in 19-93 % yield. The synthesis is stereoselective with respect to disposition of functionalized ethenyl group relative to the condensed heterocyclic system thus formed in most cases. This methodology provides a simple one-pot access to a novel family of synthetically and pharmaceutically prospective.

引用

页码：4181 / 4192

页数：12

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