Highly efficient and stereoselective cycloaddition of nitrones to indolyl- and pyrrolylacrylates

被引：22

作者：

Dmitriev, Viktor A. ^{[1
]}

Efremova, Mariia M. ^{[1
]}

Novikov, Alexander S. ^{[1
]}

Zarubaev, Vladimir V. ^{[2
]}

Slita, Alexander, V ^{[2
]}

Galochkina, Anastasia, V ^{[2
]}

Starova, Galina L. ^{[1
]}

Ivanov, Andrey, V ^{[3
]}

Molchanov, Alexander P. ^{[1
]}

机构：

[1] St Petersburg State Univ, Univ Skaya Nab 7-9, St Petersburg 199034, Russia

[2] Pasteur Inst Epidemiol & Microbiol, 14 Mira Str, St Petersburg 197101, Russia

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

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 24期

基金：

俄罗斯基础研究基金会;

关键词：

Indoles; Cycloaddition; Nitrones; Isoxazolidines; 1,3-DIPOLAR CYCLOADDITION; HYDROGEN-BOND; AZOMETHINE IMINES; NITRILE OXIDES; EASY ACCESS; DIASTEREOSELECTIVITY; ISOXAZOLIDINES; DERIVATIVES; INHIBITION; COMPLEXES;

D O I：

10.1016/j.tetlet.2018.04.066

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reactions of various nitrones with indolyl- and pyrrolylacrylates proceeds regioselectively with high diastereoselectivity in the case of aldonitrones, and represents an effective method for obtaining new indolyl- and pyrrolyl-substituted isoxazolidine carboxylates stabilized by weak (C-H...O) and moderate (N-H...N) strength intramolecular hydrogen bonding. The resulting cycloadducts exhibit promising in vitro anti-influenza activities. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：2327 / 2331

页数：5

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