Synthesis of 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones or 1-hydroxy-1,6-dihydropylidine-2,5-diones from N-hydroxy-N-(2-oxoalkyl) amides

被引：5

作者：

Kulakov, Ivan V. ^{[1
]}

Nikolaenkova, Elena B. ^{[2
]}

Gatilov, Yuri V. ^{[2
,3
]}

Tikhonov, Alexsei Ya. ^{[2
]}

Fisyuk, Alexander S. ^{[1
,4
]}

机构：

[1] Omsk FM Dostoevsky State Univ, Dept Organ Chem, Omsk 644077, Russia

[2] NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

[3] Novosibirsk State Univ, Novosibirsk 630090, Russia

[4] Omsk State Tech Univ, Lab New Organ Mat, Omsk 644050, Russia

来源：

TETRAHEDRON LETTERS | 2015年 / 56卷 / 44期

关键词：

Hydroxamic acid; Intramolecular cyclization; Oxidation reaction; 1,5-Dihydro-2H-pyrrol-2-ones; 1,6-Dihydropyridine-2,5-diones; DERIVATIVES; 5,6-DIHYDROPYRIDIN-2(1H)-ONES; SIDEROPHORE; CYCLIZATION; CEPABACTIN;

D O I：

10.1016/j.tetlet.2015.09.030

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Efficient methods for the preparation of 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones and 1-hydroxy-1,6-dihydropyridine-2,5-diones from N-hydroxy-N-(2-oxoalkyl)amides are reported. It was found that the reaction of N-hydroxy-N-(2-oxoalkyl)amides with 3 equiv of potassium tert-butoxide led to 1-hydroxy-1,5-dihydro-2H-pyrrol-2-ones. A decrease of the base content to 1.5 equiv or less led to an increase of 1-hydroxy-3-phenyl-1,6-dihydropyridine-2,5-dione in the reaction due to oxidation of the starting materials by atmospheric oxygen and their subsequent transformation. (C) 2015 Elsevier Ltd. All rights reserved.

引用

页码：5980 / 5981

页数：2

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