Direct Synthesis of 4-Acetyl-1-alkyl-1H-pyrrol-2(5H)-ones from Difunctionalized Allyl Bromide

被引：1

作者：

Jebali, Khaoula ^{[1
]}

Arfaoui, Aicha ^{[1
]}

Saadi, Fatma ^{[1
]}

Lebreton, Jacques ^{[2
]}

Amri, Hassen ^{[1
]}

机构：

[1] El Manar Univ, Lab Select Organ Synth & Biol Act, Fac Sci, Tunis 2092, Tunisia

[2] Fac Sci & Tech, CNRS UMR, Synth Organ Lab, Nantes, France

来源：

SYNTHETIC COMMUNICATIONS | 2014年 / 44卷 / 23期

关键词：

5-Exo-trig cyclization; primary amines; Z-ethyl; 3-bromomethyl-4-oxopent-2-enoate; pyrrol-2(5H)-ones; METHYLENE-GAMMA-LACTAMS; WITTIG-HORNER REACTION; BIOLOGICAL EVALUATION; HIV PROTEASE; ANALOGS; INHIBITORS; DESIGN; DERIVATIVES; ALKALOIDS; FUMARATE;

D O I：

10.1080/00397911.2014.938273

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

We describe a simple and efficient protocol for accessing some unsaturated heterocyclic compounds in a direct evaluation of allyl bromide as Z-ethyl 3-bromomethyl-4-oxopent-2-enoate. The latter reacts with primary amines via two successive nucleophilic substitutions followed by a 5-exo-trig cyclization to produce selectively 4-acetyl-1-alkyl-1H-pyrrol-2(5H)-ones in good yields.

引用

页码：3400 / 3407

页数：8

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