Facile three-component reactions for the synthesis of N-unsubstituted 1H-pyrrol-3(2H)-ones and base induced divergent N-H and C-C bond derivatizations

被引：4

作者：

Cao, Jia-xuan ^{[1
]}

Hua, Wei-jie ^{[1
]}

Jiang, Jun-cen ^{[1
]}

Chen, Min ^{[1
]}

Sha, Qiang ^{[1
]}

机构：

[1] Nanjing Agr Univ, Coll Sci, Dept Chem, Jiangsu Key Lab Pesticide Sci, 1 Weigang Rd, Nanjing 210095, Peoples R China

来源：

TETRAHEDRON | 2022年 / 125卷

关键词：

Heterocycles; Multicomponent reactions; Cascade reactions; 2; 3-Diketoesters; Rearrangement reactions; METAL-FREE SYNTHESIS; CYCLIZATION; CHEMISTRY; DERIVATIVES; CASCADE; PYRROLIN-4-ONES; ALKALOIDS; MIGRATION; EFFICIENT; DESIGN;

D O I：

10.1016/j.tet.2022.133038

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Herein, we present a facile three-component reaction of 2,3-diketoesters, ammonium acetate and ke-tones that yielded a variety of N-unsubstituted 1H-pyrrol-3(2H)-ones in moderate to good yields. Sub-sequently, base-induced divergent N-H and C-C bond derivatizations of N-unsubstituted 1H-pyrrol-3(2H)-ones were revealed. By using NaH as the base, N-alkylation, acylation and sulfonylation occur smoothly. When NaOH is used, C-C(1/4O) cleavage occurs and further Michael addition reaction happens, resulting in the installation of an alkyl chain at the 2-position of the 1H-pyrrol-3(2H)-one skeleton.(c) 2022 Elsevier Ltd. All rights reserved.

引用

页数：6

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