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.
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页数：6
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