Three-component condensation of cyclic 1,3-dicarbonyl compounds, N-phenacylpyridinium salts, and isatins or aromatic aldehydes as a method for the synthesis of novel condensed 2-aroyl-2,3-dihydrofurans

被引：3

作者：

Osipov, Dmitry V. ^{[1
]}

Demidov, Maxim R. ^{[1
]}

Osyanin, Vitaly A. ^{[1
]}

Klimochkin, Yury N. ^{[1
]}

机构：

[1] Samara State Tech Univ, 244 Molodogvardeyskaya St, Samara 443100, Russia

来源：

CHEMISTRY OF HETEROCYCLIC COMPOUNDS | 2021年 / 57卷 / 10期

基金：

俄罗斯基础研究基金会;

关键词：

2-aroyl-2,3-dihydrofurans; 1,3-dicarbonyl compounds; isatins; pyridinium ylides; spirooxindoles; Knoevenagel reaction; Michael reaction; multicomponent reactions; DIASTEREOSELECTIVE SYNTHESIS; SPIROOXINDOLES; COUMARINS;

D O I：

10.1007/s10593-021-03020-3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Three-component condensation of in situ generated pyridinium aroylmethylides with isatins or aromatic aldehydes and cyclic 1,3-dicarbonyl compounds gave a series of condensed 2-aroyl-2,3-dihydrofurans. The reaction proceeds diastereoselectively and represents a cascade process involving the Knoevenagel condensation, the carbo-Michael reaction, and intramolecular nucleophilic substitution. The possibility of reductive rearrangement of spirocyclic furanyl-substituted oxindole into a pyran derivative by the action of zinc in acetic acid was shown.

引用

页码：1045 / 1050

页数：6

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