Cyclization Reactions of In Situ-Generated Acyl Ketene with Ynones to Form Oxacycles

被引：4

作者：

Perera, Erandi Liyanage ^{[1
]}

Wink, Donald J. ^{[1
]}

Luo, Yanshu ^{[2
]}

Xia, Yuanzhi ^{[2
]}

Lee, Daesung ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Chicago, IL 60607 USA

[2] Wenzhou Univ, Coll Chem & Mat Engn, Wenzhou 325035, Zhejiang, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2024年 / 89卷 / 07期

关键词：

ENDOPHYTIC FUNGUS; CATALYZED CYCLOADDITIONS; INHIBITORY-ACTIVITY; PENICILLIUM; VERMISTATIN; 1,6-ADDITION; METABOLITES; DERIVATIVES; DIYNONES; ETHERS;

D O I：

10.1021/acs.joc.3c02711

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Acyl ketenes react with polar unsaturated functional groups to give unique heterocyclic rings, yet reactions with unpolarized unsaturated functional groups have not been reported. Herein, we describe two effective ring-forming reactions between acetyl ketene and electron-deficient alkynes. The first reaction involves in situ tethering between acetyl ketene and nucleophile-containing 1,3-diynones, which promotes sequential intramolecular 1,6/1,4-additions to generate 2-methylene-2H-pyrans in various yields (24-91%). The other involves a zwitterionic intermediate generated from acetyl ketene and DABCO, which undergoes a Michael addition with terminal alkynyl ketones to generate 3-acyl-4-pyrones (11-79%).

引用

页码：4496 / 4502

页数：7

共 30 条

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