[4+2]-Cycloaddition Reactions of Aza-o-quinone Methides with Fulvenes: Construction of Tetrahydroquinoline Derivatives

被引：4

作者：

Cheng, Hang ^{[1
]}

Yan, Ding-Ce ^{[2
]}

Wang, Gang ^{[1
]}

He, Zhao-Lin ^{[1
]}

机构：

[1] Wuhan Inst Technol, Engn Res Ctr Phosphorus Resources Dev & Utilizat, Sch Chem & Environm Engn, Minist Educ,Key Lab Green Chem Engn Proc,Minist T, Wuhan 430205, Peoples R China

[2] Huazhong Univ Sci & Technol, Analyt & Testing Ctr, Wuhan 430072, Peoples R China

来源：

SYNLETT | 2022年 / 33卷 / 08期

基金：

中国国家自然科学基金;

关键词：

cycloaddition; azaquinone methides; fulvenes; tetrahydroquinolines; DIELS-ALDER REACTION; INVERSE-ELECTRON-DEMAND; INTRAMOLECULAR 6+4 CYCLOADDITIONS; FACILE SYNTHESIS; STEREOSELECTIVE-SYNTHESIS; EFFICIENT SYNTHESIS; AZOMETHINE IMINES; SULFUR YLIDES; PENTAFULVENES; ANNULATION;

D O I：

10.1055/a-1796-7444

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient [4+2] cycloaddition reaction of fulvenes with aza-o-quinone methides, generated in situ from N-(o-chloromethyl)aryl sulfonamides with the assistance of a base, has been developed to afford a series of tetrahydroquinoline derivatives. The reaction tolerates a wide range of aza-o-quinone methides and fulvenes bearing four- to seven-membered rings to afford the corresponding tetrahydroquinolines in moderate to good yields. Based on a literature analysis, a plausible mechanism for this [4+2] cycloaddition is proposed.

引用

页码：795 / 799

页数：5

共 57 条

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