[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
收藏
页码：795 / 799
页数：5
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