Lewis Acid Catalyzed [4+2] Cycloaddition of N-Tosylhydrazones with ortho-Quinone Methides

被引：23
|
作者：
Wang, Chun-Ying [1 ]
Han, Jia-Bin [1 ]
Wang, Long [1 ]
Tang, Xiang-Ying [1 ]
机构：
[1] Huazhong Univ Sci & Technol, Sch Chem & Chem Engn, Hubei Key Lab Bioinorgan Chem & Mat Med, Key Lab Mat Chem Energy Convers & Storage, 1037 Luoyu Rd, Wuhan 430074, Hubei, Peoples R China
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 21期
基金：
中国国家自然科学基金;
关键词：
METAL-FREE SYNTHESIS; X-H X; TRANSITION-METAL; CONSTRUCTION; CYCLOPROPANATION; CYCLIZATION; ACTIVATION; ALKYLATION; PORPHYRIN; PYRAZOLES;
D O I：
10.1021/acs.joc.9b02040
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A formal [4 + 2] cycloaddition of N-tosylhydrazones with ortho-quinone methides was developed, affording the facile synthesis of diverse 1,3-oxazine derivatives under mild conditions. In this transformation, N-tosylhydrazones are used as a 1,2-dipole synthon under base-free conditions. Moreover, the substrate scope is broad, and the products are formed with high diastereoselectivities in most of the cases.
引用
收藏
页码：14258 / 14269
页数：12
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