Synthesis of 3,6-Dihydro-2H-1,2-oxazines via Dimethylsulfoxoniurn Methylide Addition to α,β-Unsaturated Nitrones

被引：8

作者：

Hasegawa, Megumi ^{[1
]}

Suga, Takuya ^{[1
]}

Soeta, Takahiro ^{[1
]}

Ukaji, Yutaka ^{[1
]}

机构：

[1] Kanazawa Univ, Grad Sch Nat Sci & Technol, Div Mat Chem, Kanazawa, Ishikawa 9201192, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2020年 / 85卷 / 17期

基金：

日本学术振兴会;

关键词：

SULFUR YLIDES; IMINES; CYCLOADDITIONS; CYCLIZATION; CARBENE;

D O I：

10.1021/acs.joc.0c01349

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A unique and efficient formation of 3,6-dihydro-2H-1,2-oxazines starting from alpha,beta-unsaturated nitrones has been achieved. The nucleophilic addition of dimethylsulfoxonium methylide to the C=N bond of an alpha,beta-unsaturated nitrone to form an aziridine N-oxide followed by the Meisenheimer rearrangement affords 3,6-dihydro-2H-1,2-oxazine in up to 70% yield. Methylene was confirmed to be incorporated at the C-3 position of the ring. A wide range of beta-aryl-substituted alpha,beta-unsaturated nitrones were applicable to this reaction.

引用

页码：11258 / 11264

页数：7

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