Synthesis of Dihydrobenzoxazine-Fused Spirooxazoline-4-ones via [3+2] Cycloaddition of Azaoxyallyl Cations with Vinyl Benzoxazinanones

被引:16
作者
Kim, Eunjin [1 ]
Mun, Dasom [1 ]
Kim, Sung-Gon [1 ]
机构
[1] Kyonggi Univ, Dept Chem, 154-42 Gwanggyosan Ro, Suwon 16227, South Korea
基金
新加坡国家研究基金会;
关键词
spiro compounds; dihydrobenzoxazines; tetrahydroisoquinolines; cations; benzoxazinanones; AZA-OXYALLYL CATIONS; RAPID SYNTHESIS; ACCESS; ANNULATION; SYNOXAZOLIDINONES; 4-OXAZOLIDINONES;
D O I
10.1002/ajoc.201900517
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An example of a [3+2] cycloaddition reaction between azaoxyallyl cations generated in situ and a variety of vinyl benzoxazinanones has been developed. This reaction provides an attractive method for the synthesis of spirooxazoline-4-ones based on dihydrobenzoxazines, which were obtained in good yield (up to 98% yield) with high diastereoselectivity (up to >20 : 1). The synthesized spiro-bis-N,O-heterocycles can be used as building blocks toward the synthesis of other useful compounds.
引用
收藏
页码:2037 / 2041
页数:5
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