[3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1,2,4-Oxadiazinan-5-ones

doi:10.6023/cjoc201901030

Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (7): 1970-1975.DOI: 10.6023/cjoc201901030 Previous Articles Next Articles

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氮氧烯丙基正离子与肟的[3+3]环加成反应:2-N-无取代-1,2,4-噁二嗪-5-酮类化合物的合成

张智勇, 王琦, 张浩, 陈永明, 王欣, 葛泽梅, 李润涛

北京大学药学院天然药物及仿生药物国家重点实验室北京 100191

收稿日期:2019-01-20 修回日期:2019-02-28 发布日期:2019-04-08
通讯作者: 李润涛 E-mail:lirt@bjmu.edu.cn
基金资助:
国家自然科学基金（No.81673287）资助项目.

[3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1,2,4-Oxadiazinan-5-ones

Zhang Zhiyong, Wang Qi, Zhang Hao, Chen Yongming, Wang Xin, Ge Zemei, Li Runtao

a State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191

Received:2019-01-20 Revised:2019-02-28 Published:2019-04-08
Contact: 10.6023/cjoc201901030 E-mail:lirt@bjmu.edu.cn
Supported by:
Project supported by the National Natural Science Foundation of China (No. 81673287).

1. [3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1,2,4-Oxadiazinan-5-ones.PDF(2129KB)

Abstract

The first[3+3] cycloaddition reaction of in situ-generated aza-oxyallyl cations with oximes was developed. This approach provides a simple and efficient method for the synthesis of 2-N-unsubstituted 1,2,4-oxadiazin-5-one derivatives with many merits, such as easy available regents, mild reaction conditions and high yield.

Key words: 1,2,4-oxadiazinan-5-one, α-halohydroxamate, azaoxyallyl cations, oxime, [3+3]-cycloaddition

Cite this article

Zhang Zhiyong, Wang Qi, Zhang Hao, Chen Yongming, Wang Xin, Ge Zemei, Li Runtao. [3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1,2,4-Oxadiazinan-5-ones[J]. Chin. J. Org. Chem., 2019, 39(7): 1970-1975.

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氮氧烯丙基正离子与肟的[3+3]环加成反应:2-N-无取代-1,2,4-噁二嗪-5-酮类化合物的合成

[3+3] Cycloaddition Reactions of Aza-oxyallyl Cations with Oximes: Synthesis of 2-N-Unsubstituted 1,2,4-Oxadiazinan-5-ones

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