Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides

doi:10.6023/cjoc202108016

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (2): 507-518.DOI: 10.6023/cjoc202108016 Previous Articles Next Articles

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苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的烯丙基化反应研究

王凤, 黄丹凤^*(), 赵鹏飞, 杨明, 韩侗育, 王克虎, 王君姣, 苏瀛鹏, 胡雨来^*()

西北师范大学化学化工学院兰州 730070

收稿日期:2021-08-13 修回日期:2021-09-30 发布日期:2022-02-24
通讯作者: 黄丹凤, 胡雨来
基金资助:
国家自然科学基金(21861033); 国家自然科学基金(22061037); 上海恩氟佳科技有限公司资助项目.

Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides

Feng Wang, Danfeng Huang(), Pengfei Zhao, Ming Yang, Tongyu Han, Kehu Wang, Junjiao Wang, Yingpeng Su, Yulai Hu()

College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou 730070

Received:2021-08-13 Revised:2021-09-30 Published:2022-02-24
Contact: Danfeng Huang, Yulai Hu
Supported by:
National Natural Science Foundation of China(21861033); National Natural Science Foundation of China(22061037); Shanghai Sinofluoro Chemicals Co., Ltd.

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Abstract

The allylation of benzol[e][1,2,3]oxathiazine-2,2-dioxides with allyl bromides promoted by tin powder was explored. The results showed that the allylation proceeded smoothly with high yields for a variety of substrates. When various allyl bromides were used to perform the reaction, the γ-addition products were obtained. These allylated products underwent N-allylation reaction in the presence of base, and the diallylated products of benzol[e][1,2,3]oxathiazine-2,2-dioxides were obtained in high yields. The diallylated products of benzol[e][1,2,3] oxathiazine-2,2-dioxides further underwent ring closing metathesis reaction, and the cyclic derivatives of benzol[e][1,2,3] oxathiazine-2,2-dioxides were obtained in good yield.

Key words: tin powder, allyl bromides, benzol[e][1,2,3]oxathiazine-2,2-dioxides, allylation

Cite this article

Feng Wang, Danfeng Huang, Pengfei Zhao, Ming Yang, Tongyu Han, Kehu Wang, Junjiao Wang, Yingpeng Su, Yulai Hu. Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides[J]. Chinese Journal of Organic Chemistry, 2022, 42(2): 507-518.

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Fig. & Tab. 6

Scheme 1. Allylation reaction of benzol[e][1,2,3]oxathiazine 2,2-dioxides

Entry	Molar ratio of 1a/2/3a	Solvent	Yield^b/%
1	1/2/1.5	THF	88
2	1/2/2	THF	91
3^c	1/2/2.5	THF	98
4	1/2/3	THF	96
5	1/1.5/2.5	THF	92
6	1/2.5/2.5	THF	93
7	1/2/2.5	CH₃CH₂OH	57
8	1/2/2.5	1,4-Dioxane	91
9	1/2/2.5	H₂O	27
10	1/2/2.5	DCE	65
11	1/2/2.5	CH₃CN	62
12	1/2/2.5	Toluene	74
13	1/2/2.5	DCM	0

Table 1. Optimization of reaction conditions of tin powder- promoted allylation

Table 2. Allylation reaction of benzol[e][1,2,3] oxathiazine-2,2-dioxides promoted by tin powder

Table 3. Allylation reaction of products 4 in the presence of base

Table 4. Allylation reaction of products 4 in the presence of base

Scheme 2. Proposed reaction mechanism of allylation promoted by tin powder

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苯并[e][1,2,3]噁噻嗪-2,2-二氧化物的烯丙基化反应研究

Study on the Allylation of Benzol[e][1,2,3]oxathiazine-2,2-dioxides

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Fig. & Tab. 6

References 21

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