Copper-Catalyzed Cascade Bicyclization of o-Alkenylphenyl Isothiocyanates with Sodium Azide Leading to the 5H-Benzo[d]tetrazolo[5,1-b] [1,3]thiazines

doi:10.6023/cjoc201912036

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (8): 2426-2432.DOI: 10.6023/cjoc201912036 Previous Articles Next Articles

铜催化邻烯基芳基异硫氰酸酯与叠氮化钠串联双环化反应合成5H-苯并四氮唑并噻嗪化合物

张亚辉, 刘洋, 缪建康, 郝文燕

江西师范大学化学化工学院功能有机小分子教育部重点实验南昌 330022

收稿日期:2019-12-25 修回日期:2020-05-12 发布日期:2020-05-28
通讯作者: 郝文燕 E-mail:wenyanhao@jxnu.edu.cn
基金资助:
国家自然科学基金（No.21762023）、江西省自然科学基金（No.2018BAB203006）和江西省教育厅（No.GJJ160285）资助项目.

Copper-Catalyzed Cascade Bicyclization of o-Alkenylphenyl Isothiocyanates with Sodium Azide Leading to the 5H-Benzo[d]tetrazolo[5,1-b] [1,3]thiazines

Zhang Yahui, Liu Yang, Miao Jiankang, Hao Wenyan

Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry&Chemical Engineering, Jiangxi Normal University, Nanchang 330022

Received:2019-12-25 Revised:2020-05-12 Published:2020-05-28
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21762023), the Natural Science Foundation of Jiangxi Province (No. 2018BAB203006) and the Research Fund of Jiangxi provincial Education Department (No. GJJ160285).

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Abstract

A simple and efficient method for the preparation of 5H-benzo[d]tetrazolo[5,1-b] [1,3]thiazines has been developed. The transformation involved the copper(I)-catalyzed cascade bicyclization of o-alkenylphenyl isothiocyanates with sodium azide to afford corresponding products in moderate to good yields. This present strategy provides an effective way to construct small molecular N-, and S-heterocycles.

Key words: copper-catalysis, cascade bicyclization, 5H-benzo[d]tetrazolo[5,1-b] [1,3]thiazine, o-alkenylphenyl isothiocyanate

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Zhang Yahui, Liu Yang, Miao Jiankang, Hao Wenyan. Copper-Catalyzed Cascade Bicyclization of o-Alkenylphenyl Isothiocyanates with Sodium Azide Leading to the 5H-Benzo[d]tetrazolo[5,1-b] [1,3]thiazines[J]. Chinese Journal of Organic Chemistry, 2020, 40(8): 2426-2432.

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铜催化邻烯基芳基异硫氰酸酯与叠氮化钠串联双环化反应合成5H-苯并四氮唑并噻嗪化合物

Copper-Catalyzed Cascade Bicyclization of o-Alkenylphenyl Isothiocyanates with Sodium Azide Leading to the 5H-Benzo[d]tetrazolo[5,1-b] [1,3]thiazines

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