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Synthesis 2021; 53(05): 971-977
DOI: 10.1055/s-0040-1706104
paper

Insertion Reaction of 2-Halo-N-allylanilines with K2S Involving Trisulfur Radical Anion: Synthesis of Benzothiazole Derivatives under Transition-Metal-Free Conditions

Xin-Yu Liu
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
,
Yan-Wei Zhao∗
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
,
Tian Jiang
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
,
Weidong Rao
b   Nanjing Forest University, Nanjing 210037, P. R. of China
,
Shun-Yi Wang  ∗
a   Key Laboratory of Organic Synthesis of Jiangsu Province, College of Chemistry, Chemical Engineering and Materials Science & Collaborative Innovation Center of Suzhou Nano Science and Technology, Soochow University, Suzhou 215123, P. R. of China
› Author AffiliationsWe gratefully acknowledge the National Natural Science Foundation of China (21971174 and 21772137), PAPD, the Major Basic Research Project of the Natural Science Foundation of the Jiangsu Higher Education Institutions (No. 16KJA150002), the Project of Scientific and Technologic Infrastructure of Suzhou (SZS201708), Soochow University, and State and Local Joint Engineering Laboratory for Novel Functional Polymeric Materials for financial support.
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Abstract

A synthesis of benzothiazole derivatives through the reaction of 2-halo-N-allylanilines with K2S in DMF is developed. The trisulfur radical anion S3·–, which is generated in situ from K2S in DMF, initiates the reaction without transition-metal catalysis or other additives. In addition, two C–S bonds are formed and heteroaromatization of benzothiazole is triggered by radical cyclization and H-shift.

Keywords

transition metal-free - trisulfur radical anion - benzothiazole derivatives - radicals - cyclization

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1706104.
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Publication History

Received: 04 November 2020

Accepted after revision: 19 November 2020

Article published online:
14 December 2020

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