A Convenient Metal-Free Method
for the Synthesis of Benzothiazolethiones from o-Haloanilines
and Carbon Disulfide

Peng Zhao; Fei Wang; Chanjuan Xi

doi:10.1055/s-0031-1289713

PSP

A Convenient Metal-Free Method for the Synthesis of Benzothiazolethiones from o-Haloanilines and Carbon Disulfide

Peng Zhao^a, Fei Wang^a, Chanjuan Xi*^a,b
^a Key Laboratory of Bioorganic Phosphorus Chemistry & Chemical Biology (Ministry of Education), Department of Chemistry, Tsinghua University, Beijing 100084, China
e-Mail: cjxi@tsinghua.edu.cn;
^b State Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China

Abstract

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Abstract

A convenient method has been developed for the preparation of a variety of 1,3-benzothiazole-2(3H)-thiones. The reaction proceeds from an o-haloaniline derivative and carbon disulfide in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene at 80-140 ˚C to give the corresponding 1,3-benzothiazole-2(3H)-thione derivatives in good-to-excellent yields.

Key words

cyclizations - heterocycles - benzothiazoles - amines - carbon disulfide - tandem reaction

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References

These compounds can exist in two tautomeric forms: the 1,3-benzothiazole-2(3H)-thione or the 1,3-benzothiazole-2-thiol. X-ray determination and calculation suggest that the 1,3-benzothiazole-2(3H)-thione tautomer is generally favored; see:

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