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. 2019 Jan 25;9(6):3403-3406.
doi: 10.1039/c8ra09784d. eCollection 2019 Jan 22.

DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates via C-H sulfurization: a new route to 2-aminobenzothiazoles

Guangkai Yao  1   2 , Bing-Feng Wang  1   3 , Shuai Yang  1   2 , Zhi-Xiang Zhang  1   2 , Han-Hong Xu  1   2 , Ri-Yuan Tang  1   3
Affiliations

DMSO-mediated palladium-catalyzed cyclization of two isothiocyanates via C-H sulfurization: a new route to 2-aminobenzothiazoles

Guangkai Yao et al. RSC Adv. .

Abstract

DMSO was found to activate arylisothiocyanates for self-nucleophilic addition. A subsequent intramolecular C-H sulfurization catalyzed by PdBr2 enables access to a wide range of 2-aminobenzothiazole derivatives in moderate to good yields. This is the first example of a DMSO-mediated Pd-catalyzed synthesis of 2-aminobenzothiazoles through cyclization/C-H sulfurization of two isothiocyanates.

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Conflict of interest statement

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Figures

Scheme 1
Scheme 1. Biological application and synthetic methods for the preparation of 2-aminobenzothiazoles.
Scheme 2
Scheme 2. PdBr2-catalyzed cross-reaction of two different isothiocyanates.
Scheme 3
Scheme 3. Control experiments.
Scheme 4
Scheme 4. A possible mechanism.
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