A base-promoted nucleophilic ring-opening reaction of 3-chloro-1,2-benzisothiazole for the synthesis of 2-cyanoaryl sulfides was developed. This method proceeds under mild conditions with operational simplicity. Using Cs2CO3 as the base and without the need for any metal catalyst, the ring-opening reactions of 3-chloro-1,2-benzisothiazole with three types of nucleophiles—namely indoles, 2-naphthols, and nitromethane—were achieved, affording 27 examples of 2-cyanoaryl sulfides in up to 99% yield. Some of the obtained compounds exhibited good antifungal activity; notably, compound 3d displayed excellent inhibitory activity against the phytopathogenic fungus Botrytis cinerea (B. cinerea), with an EC50 value of 0.445 μg/mL. These results fully demonstrate the promising application prospects of this synthetic method and the resulting products.
Liu Yilin
,
Ma Qichen
,
Zhu Xinxin
,
Luo Jianghao
,
Wang Fang
,
Li Mengyang
,
Lin Xiaobin
. Nucleophilic Ring-Opening of 3-Chloro-1,2-benzisothiazoles to Synthesize 2-Cyanoaryl Sulfides and Antifungal Activity Studies[J]. Chinese Journal of Organic Chemistry, 0
: 202606010
-202606010
.
DOI: 10.6023/cjoc202606010
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