An electron donor-acceptor (EDA) complex-mediated oxidative radical addition/cyclization between o-cyanoarylacrylamides and thiosulfonates has been accomplished, providing direct access to sulfonylated quinoline-2,4(1H,3H)-diones. Mechanistic investigations suggest the EDA complexation between Et3N and thiosulfonate, followed by the in situ generation of R-SO2 radical, which adds to o-cyanoarylacrylamides. This is followed by cyclization, abstraction of a hydrogen atom from H2O, and imine hydrolysis to a keto group.
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Supriya Manna
Hirendra Nath Dhara
Dinabandhu Barik
The Journal of Organic Chemistry
Indian Institute of Technology Guwahati
Sanken Electric (Japan)
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Manna et al. (Tue,) studied this question.
www.synapsesocial.com/papers/69e1cdc45cdc762e9d8570aa — DOI: https://doi.org/10.1021/acs.joc.6c00114