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Tandem Thien- and Benzannulations of α‑Alkenoyl-α-alkynyl Ketene Dithioacetals with Cyanoacetates: Synthesis of Functionalized Benzo[b]thiophenes

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posted on 03.04.2015, 00:00 by Wenbo Ming, Xiaocui Liu, Lianjie Wang, Jun Liu, Mang Wang
A novel domino annulation strategy for the construction of benzo­[b]­thiophenes has been developed. In the presence of Cs2CO3 and Ag2CO3, a wide range of α-alkenoyl-α-alkynyl ketene dithioacetals readily react with cyanoacetates in CH3CN at 110 °C under N2 to afford multisubstituted benzo­[b]­thiophenes efficiently via tandem thien- and benzannulations. A plausible mechanism is also proposed.

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