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Paper | Regular issue | Vol 94, No. 11, 2017, pp.2065-2079
Published online, 3rd October, 2017
DOI: 10.3987/COM-17-13803
Synthesis of Isothiochromenes and 1,3-Dihydrobenzo[c]thiophenes by Iodine- and Hydrobromic Acid-Mediated Cyclizations of o-[(tert-Butylsulfanyl)methyl)]styrenes

Kazuhiro Kobayashi,* Takuma Ueyama, and Mai Horiuchi

*Applied Chemistry Field, Chemistry and Biotechnology Course, Department of Engineering, Graduate School of Sustainability Science, Tottori University, 4-101 Koyama-minami, Tottori 680-8552, Japan


Methods for the syntheses of 4-substituted isothiochromenes and 1,1-disubstituted 1,3-dihydrobenzo[c]thiophenes have been developed. Thus, treatment of α-substituted o-[(tert-butylsulfanyl)methyl]styrenes, derived from α-substituted o-bromostyrenes using an easily operated four-step sequence, with iodine in the presence of sodium hydrogencarbonate gave isothiochromene derivatives. These tert-butyl sulfides were treated with concentrated hydrobromic acid to give 1,3-dihydrobenzo[c]thiophene derivatives.