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Paper | Regular issue | Vol 96, No. 9, 2018, pp.1570-1582
Published online, 10th August, 2018
DOI: 10.3987/COM-18-13959
An Efficient Synthesis of 4-Mono- and 4,4-Di-substituted 3,4-Dihydro-2H-1-benzothiopyran 1,1-Dioxides by LDA-Mediated Cyclization of o-(Methylsulfonyl)styrenes

Kazuhiro Kobayashi* and Takuma Ueyama

*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

Abstract

A new and efficient method for the preparation of 3,4-dihydro-2H-1-benzothiopyran 1,1-dioxide derivatives has been developed. α-Substituted o-(methylsulfonyl)styrenes, which can be derived from α-substituted o-bromostyrenes by an easily operated two-step sequence, are cyclized on treatment with lithium diisopropylamide (LDA) to give, after aqueous workup, the corresponding 4-monosubstituted 3,4-dihydro-2H-1-benzothiopyran 1,1-dioxides. Addition of electrophiles prior to aqueous workup provides 4,4-disubstituted derivatives.