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Paper | Regular issue | Vol 83, No. 6, 2011, pp.1303-1313
Published online, 13th April, 2011
DOI: 10.3987/COM-11-12180
Synthesis of 3,1-Benzothiazines from 2-Alkenyl- and 2-Alkynylanilides and Lawesson Reagent

Kentaro Okuma,* Saori Ozaki, Noriyoshi Nagahora, and Kosei Shioji

*Department of Chemistry, Faculty of Sciences, Fukuoka University, 8-19-1 Nanakuma, Jonan-ku, Fukuoka 814-0180, Japan


Reaction of 2-vinylacetanilide with P4S10 gave 2-vinylthioacetanilide, whereas reaction of 2-vinylacetanilide with Lawesson reagent (LR) afforded 2,4-dimethyl-4H-3,1-benzothiazine in 62% yield. Reaction of 2-alkynylanilides with LR gave 4-exomethylene-4H-3,1-benzothiazines in good yields.