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Paper | Special issue | Vol 95, No. 1, 2017, pp.200-209
Published online, 7th June, 2016
DOI: 10.3987/COM-16-S(S)3
Synthesis of 3-Bromoquinoline-2(1H)-thiones and 2-(Alkylsulfanyl)-3-bromoquinolines Based on the Reaction of 2-(2,2-Dibromoethenyl)phenyl Isothiocyanates with Butyllithium

Kazuhiro Kobayashi,* Ippei Nozawa, and Takashi Nogi

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


The synthesis of 3-bromoquinoline-2(1H)-thiones and 2-(alkylsulfanyl)-3-bromoquinolines from readily available starting materials was accomplished. Thus, 2-(2,2-dibromoethenyl)phenyl isothiocyanates were treated with butyllithium to afford, after aqueous workup, 3-bromoquinoline-2(1H)-thiones. When haloalkanes were added prior to workup, 2-(alkylsulfanyl)-3-bromoquinolines were obtained. An elaboration of one of these compounds to a thieno[2,3-b]quinoline derivative and one-pot preparation of 3-substituted quinoline-2(1H)-thiones were also achieved.