Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,400 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.