A Convenient Synthesis of 2‐Sulfanylbenzoselenazole Derivatives via the Reaction of 2‐Lithiophenyl Isothiocyanates with Selenium |
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| Authors: | Kazuhiro Kobayashi Yuki Yokoi |
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| Institution: | Division of Applied Chemistry, Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4‐101 Koyama‐minami, Tottori 680‐8552, Japan, (phone/fax: +81‐857‐315263) |
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| Abstract: | The title compounds have been prepared from 2‐bromophenyl isothiocyanates 1 . Thus, 2‐lithiophenyl isothiocyanates 2 , obtained from 1 and BuLi through Br/Li exchange, reacted with Se at ?78° to form lithium benzoselenazole‐2‐thiolates 3 , which, upon aqueous workup, afforded benzoselenazole‐2(3H)‐thiones 4 . The thiolates 3 were alkylated with reactive alkyl halides and acylated with carboxylic acid chlorides to give 2‐(alkylsulfanyl)benzoselenazoles 5 and S‐(benzoselenazol‐2‐yl) thiocarboxylates 6 , respectively. |
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| Keywords: | Isothiocyanates 2‐lithiophenyl Benzoselenazole‐2(3H)‐thiones Benzoselenazoles S‐(Benzoselenazol‐2‐yl) thiocarboxylates Lithium compounds |
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