Synthesis of 4,7-dibromobenzo[b]thiophene derivatives via 2-(1-adamantylsulfanyl)-1,4-dibromo-3-(ethynyl)-benzenes and their reactions

Kozo Toyota, Shinichi Mikami, Hiroki Tanaka, Shuhei Yoshida, Kazuma Iwai, Kenta Takahashi, Hiroki Kishi, Yota Kikuchi, Koya Saito, Homa Yamaguchi, Hirotaka Mutoh

Research output: Contribution to journalArticlepeer-review

Abstract

Mild Corey-Fuchs reaction conditions using dimethyl sulfoxide - aqueous KOH solution at room temperature were applied to preparation of 2-(1-adamantylsulfanyl)-1,4-dibromo-3-(ethynyl)benzene. Various substituents were introduced to the terminal alkyne moiety of the (ethynyl)(sulfanyl)benzene, either by substitution reaction or by Sonogashira cross coupling. The alkynes thus obtained were converted to the corresponding 4,7-dibromobenzo[b]thiophene derivatives by the ‘silica gel-assisted cyclization’ method. Reactions of 4,7-dibromobenzo[b]thiophene and 2,4,7-tribromobenzo[b]thiophene were also investigated.

Original languageEnglish
Pages (from-to)1763-1784
Number of pages22
JournalHeterocycles
Volume100
Issue number11
DOIs
Publication statusPublished - 2020

ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis of 4,7-dibromobenzo[b]thiophene derivatives via 2-(1-adamantylsulfanyl)-1,4-dibromo-3-(ethynyl)-benzenes and their reactions'. Together they form a unique fingerprint.

Cite this