Synthesis of benzothiazoles through copper-catalyzed one-pot three-component reactions with use of sodium hydrosulfide as a sulfur surrogate

Namjin Park, Yumi Heo, Manian Rajesh Kumar, Yong Kim, Kwang Ho Song, Sunwoo Lee

Research output: Contribution to journalArticle

47 Citations (Scopus)

Abstract

Copper-catalyzed one-pot three-component reactions of 2-iodoanilines, aldehydes, and NaSH·n H 2O afford benzothiazoles in good yields. When CuCl was employed as a catalyst in the absence of a ligand, a variety of aromatic aldehydes and substituted 2-iodoanilines reacted with NaSH·n H 2O to produce the corresponding 2-arylbenzothiazoles in 70-98 % yields. The copper catalyst plays a key role in C-S bond formation between NaSH·n H 2O and the aryl iodide that was formed from the condensation of 2-iodoaniline and aldehyde. It was found that NaSH·n H 2O functions as a sulfur surrogate and oxidant in the formation of benzothiazole. 2-Iodoanilines, aldehydes, and NaSH·n H 2O afford benzothiazoles in a one-pot reaction in the presence of a copper catalyst. The desired products can be obtainedin moderate to good yields. The copper catalyst plays a key role in C-S bond formation between aryl iodides and NaSH·n H 2O.

Original languageEnglish
Pages (from-to)1984-1993
Number of pages10
JournalEuropean Journal of Organic Chemistry
Issue number10
DOIs
Publication statusPublished - 2012 Apr 1

Fingerprint

Benzothiazoles
aldehydes
Sulfur
Aldehydes
Copper
sulfur
sodium
catalysts
copper
Catalysts
Iodides
synthesis
iodides
Oxidants
Condensation
condensation
Ligands
ligands
sodium bisulfide
2-iodobenzenamine

Keywords

  • Copper
  • Homogeneous catalysis
  • Multicomponent reactions
  • Nitrogen heterocycles
  • Sulfur heterocycles

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry

Cite this

Synthesis of benzothiazoles through copper-catalyzed one-pot three-component reactions with use of sodium hydrosulfide as a sulfur surrogate. / Park, Namjin; Heo, Yumi; Kumar, Manian Rajesh; Kim, Yong; Song, Kwang Ho; Lee, Sunwoo.

In: European Journal of Organic Chemistry, No. 10, 01.04.2012, p. 1984-1993.

Research output: Contribution to journalArticle

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