One-Pot Synthesis of Unsymmetrical Bis-Heterocycles: Benzimidazole-, Benzoxazole-, and Benzothiazole-Linked Thiazolidines

ACS Comb Sci. 2020 Jan 13;22(1):42-48. doi: 10.1021/acscombsci.9b00161. Epub 2019 Dec 9.

Abstract

A one-pot, three-component synthesis of benzimidazole-linked thiazolidines from 2-cyanomethyl benzimidazole, iso-, isothio-, or isoselenocyanates and 1,2-dichloroethane is reported. Isolation of the key intermediate formed during the course of the reaction validates its mechanistic pathway. Under the same reaction conditions, benzimidazole-linked/fused thiazinanes were obtained when 1,3-dichloropropane or diiodomethane was used.

Keywords: benzimidazoles; combinatorial chemistry; microwave irradiation; molecular diversity; one-pot reaction; three-component synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemical synthesis*
  • Benzothiazoles / chemical synthesis*
  • Ethylene Dichlorides / chemistry
  • Hydrocarbons, Iodinated / chemistry
  • Organoselenium Compounds / chemistry
  • Propane / analogs & derivatives
  • Propane / chemistry
  • Thiazolidines / chemical synthesis*

Substances

  • Benzimidazoles
  • Benzothiazoles
  • Ethylene Dichlorides
  • Hydrocarbons, Iodinated
  • Organoselenium Compounds
  • Thiazolidines
  • isoselenocyanate
  • methylene iodide
  • ethylene dichloride
  • 1,3-dichloropropane
  • Propane