Jump to main content
Jump to site search

Issue 15, 2013
Previous Article Next Article

Multistep divergent synthesis of benzimidazole linked benzoxazole/benzothiazole via copper catalyzed domino annulation

Author affiliations

Abstract

An efficient, facile synthesis of structurally diverse benzimidazole integrated benzoxazole and benzothiazoles has been developed. In a multi-step synthetic sequence, 4-fluoro-3-nitrobenzoic acid was converted into benzimidazole bis-heterocycles, via the intermediacy of benzimidazole linked ortho-chloro amines. The amphiphilic reactivity of this intermediate was designed to achieve the title compounds by the reaction of various acid chlorides and isothiocyanates in a single step through the in situ formation of ortho-chloro anilides and thioureas under microwave irradiation. A versatile one pot domino annulation reaction was developed to involve the reaction of benzimidazole linked ortho-chloro amines with acid chlorides and isothiocyanates. The initial acylation and urea formation followed by copper catalyzed intramolecular C–O and C–S cross coupling reactions furnished the angularly oriented bis-heterocycles which bear a close resemblance to the streptomyces antibiotic UK-1.

Graphical abstract: Multistep divergent synthesis of benzimidazole linked benzoxazole/benzothiazole via copper catalyzed domino annulation

Back to tab navigation

Supplementary files

Publication details

The article was received on 08 Nov 2012, accepted on 24 Jan 2013 and first published on 22 Feb 2013


Article type: Paper
DOI: 10.1039/C3OB27177C
Citation: Org. Biomol. Chem., 2013,11, 2473-2481

  •   Request permissions

    Multistep divergent synthesis of benzimidazole linked benzoxazole/benzothiazole via copper catalyzed domino annulation

    J. Liao, M. Selvaraju, C. Chen and C. Sun, Org. Biomol. Chem., 2013, 11, 2473
    DOI: 10.1039/C3OB27177C

Search articles by author

Spotlight

Advertisements