A rapid and efficient route to benzazole heterocycles

Richard D. Carpenter, Mark J. Kurth

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

This protocol describes a rapid, high-yielding, microwave-mediated route that affords benzazole heterocycles in high crude purity and represents a significant advancement toward an environmentally friendly reaction. The reaction of aryl isothiocyanates with o-nucleophilic anilines produces thiourea intermediates that, in the presence of a carbodiimide-functionalized resin, cyclize to benzazoles with the safe removal of one equivalent of hydrogen sulfide. This procedure takes ĝ̂1/48.5 h to complete: 1g-3 h for setup, 4.5 h for benzazole formation and 2 h for workup and purification.

Original languageEnglish (US)
Pages (from-to)1731-1736
Number of pages6
JournalNature Protocols
Volume5
Issue number11
DOIs
StatePublished - Oct 2010

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Aniline Compounds
Isothiocyanates
Carbodiimides
Thiourea
Hydrogen Sulfide
Microwaves
Purification
Resins

ASJC Scopus subject areas

  • Biochemistry, Genetics and Molecular Biology(all)

Cite this

A rapid and efficient route to benzazole heterocycles. / Carpenter, Richard D.; Kurth, Mark J.

In: Nature Protocols, Vol. 5, No. 11, 10.2010, p. 1731-1736.

Research output: Contribution to journalArticle

Carpenter, Richard D. ; Kurth, Mark J. / A rapid and efficient route to benzazole heterocycles. In: Nature Protocols. 2010 ; Vol. 5, No. 11. pp. 1731-1736.
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