Utility of 3-Chlorobenzothiophene-2-Carbonylisothiocyanate for the Synthesis of Some Novel Biheterocycles of Expected Biological Activity

Abstract

The behavior of 3-chlorobenzothiophene-2-carbonylisothiocyanate 2 towards nitrogen nucleophiles such as primary amines, substituted hydrazines, aryl hydrazines, glycine, anthranilic acid; sulfur nucleophiles such as thioglycolic acid; and oxygen nucleophiles such as substituted phenols has been investigated and found that it proceeds via isothiocyanate heterocyclization to furnish noncondensed heterocyclic compounds containing thiourea, triazole, oxazole, thiazole, and benzoxazole nuclei besides the benzo[b]thiophene nucleus. The structures of the newly synthesized compounds were elucidated on the basis of IR, ¹H NMR, and mass spectral data of the compounds, and they have been screened for antimicrobial, analgesic, and anti-inflammatory activities.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.

Keywords:

• Analgesic activity
• anti-inflammatory activity
• antimicrobial activity
• 3-chlorobenzothiophene-2-carbonylisothiocyanate

Acknowledgments

The authors are thankful to the Principal, Sahyadri Science College (Autonomous), for providing laboratory facilities to carry out the synthesis and pharmacological activity of the compounds. The authors are also thankful to Sophisticated Instrumentation Facility, Indian Institute of Science, Bangalore, India, for providing spectral data.