Green Approach for the Synthesis of a New Class of Diamidomethane‐linked Benzazolyl Pyrazoles and Evaluation as Antifungals

Green Approach for the Synthesis of a New Class of Diamidomethane‐linked Benzazolyl Pyrazoles and Evaluation as Antifungals

A new class of diamidomethane‐linked benzoxazolyl pyrazoles, benzothiazolyl pyrazoles, and benzimidazolyl pyrazoles were synthesized from the synthetic intermediates N‐benzazolylcarbamoylmethylcinnamides adopting environmentally benign methods. In fact, nitrile imine was generated from araldehyde ph...

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Bibliographic Details
Published in:Journal of heterocyclic chemistry Vol. 56; no. 8; pp. 2080 - 2089
Main Authors: Sowdari, Jyothi, Gudi, Yamini, Donthamsetty, Sowmya V., Venkatapuram, Padmavathi, Adivireddy, Padmaja
Format: Journal Article
Language:English
Published: Hoboken Wiley Subscription Services, Inc 01-08-2019
Subjects:
Antifungal agents
Cetyltrimethylammonium bromide
Fungicides
Iodine
Mass spectra
NMR
Nuclear magnetic resonance
Oxidation
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Summary:A new class of diamidomethane‐linked benzoxazolyl pyrazoles, benzothiazolyl pyrazoles, and benzimidazolyl pyrazoles were synthesized from the synthetic intermediates N‐benzazolylcarbamoylmethylcinnamides adopting environmentally benign methods. In fact, nitrile imine was generated from araldehyde phenylhydrazone in the presence of iodosobenzene and cetyltrimethylammonium bromide followed by oxidation with iodine in dimethylsulfoxide. The structures of compounds were characterized by IR, 1H NMR, 13C NMR, and mass spectra. The title compounds were also evaluated for their antifungal activity. Amongst all the tested compounds benzimidazolyl pyrazolyl carboxamides (13a and 13b) were found to be potential antifungal agents.
ISSN:0022-152X
1943-5193
DOI:10.1002/jhet.3569