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Synthesis of amide‐linked benzazolyl isoxazoles adopting green methods and evaluation as antimicrobials
Author(s) -
Sowdari Jyothi,
Thata Sreenivasulu,
Gudi Yamini,
Venkatapuram Padmavathi,
Adivireddy Padmaja
Publication year - 2020
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3916
Subject(s) - chemistry , antimicrobial , nitrile , bromide , antifungal , amide , proton nmr , antibacterial activity , cycloaddition , organic chemistry , dimethyl sulfoxide , combinatorial chemistry , carbon 13 nmr , bacteria , catalysis , medicine , dermatology , biology , genetics
Some new benzoxazolyl isoxazoles, benzothiazolyl isoxazoles and benzimidazolyl isoxazoles connected by amide bonds ( 7‐9 ) were prepared from N ‐benzazolylcarbamoylmethylcinnamamides ( 1‐3 ) adopting eco‐friendly synthetic methodologies. In fact, cycloaddition of nitrile oxide generated from araldoxime using iodosobenzene and cetyltrimethylammonium bromide to 1‐3 followed by treatment with iodine in dimethyl sulfoxide led to the formation of title compounds with good yields and in shorter reaction times. The structures of all the synthesized compounds were confirmed by spectral parameters, viz , IR, NMR, and mass spectra and were assayed for antimicrobial activity. Among all the tested compounds, 8a and 8c displayed excellent antibacterial activity, whereas 9a and 9c showed promising antifungal activity.