An Efficient and Green Synthesis of Highly Substituted N‐Amino‐2‐oxo‐nicotinonitriles and Their Sulfonamide Derivatives under Ultrasonic and Microwave Irradiation

An efficient and facile approach has been described for the synthesis of a new series of 1‐amino‐2‐oxo‐nicotinonitriles and their sulfonamides under microwave and ultrasonic irradiation. The desired compounds 4 a‐l were obtained via condensation of p‐chlorobenzaldehyde, aryl or heteroaryl methyl ket...

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Bibliographic Details
Published in:ChemistrySelect (Weinheim) 2019-11, Vol.4 (41), p.12151-12155
Main Authors: El‐sayed, Hassan A., Assy, Mohamed G., Mohamed, Asaad S.
Format: Article
Language:English
Subjects:
2-Oxonicotinonitrile
Microwave
One pot reaction
Sulfonamide
Ultrasonic
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Summary:An efficient and facile approach has been described for the synthesis of a new series of 1‐amino‐2‐oxo‐nicotinonitriles and their sulfonamides under microwave and ultrasonic irradiation. The desired compounds 4 a‐l were obtained via condensation of p‐chlorobenzaldehyde, aryl or heteroaryl methyl ketone and cyanoacetohydrazide in the presence of catalytic piperidine under three synthetic methodologies (namely, conventional method, ultrasonic and microwave irradiation), the best results (short reaction times, pure products, high yield) were obtained by ultrasonic irradiation. Sulfonamides 5 a‐f resulted via reaction of amines 4 a‐e and 4 j with benzene sulfonyl chloride in the presence of pyridine. The synthesized compounds give no significant results when investigated against Gm (+ve) and Gm (‐ve) bacteria, and fungi strains. Some new nicotinonitriles and their sulfonamide derivatives were one‐pot synthesized via ultrasonic and microwave irradiation as green approaches. The synthesized compounds have no significant antimicrobial activity.
ISSN:2365-6549
2365-6549
DOI:10.1002/slct.201903180