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Clay‐catalyzed synthesis of 5‐substituent 1‐ H ‐tetrazoles
Author(s) -
Chermahini Alireza Najafi,
Teimouri Abbas,
Momenbeik Fariborz,
Zarei Amin,
Dalirnasab Zeinab,
Ghaedi Aseyeh,
Roosta Mostafa
Publication year - 2010
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.382
Subject(s) - chemistry , sodium azide , catalysis , tetrazole , nitrile , solvent , yield (engineering) , montmorillonite , substituent , reusability , organic chemistry , materials science , software , computer science , metallurgy , programming language
In this study, the possibility of 5‐substituted 1‐ H ‐tetrazoles synthesis using clays as catalyst was investigated. The reaction of a series of aromatic nitriles with sodium azide was catalyzed by montmorillonite K‐10 or kaolin clays in water or DMF as solvent. Conventional heating or ultrasonic irradiation was used to promote reaction. The amount of nitrile to sodium azide mole ratio, amount of catalyst, reaction time, and solvent type were optimized. The versatility of this method was checked by using various nitriles, which showed reasonable yields of tetrazole formation. It was found that using nitriles with electron‐withdrawing groups result in both higher yields and lower reaction times. The catalysts could be reused several times without significant loss of their catalytic activity . Compared to conventional heating, ultrasonic irradiation reduced reaction times and increased catalyst activity. The present procedure is green and offers advantages, such as shorter reaction time, simple workup, and recovery and reusability of catalyst. J. Heterocyclic Chem., (2010).