Clay-catalyzed synthesis of 5-substituent 1-H-tetrazoles

✍ Scribed by Alireza Najafi Chermahini; Abbas Teimouri; Fariborz Momenbeik; Amin Zarei; Zeinab Dalirnasab; Aseyeh Ghaedi; Mostafa Roosta

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 667 KB
• Volume: 47
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.382

✦ Synopsis

Abstract

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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).