Aryloxy tetrazoles with axial chirality: Synthesis and partial resolution of 5-(1-(2-methoxynaphthalen-1-yl)naphthalen-2-yloxy)-1H-tetrazole

Dabbagh, Hossein A.; Chermahini, Alireza Najafi; Teimouri, Abbas

doi:10.1002/hc.20241

Cited by 5 publications

(2 citation statements)

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“…They have been used in the synthesis of 1,5-benzodiazepines [23], acetonide protection [24], alkylation of benzene [25], DielsAlder reaction [26], dihydrofuran synthesis [27], and bromination and chlorination of aromatic compounds [28]. In continuing with our research in tetrazole chemistry [29][30][31] and application of clays in organic transformations [32,33], herein we report a new process for synthesis of 1-H-5-substituted tetrazoles using clays as safe, environmentally benign, and inexpensive catalysts.…”

Section: Introductionmentioning

confidence: 99%

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

Chermahini

Teimouri

Momenbeik

et al. 2010

Journal of Heterocyclic Chem

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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.

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Section: Introductionmentioning

confidence: 99%

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

Chermahini

Teimouri

Momenbeik

et al. 2010

Journal of Heterocyclic Chem

Self Cite

View full text Add to dashboard Cite

show abstract

“…In any sense, these catalysts could keep excellent catalytic activity even after recycling and can be reused for many times. In continuing with our interest in tetrazole chemistry 29–31, herein we report a new process for the synthesis of 5‐substituted 1‐ H ‐tetrazoles using modified clays as safe, environmentally benign, and inexpensive catalysts (Scheme ).…”

Section: Introductionmentioning

confidence: 99%