Abstract
A series of 5-substituted 1H-tetrazole were efficiently prepared by InCl3catalyzed (10 mol %) from structurally divert organic nitriles with sodium azide under the influence of microwave irradiation. The present protocol was successfully applied to the aliphatic, aryl, benzylic and heterocyclic nitriles and corresponding 5-substituted 1H-tetrazole were obtained in good to excellent yield (70-96%). This method gives remarkable advantages such as short reaction time, simple work-up procedure and economical beneficial.
Highlights
The growing interest in heterocyclic compounds and their methods for synthesis are of paramount importance to medicinal, chemical and agricultural research because they make novel materials with unique properties
Attention towards synthesis of tetrazole and its analogues has been constantly increased because of a number of highly efficient drugs based on tetrazole.[1]
With these results in hand we investigated catalytic amount required for this transformation and found that 10 mol% of InCl3 (Table 1, entry 13) catalyst gives excellent yield (95 %)
Summary
The growing interest in heterocyclic compounds and their methods for synthesis are of paramount importance to medicinal, chemical and agricultural research because they make novel materials with unique properties. 5-((4-methoxyphenyl)methyl) tetrazole (2l): White solid with 71 % yield; IR (KBr): νmax 3105 (m, C-H), 2966-2484 (brs, N-H), 1610 (s, C=C), 1512 (s, tetrazole),1247 (s, CH2), 848 (s, p-disubstituted benzene) cm-1; 1H NMR (400 MHz, DMSO-d6) δ: 7.19 (d, J = 8.4 Hz, 2H), 6.88 (d, J = 8.8 Hz, 2H), 4.21(s, 2H), 3.75 (s, 3H); LC/MS: m/z =191 (100)[M+H]+ , 121 (27) [M-CHN4]+ ; HRMS calc.
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