Elsevier

Chinese Chemical Letters

Volume 23, Issue 2, February 2012, Pages 161-164
Chinese Chemical Letters

Glycerol mediated synthesis of 5-substituted 1H-tetrazole under catalyst free conditions

https://doi.org/10.1016/j.cclet.2011.11.019Get rights and content

Abstract

We have developed simple, cost effective and environmentally benign protocol for the synthesis of 5-substituted 1H-tetrazoles via [2], [3] cycloaddition reaction from organic nitriles and sodium azide in glycerol under catalyst free condition. The corresponding 5-substituted 1H-tetrazoles were obtained with good to excellent yields (68–95%).

Section snippets

Experimental

All reagents were purchased from commercial suppliers and used without further purification. 1H NMR spectra were recorded on 400 MHz spectrometer and were expressed in ppm downfield from TMS as internal standard, MS analysis was carried out under ESI mode or LCMS spectrometer and IR spectra were recorded on Shimadzu model FT-IR spectrometer (KBr pellets). Melting points were determined by open-end capillary tubes method and are uncorrected. The products were purified by recrystallization using

Results and discussion

To improve the ecocompatibility of organic processes, among the several solvents were examined at variable temperature listed in Table 1 under catalyst free synthesis of tetrazole. Without any solvent, this reaction yielded to a lesser extent (Table 1, entry 1). A small rate of cycloaddition reaction goes on increase on changing the solvent from PEG-400 (Table 1, entry 5) to water (Table 1, entry 6) after a prolonged reaction time. With 50% aqueous glycerol (Table 1, entry 7) and 50%

Conclusion

To conclude, we have developed for the first time the use of glycerol in the synthesis of 5-substituted 1H-tetrazoles under catalyst free condition. This method is applicable for aryl nitriles, benzyl nitriles and also for sterically hindered nitriles. Short reaction time, good to excellent yields, safe process and simple workup make this method an attractive and useful contribution to the present methodologies.

Acknowledgments

We are grateful for the financial support from Department of Atomic Energy – Board of Research in Nuclear Sciences (DAE-BRNS) (No. 2009/37/39/BRNS/2268), Mumbai, India and North Maharashtra University, Jalgaon for providing necessary facilities.

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