Synthesis of some 5-aryl(hetaryl)tetrazoles by ultrasonication

Pusinov, G. L.; Ишметова, Р. И.; Kitaeva, V. G.; Beresnev, D. G.

doi:10.1007/bf01184883

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2000

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“…A longer reaction time or alternatively higher power input led to the formation of side products, and no improvement of the isolated yield was observed. On the other hand the microwave irradiation provided the electron rich tetrazole 3a from 2a in a better yield than previously reported …”

Section: Resultsmentioning

confidence: 48%

Fast Microwave-Assisted Preparation of Aryl and Vinyl Nitriles and the Corresponding Tetrazoles from Organo-halides

2000

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Aryl and vinyl nitriles have been prepared in very high yields from the corresponding bromides using palladium-catalyzed reactions with microwave irradiation employed as the energy source. Furthermore, flash heating was used successfully for the conversion of these nitriles into aryl and vinyl tetrazoles by cycloaddition reactions. One-pot transformation of aryl halides directly to the aryl tetrazoles could be accomplished both in solution and on solid support. All reactions were completed in minutes rather than in hours or days as previously reported with the standard thermal heating technique. A very potent HIV-1 protease inhibitor (K(i) = 0. 56 nM), comprising two tetrazole heterocycles as carboxyl group bioisosteres, was prepared in one pot by microwave-promoted cyanation of a bromo precursor and a subsequent cycloaddition reaction. The temperature-time profiles at 13, 20, and 60 W magnetron input power in DMF are presented.

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Section: Resultsmentioning

confidence: 48%