Abstract
A simple and efficient protocol was developed for the synthesis of aryl azides directly from aryl carbinols using ZrCl4 as a Lewis acid catalyst. The azides were converted to novel triazoles under click reaction conditions, which were evaluated for their antimicrobial activity against various strains.
Highlights
Alcohol functionality, which is an attractive source of electrophile in view of green chemistry principles,[1a] is not a good leaving group
The direct displacement of an alcohol group with an azide group gains prominence, since the azide group is a direct source of amines, in addition to its stability and reactivity in click chemistry[6] and bioconjugation.[7]
The other C-N bond formation methods include, a two step conversion of alcohol to azide through mesylate,[10a] palladium catalyzed hydroazidation of homoallyl alcohols[10b] and gold catalyzed direct amination of benzhydryl alcohols.[10c]. In continuation of our interest on the catalytic applications of ZrCl4 as a Lewis acid for various organic transformations,[11] we disclose ZrCl4 catalyzed conversion of the known carbinols 1-5[12] (Scheme 1), into the corresponding azides 6-10, with TMSN3 in CH3CN at room temperature, click reaction of azides and biological evaluation of the derived 1,2,3-triazoles (6a -10d)
Summary
Alcohol functionality, which is an attractive source of electrophile in view of green chemistry principles,[1a] is not a good leaving group. The development of newer methods for direct conversion of a C-OH bond into a C-N bond, gains importance, since the amine group is very common in many natural products as well as pharmaceutically important compounds.[5] the direct displacement of an alcohol group with an azide group gains prominence, since the azide group is a direct source of amines, in addition to its stability and reactivity in click chemistry[6] and bioconjugation.[7] The most common method for the synthesis of azide is by the Mitsunobu displacement[8] with HN3 and its modifications.[9] The other C-N bond formation methods include, a two step conversion of alcohol to azide through mesylate,[10a] palladium catalyzed hydroazidation of homoallyl alcohols[10b] and gold catalyzed direct amination of benzhydryl alcohols.[10c] In continuation of our interest on the catalytic applications of ZrCl4 as a Lewis acid for various organic transformations,[11] we disclose ZrCl4 catalyzed conversion of the known carbinols 1-5[12] (Scheme 1), into the corresponding azides 6-10, with TMSN3 in CH3CN at room temperature, click reaction of azides and biological evaluation of the derived 1,2,3-triazoles (6a -10d)
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