n‐Butyllithium‐mediated reactions of 1‐(2‐azidoarylmethyl)‐ 1H‐benzotriazoles with alkyl halides

Abstract

Treatment of 1‐(2‐azidoarylmethyl)‐1H‐benzotriazoles (6) with n‐BuLi (2.5 equiv.) in THF at −78°C, followed by an addition of alkyl halides such as allyl, benzyl, and ethyl bromides with stirring for 2 h at room temperature afforded 2‐(dialkylamino)‐3‐(benzotriazol‐1‐yl)‐2H‐indazoles (8), 3‐(benzotriazol‐ 1‐yl)‐2H‐indazoles (9), 2‐[(benzotriazol‐1‐yl)methyl]arylamine (10), and 2‐[(benzotriazol‐1‐yl)(alkyl) methyl]arylamine (11). J. Heterocyclic Chem., 2010.

Synthesis of substituted triazole–pyrazole hybrids using triazenylpyrazole precursors

“…These are usually accessed from the respective amines or organohalides (5 and 6, Scheme 1) [14,[16][17][18]. Few examples of triazole-pyrazole hybrids, such as 13, have also been synthesized through a modified Sakai reaction [19], a reaction cascade involving the elimination of an azole [20] or in the n-butyllithium-mediated reaction with alkyl halides [21]. So far, the literature-reported methods are most often limited to N-unsubstituted pyrazoles or triazoles and pyrazoles being fused to a second (hetero)cycle; the synthesis of promising multi-substituted structures such as 1 has not yet been described systematically.…”

Design, Synthesis, Characterization, and Antimicrobial Screening of Novel Indazole Bearing Oxadiazole Derivatives

“…Cortivazol is an indazole‐based drug possessing glucocorticoid properties. Many indazoles act as enzyme inhibitors , and some also show specific virucide , bronchodilatory , vasodilatory , or neuroprotectant activities; others are used in the treatment of diabetes . 3‐Trifluoromethyl‐1 H ‐indazoles possess trichomonacide properties , and fused indazoles with an azasteroid ring system show antimicrobial activity .…”