120869-85-4Relevant articles and documents
Some practical methods for the application of 5-metallo-1-benzyl-1H- tetrazoles in synthesis
Wiedemann, Sean H.,Bio, Matthew M.,Brown, Liane M.,Hansen, Karl B.,Langille, Neil F.
supporting information, p. 2231 - 2236 (2012/11/13)
Nucleophilic reagents such as 5-lithiotetrazoles are synthetically powerful tools for the installation of tetrazole functional groups, but they are of limited utility due to the instability of tetrazole-derived carbanions. Herein, we report practical methods for the generation and use of new 5-metallo-1-benzyl-1H-tetrazoles (M=K, MgX, ZnX) derived from either 1-benzyl-1H-tetrazole or 1-benzyl-5-bromo-1H-tetrazole. By varying the metal counterion, the tetrazole carbanion stability was improved. Potassium- and magnesium-derived reagents underwent additions to carbonyl compounds at -30 and -20°C, respectively. The isolated yields (41-85%) from these and other reactions were comparable to those reported for 5-lithiotetrazoles at much lower temperatures (-78 to -98 °C). Georg Thieme Verlag Stuttgart ? New York.
A click chemistry approach to tetrazoles by huisgen 1,3-dipolar cycloaddition: Synthesis of 5-acyltetrazoles from azides and acyl cyanides
Demko, Zachary P.,Sharpless, K. Barry
, p. 2113 - 2116 (2007/10/03)
Click chemistry: Acyl cyanides react with alkyl azides in high yield by heating at 120-130°C (see scheme). The reactions are run neat, and the workup is simple. When p-nitrophenyl cyanoformate is used as the dipolarophile, the resulting tetrazoles are act
