54347-27-2Relevant articles and documents
An efficient Passerini tetrazole reaction (PT-3CR)
Chandgude, Ajay L.,D?mling, Alexander
, p. 3718 - 3721 (2016)
A sonication accelerated, catalyst free, simple, high yielding and efficient method for the Passerini-type three-component reaction (PT-3CR) has been developed. It comprises the reaction of an aldehyde/ketone, an isocyanide and a TMS-azide in methanol:wat
Three-component reaction of ketals, isonitriles, and trimethylsilyl azide
Golantsov, Nikita E.,Nguyen, Hung M.,Varlamov, Aleksey V.,Aksenov, Aleksander V.,Voskressensky, Leonid G.
, p. 446 - 450 (2017)
[Figure not available: see fulltext.] It was demonstrated that a ZnCl2-catalyzed three-component reaction of ketals, isonitriles, and trimethylsilyl azide led to 1,5-disubstituted tetrazoles in moderate to high yields.
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.
, 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.
