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- Title
Lewis Acid Mediated Tandem Reaction of Propargylic Alcohols to Tetrazoles Involving C--O- and C--C-Bond Cleavage Reactions and a C--N-Bond Formation.
- Authors
Song, Xian‐Rong; Han, Ya‐Ping; Qiu, Yi‐Feng; Qiu, Zi‐Hang; Liu, Xue‐Yuan; Xu, Peng‐Fei; Liang, Yong‐Min
- Abstract
A novel and direct synthesis of 1-aryl-5-arylvinyltetrazoles from easily prepared propargylic alcohols and TMSN3 is developed in the presence of TMSCl under mild conditions (TMS=trimethylsilyl). The process involves an allenylazide intermediate, followed by a C--C-bond cleavage and C-N-bond formation to afford the desired products. Moreover, this method offers a good functionalgroup applicability and can be scaled-up to grams (yield up to 85 %).
- Subjects
LEWIS acids; FUNCTIONAL groups; ORGANIC chemistry; TETRAZOLES; CARBON-carbon bonds; CHEMICAL synthesis
- Publication
Chemistry - A European Journal, 2014, Vol 20, Issue 38, p12046
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201403752