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.
abstract: A novel and direct synthesis of 1-aryl-5-arylvinyl-tetrazoles 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 functional-group applicability and can be scaled-up to grams (yield up to 85 %).
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou 730000 (China), Fax: (+86) 931-891-2582.
authors.forename: Xian-Rong
authors.initials: XR
authors.lastname: Song
authors.forename: Ya-Ping
authors.initials: YP
authors.lastname: Han
authors.forename: Yi-Feng
authors.initials: YF
authors.lastname: Qiu
authors.forename: Zi-Hang
authors.initials: ZH
authors.lastname: Qiu
authors.forename: Xue-Yuan
authors.initials: XY
authors.lastname: Liu
authors.forename: Peng-Fei
authors.initials: PF
authors.lastname: Xu
authors.forename: Yong-Min
authors.initials: YM
authors.lastname: Liang
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000480:Alkynes / Q000737:chemistry*; D002384:Catalysis; D058116:Lewis Acids / Q000737:chemistry*; D015394:Molecular Structure; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism; D013777:Tetrazoles / Q000737:chemistry*
chemical_list: D000438:Alcohols; D000480:Alkynes; D058116:Lewis Acids; D020005:Propanols; D013777:Tetrazoles; C028255:propargyl alcohol
keywords: 1-aryl-5-arylvinyl-tetrazoles; CC-bond cleavage; CN-bond formation; Lewis acids; propargylic alcohols