1620975-05-4Relevant academic research and scientific papers
TMSCl-mediated synthesis of α,β-unsaturated amides via C-C bond cleavage and C-N bond formation of propargyl alcohols with trimethylsilyl azide
Song, Xian-Rong,Song, Bo,Qiu, Yi-Feng,Han, Ya-Ping,Qiu, Zi-Hang,Hao, Xin-Hua,Liu, Xue-Yuan,Liang, Yong-Min
, p. 7616 - 7625 (2014)
A new method with high efficiency for the synthesis of α,β- unsaturated amides from the easily prepared propargyl alcohols and TMSN 3 using TMSCl as an acid promoter is developed. A wide variety of α,β-unsaturated amides were produced in moderate to excellent yields. Mechanistic studies indicate that this transformation involves TMSCl-mediated allenylazide intermediate formation, C-C bond cleavage, and C-N bond formation. Significantly, this reaction shows good functional group compatibility and high regioselectivity, with a relatively short reaction time and inexpensive reagents.
Transition-Metal-Free, Br?nsted Acid-Mediated Cascade Sequence in the Reaction of Propargyl Alcohols with Sulfonamido-indoles/-indolines: Highly Substituted δ- And α-Carbolines
Selvaraj, Karuppu,Swamy, K. C. Kumara
supporting information, p. 15043 - 15056 (2019/01/04)
Br?nsted acid-mediated, transition-metal-free reaction of propargyl alcohols with sulfonamido-indoles/-indolines under mild conditions affords highly substituted δ- or α-carbolines in good to excellent yields. This protocol involves cascade reaction seque
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
Song, Xian-Rong,Han, Ya-Ping,Qiu, Yi-Feng,Qiu, Zi-Hang,Liu, Xue-Yuan,Xu, Peng-Fei,Liang, Yong-Min
supporting information, p. 12046 - 12050 (2015/03/31)
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%).
