1607433-25-9Relevant academic research and scientific papers
Metal-free spirocyclization of N-arylpropiolamides with glyoxylic acids: Access to complex azaspiro-fused tricycles
Nair, Akshay M.,Shinde, Anand H.,Kumar, Shreemoyee,Volla, Chandra M.R.
, p. 12367 - 12370 (2020)
A metal-free oxidative cascade acylation and dearomatization of N-(p-methoxyaryl)propiolamides was achieved via K2S2O8 mediated decarboxylation of a-oxocarboxylic acids under operationally simple conditions to access azaspiro[4,5]-trienones in good to excellent yields. Furthermore, the utility of the protocol was illustrated in a one-pot reaction sequence consisting of Ugi-reaction/spirocyclization/ aza-Michael transformation for the construction of complex tricyclic cores having quaternary spirocenters.
Visible-Light-Mediated Nitrogen-Centered Radical Strategy: Preparation of 3-Acylated Spiro[4,5]trienones
Chen, Pu,Xie, Jun,Chen, Zan,Xiong, Bi-Quan,Liu, Yu,Yang, Chang-An,Tang, Ke-Wen
supporting information, p. 4440 - 4446 (2021/08/25)
A nitrogen-centered radical strategy for the preparation of 3-acylated spiro[4,5]trienones via visible-light-mediated acylation/ipso-cyclization of alkynes with acyl oxime esters is reported. The alkyl- and aryl-substituted acyl radicals, which generate from the cleavage of carbon-carbon σ-bonds in acyl oxime esters via nitrogen-centered radical pathway, attack the carbon-carbon triple bonds in propiolamides and then undergo ipso-cyclization. This method provides a way for the construction of 3-acyl-substituted spiro[4,5]trienones, which can introduce aryl- or alkyl-substituted acyl into spiro[4,5]trienone skeletons. (Figure presented.).
Visible-Light-Mediated Ipso-Carboacylation of Alkynes: Synthesis of 3-Acylspiro[4,5]trienones from N-(p-Methoxyaryl)propiolamides and Acyl Chlorides
Liu, Yu,Wang, Qiao-Lin,Zhou, Cong-Shan,Xiong, Bi-Quan,Zhang, Pan-Liang,Yang, Chang-An,Tang, Ke-Wen
, p. 2210 - 2218 (2018/02/23)
A novel visible-light-mediated ipso-carboacylation of N-(p-methoxyaryl)propiolamides with acyl chloride has been established for the synthesis of diverse 3-acylspiro[4,5]trienones with high selectivity and efficiency. This method represents a new difunctionalization of alkynes through cross coupling of the acyl chloride C-Cl bonds with an ipso-aromatic carbon by simultaneously forming two new carbon-carbon bonds and one carbon-oxygen double bond.
Metal-free oxidative ipso-carboacylation of alkynes: Synthesis of 3-acylspiro[4,5]trienones from N-arylpropiolamides and aldehydes
Ouyang, Xuan-Hui,Song, Ren-Jie,Li, Yang,Liu, Bang,Li, Jin-Heng
, p. 4582 - 4589 (2014/06/09)
A general and metal-free radical route to synthesis of 3-acylspiro[4,5] trienones is established that utilizes TBHP (tert-butyl hydrogenperoxide) as an oxidation and a reaction partner to trigger the oxidative ipso-carboacylation of N-arylpropiolamides with aldehydes. This method offers a new difunctionalization of alkynes through oxidative cross coupling of the aldehyde C(sp2)-H bond with an ipso-aromatic carbon.
