1197-51-9Relevant articles and documents
Synthesis of multiply substituted 1,6-dihydropyridines through Cu(I)-catalyzed 6-endo cyclization
Mizoguchi, Haruki,Watanabe, Ryo,Minami, Shintaro,Oikawa, Hideaki,Oguri, Hiroki
, p. 5955 - 5963 (2015)
Copper-catalyzed 6-endo cyclization of N-propargylic β-enaminocarbonyls was developed for the synthesis of oxidation-labile 1,6-dihydropyridines. This synthetic method allows flexible and regio-defined assembly of various substituents at the N1, C2, C3, C4, and C6 positions of 1,6-dihydropyridines under mild conditions.
-
Sinda et al.
, p. 331 (1973)
-
The regiochemistry of carbenoid insertion into zirconacycles
Gordon, George J.,Luker, Tim,Tuckett, Mark W.,Whitby, Richard J.
, p. 2113 - 2129 (2000)
The regioselectivity of insertion of lithium chloroallylides (allyl carbenoids) into a wide variety of unsymmetrical zirconacycles has been determined. In all but one case a single regioisomer was obtained. A combination of steric and electronic effects is needed to explain the results and imply that the carbenoid is acting predominantly as an electrophilic species. The first carbenoid insertion into a zirconacyclopentadiene is noted. (C) 2000 Elsevier Science Ltd.
Highly regioselective synthesis of substituted isoindolinones via ruthenium-catalyzed alkyne cyclotrimerizations
Foster, Robert W.,Tame, Christopher J.,Hailes, Helen C.,Sheppard, Tom D.
, p. 2353 - 2360 (2013)
(Cyclooctadiene)(pentamethylcyclopentadiene) ruthenium chloride [Cp*RuCl (cod)] has been used to catalyze the regioselective cyclization of amide-tethered diynes with monosubstituted alkynes to give polysubstituted isoindolinones. Notably, the presence of a trimethylsilyl group on the diyne generally led to complete control over the regioselectivity of the alkyne cyclotrimerization. The cyclization reaction worked well in a sustainable non-chlorinated solvent and was tolerant of moisture. The optimized conditions were effective with a diverse range of alkynes and diynes. The 7-silylisoindolinone products could be halogenated, protodesilylated or ring opened to access a range of usefully functionalized products.
Synthesis of polysubstituted pyrroles from activated alkynes and n-propargylamines through base-catalyzed cascade reaction
Weng, Jianquan,Chen, Yong,Yue, Binjie,Xu, Meng,Jin, Hongwei
, p. 3164 - 3170 (2015)
A novel K3PO4-catalyzed synthesis of polysubstituted pyrroles by a Michael addition/alkyne carbocyclization of activated alkynes and N-propargylamines has been developed. This transition-metal-free cascade process represents an environmental friendly and efficient way to construct polysubstituted pyrroles in good yields. Catalyzed by CsF, a Michael addition/aza-Claisen rearrangement/cyclization sequential process has been achieved to selectively synthesize pyrroles in moderate yields. An efficient method for the synthesis of polysubstituted pyrroles from activated alkynes and N-propargylamines has been developed. This cascade process represents an atom- and step-economical way to construct a range of polysubstituted pyrroles and involves base-catalyzed Michael addition/alkyne carbocyclization or Michael addition/aza-Claisen rearrangement/cyclization.
N-Propargylamine-hydroxypyridinone hybrids as multitarget agents for the treatment of Alzheimer's disease
Bai, Renren,Ge, Jiamin,Guo, Jianan,Jiang, Xiaoying,Xie, Yuanyuan,Yao, Chuansheng,Zhang, Changjun,Zhang, Jingqi,Zhang, Yujia,Zhong, Zhichao,Zhou, Tao
, (2021/06/07)
AD is a progressive brain disorder. Because of the lack of remarkable single-target drugs against neurodegenerative disorders, the multitarget-directed ligand strategy has received attention as a promising therapeutic approach. Herein, we rationally designed twenty-nine hybrids of N-propargylamine-hydroxypyridinone. The designed hybrids possessed excellent iron-chelating activity (pFe3+ = 17.09–22.02) and potent monoamine oxidase B inhibitory effects. Various biological evaluations of the optimal compound 6b were performed step by step, including inhibition screening of monoamine oxidase (hMAO-B IC50 = 0.083 ± 0.001 μM, hMAO-A IC50 = 6.11 ± 0.08 μM; SI = 73.5), prediction of blood–brain barrier permeability and mouse behavioral research. All of these favorable results proved that the N-propargylamine-hydroxypyridinone scaffold is a promising structure for the discovery of multitargeted ligands for AD therapy.
One-pot, two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazoles
Kuang, Lu,Ming, Peng,Wan, Chang-Feng,Chen, Jun-Min,Sheng, Shou-Ri
, p. 563 - 569 (2020/11/19)
A facile, one-pot two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazole derivatives has been developed. The protocol employs an N-allylation of N-propargylated amines with 2,3-dibromopropene in the presence of K2CO3 in DMSO and a CuI-catalyzed [3 + 2] cycloaddition reaction of the synthetic N-(2-bromoallyl)-N-propargyl amines with sodium azide sequentially. Such a method provides methylene-substituted 1,2,3-triazole fused piperazines with some advantages such as simple operation, high efficiency and good product yield (80–91%) through readily available starting materials.