55779-43-6Relevant academic research and scientific papers
Achieving Aliphatic Amine Addition to Arylalkynes via the Lewis Acid Assisted Triazole-Gold (TA-Au) Catalyst System
Jia, Teng,Fan, Shengyu,Li, Fengmian,Ye, Xiaohan,Zhang, Wenke,Song, Zhiguang,Shi, Xiaodong
supporting information, p. 6019 - 6023 (2021/08/03)
Transition metal catalyzed intermolecular hydroamination of the arylalkynes with aliphatic amine is generally problematic due to the good coordination between amine and metal cation. With the combination of 1,2,3-triazole coordinated gold(I) catalyst (TA-Au) and Zn(OTf)2 cocatalyst, this challenging transformation was achieved with good to excellent yields and regioselectivity. Compared to previously reported methods, this approach offered an alternative catalyst system to achieve this fundamental chemical transformation with high efficiency and practical conditions.
Synthesis of β-arylacyl / β-heteroarylacyl-β-alkylidene malonates and their application in substituted pyridone synthesis
Wagh, Manoj Balu,Shankar,Mini,Krishnamohan,Madhubabu,Pal, Abir K.,Jayaprakash, Sarva,Krishna,Dahanukar, Vilas,Kumar, U. K. Syam,Gill
, p. 49 - 55 (2013/04/23)
A novel approach has been developed for the synthesis of β-arylacyl/β-heteroarylacyl-β-alkylidine malonates in moderate to good yields by the reaction of Stork aryl and heteroaryl enamine with β-chloroalkylidene malonates. The reaction involves conjugate
New reaction of enamines with aryldiazoacetates catalyzed by transition metal complexes
Zhao, Wei-Jie,Yan, Ming,Huang, Dan,Ji, Shun-Jun
, p. 5585 - 5593 (2007/10/03)
The reaction of aryldiazoacetates with enamines catalyzed by copper and rhodium complexes provided γ-keto esters in good yields. A full investigation of the effects of solvents, catalysts, enamines and aryldiazoacetates on the reaction was carried out. Careful analysis of the crude reaction mixture revealed a substituted enamine as the primary product, which was hydrolyzed over silica gel to give a γ-keto ester as the final product. A reaction mechanism involving nucleophilic addition of an enamine to a metal carbene and subsequent hydrogen transfer was proposed. Chiral dirhodium and copper catalysts were examined and found to provide γ-keto esters with no enantioselectivity. The result could be rationalized based on the proposed reaction mechanism. Attempts to trap the enamine intermediate with several electrophilic reagents were not successful.
Chemistry of Free Cyclic Vicinal Tricarbonyl Compounds ('1,2,3-Triones'). Part 3. Polar and Redox Reactions of 1,2,3-Triones with Enamines of Different Types - News on Oxonol Dyes, Radicals, and Biradicals
Schank, Kurt,Lieder, Robert,Lick, Carlo,Glock, Rebecca
, p. 869 - 924 (2007/10/03)
The central C=O groups of cyclic 1,2,3-triones possess outstanding electrophilic (electron-pair-accepting) as well as oxidizing (one-electron-accepting) properties. Thus, 1,2,3-triones are chemically related to 1,2- and 1,4-benzoquinones. Whereas polar reactions with carbanion-like (electron rich) species give rise to nucleophilic addition reactions to C=O groups under exclusive C,C-bond formation, SET (single-electron transfer) or redox reactions effect a partial 'carbonyl Umpolung' via ketyl intermediates (C,C- and/or C,O-bond formation). Here, we report on numerous reactions between electron-rich, more- or less-polar enamines with 5,5-dimethylcyclohexane-1,2,3-trione (9a) and 1H-indene-1,2,3-trione (9b). Various new derivatives of basic oxonol dyes were formed, including the first oxonol dye incorporating a 1,3-dioxocyclohexyl moiety. A novel stable radical, 50/50′, was obtained from 9b and lla via addition, hydrolysis, and treatment with conc. H2SO4. Radical 50/50′ represents a vinylogous 'monodehydroreductone' and is, thus, related to monodehydroascorbic acid (143), to Russell's radical cation (144), to indigo (141/141′), and to quinhydrone.
