25039-22-9Relevant academic research and scientific papers
Ruthenium-catalyzed enaminoketone formation from propargyl alcohols
Haak, Edgar
, p. 1847 - 1848 (2006)
Monomeric ruthenium(0) complexes containing electronically coupled dienone ligands were found to catalyze the formation of enaminoketones from propargyl alcohols. Georg Thieme Verlag Stuttgart.
A Method for the Preparation of β-Amino-α,β-unsaturated Carbonyl Compounds: Study of Solvent Effect and Mechanism
R. S., Reyno,Sugunan, Akash,S., Ranganayakulu,Suresh, Cherumuttathu H.,Rajendar, Goreti
supporting information, p. 1040 - 1045 (2020/02/15)
An efficient method for the preparation of β-amino-α,β-unsaturated carbonyl compounds is demonstrated. Bench-stable sodium 3-oxo-enolates were prepared from carbonyl compounds, and reacted with amines in the presence of an acid and a desiccant. DFT studie
Stereoselective synthesis of trifluoromethyl-substituted 2: H -furan-amines from enaminones
Liang, Xiaoyu,Guo, Pan,Yang, Wenjie,Li, Meng,Jiang, Chengzhou,Sun, Wangbin,Loh, Teck-Peng,Jiang, Yaojia
supporting information, p. 2043 - 2046 (2020/02/22)
A straightforward strategy for synthesis of highly functionalized trifluoromethyl 2H-furans is described. The copper catalyzed method relies on a cascade cyclic reaction between enaminones and N-tosylhydrazones. This method allows the synthesis of 2-amino
Highly Site-Selective Metal-Free C-H Acyloxylation of Stable Enamines
Wang, Fei,Sun, Wangbing,Wang, Yixin,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 1256 - 1260 (2018/02/23)
A highly site-selective acyloxylation of stable enamines with PhI(OAc)2 under metal-free conditions to afford (E)-vinyl acetate derivatives in good to excellent yields is described. Depending on the judicious choice of the solvent system, either the α- or β-site-selective product could be obtained with high selectivity. For the α-site-selective product, the rearranged amide compound is obtained as the major product. This reaction proceeds under mild reaction conditions (room temperature, metal-free, and open-flask) and features a broad substrate scope.
Synthesis of Polyaromatic Rings: Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization
Liang, Gaohui,Rong, Jiaxin,Sun, Wangbin,Chen, Gengjia,Jiang, Yaojia,Loh, Teck-Peng
supporting information, (2018/11/23)
An expedient [5 + 1] annulation method via Rh(III)-catalyzed C-H bond functionalization of enaminones to synthesize polyaromatic rings is described. The reaction tolerates a broad range of functional groups and offers a new entry to construct polycyclic a
Synthesis of Polyaromatic Rings: Rh(III)-Catalyzed [5 + 1] Annulation of Enaminones with Vinyl Esters through C-H Bond Functionalization
Liang, Gaohui,Rong, Jiaxin,Sun, Wangbin,Chen, Gengjia,Jiang, Yaojia,Loh, Teck-Peng
supporting information, p. 7326 - 7331 (2018/11/25)
An expedient [5 + 1] annulation method via Rh(III)-catalyzed C-H bond functionalization of enaminones to synthesize polyaromatic rings is described. The reaction tolerates a broad range of functional groups and offers a new entry to construct polycyclic a
Tunable and Diastereoselective Br?nsted Acid Catalyzed Synthesis of β-Enaminones
Kang, Ye-Won,Cho, Yu Jin,Han, Seung Jin,Jang, Hye-Young
supporting information, p. 272 - 275 (2016/02/03)
The Br?nsted acid catalyzed Meyer-Schuster reaction of hemiaminals was studied for the stereoselective synthesis of β-enaminones. Hemiaminals were formed from propargyl aldehydes (or the oxidation of propargyl alcohols) and amines in the presence of Br?ns
Highly regioselective synthesis of cis-β-enaminones by 1,4-addition of propiolaldehydes
Shi, Wenjuan,Sun, Shaofa,Wu, Minghu,Catano, Bryant,Li, Wan,Wang, Jian,Guo, Haibing,Xing, Yalan
supporting information, p. 468 - 471 (2015/04/27)
A convenient one-pot strategy for the regioselective synthesis of cis-β-enaminones has been developed via the condensation of propiolaldehydes and amines in EtOH. This process has opened a new synthetic route to enamines in good yield. A possible reaction mechanism involving a Michael addition/enol tautomerization via a six-membered ring transition state is proposed.
Synthesis of the naphthalenone, dihydroquinoline, and dihydrofuran derivatives
Guengoer, Fuesun Seyma,Anac, Olcay,Sezer, Oezkan
, p. 1115 - 1129 (2011/08/05)
The reactions of enaminones with dimethyl diazomalonate were investigated in the presence of copper(II) acetylacetonate. From the reaction of (E)-3-[methyl(phenyl)amino]-1-phenylprop-2-en-1-one (6c), dimethyl 2-[methyl(phenyl)amino]-4-oxonaphthalene-1,1-(4H)-dicarboxylate, was unexpectedly obtained as the major product. Quinoline derivatives were formed as the major products in the case of N-methyl-p-anisidino and N-methyl-p-toluidino enaminones. The reactions of acetyl enaminones were also realized, and quinoline derivatives were isolated as the major products. 3H- and 5H-dihydrofurans were also formed as side products in these reactions. These results differ from those reported earlier on the reactions of tertiary enaminones with carbenes/metal carbenes.
Ruthenium complexes of electronically coupled cyclopentadienone ligands - Catalysts for transformations of propargyl alcohols
Haak, Edgar
, p. 2815 - 2824 (2008/03/13)
A series of donor- and acceptor-substituted ruthenium cyclopentadienone complexes were synthesized and their catalytic activities towards propargyl alcohols focused on amination reactions have been investigated. It is shown that the substituents of the cyclopentadienone ligand determine the mode of activation of propargyl alcohols by these complexes leading to different central intermediates in catalytic cycles. Catalytic transformations of propargyl alcohols to α- or β-amino ketones, enamino ketones, α,β-unsaturated imines, ketones, alkenes and conjugated enynes could be achieved. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
