21759-74-0Relevant articles and documents
Carbonylation of silylated hydroxymethyl aziridines to β-lactams
Davoli, Paolo,Moretti, Irene,Prati, Fabio,Alper, Howard
, p. 518 - 521 (1999)
Functionalized β-lactams are synthesized by carbonylative ring expansion of silylated hydroxymethyl aziridines catalyzed by dicobalt octacarbonyl, a process that proceeds with inversion of configuration. Ring opening and elimination occurs on attempted carbonylation of aziridine carboxylates.
Tandem Nenitzescu Reaction/Nucleophilic Aromatic Substitution to Form Novel Pyrido Fused Indole Frameworks
Bhatia, Harshita,Debroye, Elke,Dehaen, Wim,Dey, Swapan,Prakash, Prabhat,Singh, Rashmi
, p. 4865 - 4875 (2021/09/22)
5-Hydroxyindoles are privileged structures that form part of various bioactive compounds. The Nenitzescu reaction of quinones and enamines is one of the most powerful methods to obtain 5-hydroxyindoles. In this work, we have applied the Nenitzescu reaction to 2-(2-chloropyrid-3-yl)benzoquinones. Mixtures of regioisomers were obtained that could be separated in the 4- and 6-substituted analogues, and then cyclized separately in a metal-free base-catalyzed reaction, affording novel tetracyclic indole derivatives. These are indeed the first examples reported in the literature of the linear pyrido[3′,2′ : 4,5]furo[3,2-b]indole and angular 1H-pyrido[2′,3′ : 4,5]furo[2,3-c]indole systems. The regioselectivity and the yield of the Nenitzescu reaction were found to be dependent on the N-substituent at the enamine. Furthermore, we analyzed the UV-Vis and PL spectra of the new systems, and this was supported by DFT calculations, allowing us to compare the properties of angular compared to linearly shaped compounds.
Highly efficient and facile synthesis of β-enaminones catalyzed by diphenylammonium triflate
Zhao, Ting-Ting,Song, Jiang-Long,Hong, Feng-Qing,Xia, Jian-Sheng,Li, Jian-Jun
, p. 2857 - 2868 (2019/08/21)
Abstract: The catalytic performance of diphenylammonium triflates as an organocatalyst in the synthesis of β-enaminones from various substituted β-diketones and amides (or amines) were evaluated. A wide range of β-enaminones were efficiently synthesized in good to excellent yields under mild reaction conditions. Applying diphenylammonium triflate (DPAT) as catalyst makes this protocol cost-effective, low corrosive and easy to handle. Graphic abstract: [Figure not available: see fulltext.].
Redox Property of Enamines
Li, Yao,Wang, Dehong,Zhang, Long,Luo, Sanzhong
, p. 12071 - 12090 (2019/10/11)
Enamines are electron-rich compounds bearing intriguing redox properties. Herein, a series of secondary enamines condensed from primary amine and β-ketocarbonyls were synthesized and their electrochemical oxidation properties were systematically studied by cyclic voltammetry. Furthermore, theoretical calculation of oxidation potentials of enamines, particularly those catalytic intermediates, was also conducted to further broaden the scope investigated. Possible structural factors on oxidation and the nature of the resulted radical cation intermediates were revealed and discussed. Correlation of redox potentials with molecular properties such as highest occupied molecular orbital energies and natural population analysis charge were explored, and there appears no simple linear correlation. On the other hand, a good correlation with Mayr's nucleophilicity parameter N was noted among a range of catalytically relevant enamines. Spin population analysis disclosed that enamine radical cations mainly exhibit the carbon-center free radical feature. Taking experimental and computation data together, a comprehensive picture about the redox property of enamines is presented, which would provide guidance in the development of oxidative enamine catalysis and transformations.
Transformation of One-Dimensional Achiral Structure to Three-Dimensional Chiral Structure: Mechanistic Study and Catalytic Activities of Chiral Structure
Rao, Purna Chandra,Chaudhary, Sonu Pratap,Kuznetsov, Denis,Mandal, Sukhendu
supporting information, p. 12669 - 12674 (2016/12/26)
We have isolated two copper-based coordination polymers through solvent diffusion and solvothermal methods using copper salt, furan dicarboxylic acid (FDC), 4,4′-bipyridine (bpy) in MeOH/ethylene glycol, and water solvents. Compound 1 is adopting P21/c space group and adopts a one-dimensional wirelike structure with a free carboxylate anion. Compound 2 crystallizes in chiral space group P65. This is a three-dimensional structure with helical chains. This helicity might be the reason for chiral generation and symmetry breaking. We have converted compound 1 to compound 2 using grinding, followed by a solvothermal method. The circular dichroism data of 2 showed that it is an enantioenriched compound. We have shown that compound 2 is a very good catalyst for chemo- and regioselective enamination reaction and for azide-alkyne Huisgen cycloaddition, respectively.
Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate
Feng, Cheng-Liang,Chu, Ning-Ning,Zhang, Shu-Guang,Cai, Jin,Chen, Jun-Qing,Hu, Hua-You,Ji, Min
, p. 1097 - 1103 (2014/05/20)
A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a "green synthesis", which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short reaction periods, lower loading of catalyst and chemo- and regio-selectivity. In addition, the catalyst was easily recovered from the reaction system and readily reused with minimal loss of activity.
Zn[aminoacid]2 hybrid materials applied as heterogeneous catalysts in the synthesis of β-enaminones
Winck, Cristiane R.,Darbem, Mariana P.,Gomes, Roberto S.,Rinaldi, Andrelson W.,Domingues, Nelson Luís C.
supporting information, p. 4123 - 4125 (2014/07/22)
Hybrid materials have seized attention from scientific community mainly as heterogenic catalysts in organic reactions on a large scale succeeding in some organic compounds with high yields. One of the most important classes of hybrid materials used for this purpose involves the complexation of Zn and aminoacids. Herein, we introduced Zn[Pro]2 and Zn[Gly]2 in the synthesis of several β-enaminones via solvent free protocol and using an ultrasound device.
Zn[aminoacid]2 hybrid materials applied as heterogeneous catalysts in the synthesis of β-enaminones
Winck, Cristiane R.,Darbem, Mariana P.,Gomes, Roberto S.,Rinaldi, Andrelson W.,Domingues, Nelson Luís C.
supporting information, p. 4123 - 4125 (2015/02/02)
Hybrid materials have seized attention from scientific community mainly as heterogenic catalysts in organic reactions on a large scale succeeding in some organic compounds with high yields. One of the most important classes of hybrid materials used for this purpose involves the complexation of Zn and aminoacids. Herein, we introduced Zn[Pro]2 and Zn[Gly]2 in the synthesis of several β-enaminones via solvent free protocol and using an ultrasound device.
A chemoselective route to β-enamino esters and thioesters
Xin, Dongyue,Burgess, Kevin
supporting information, p. 2108 - 2110 (2014/05/06)
Conditions were developed for syntheses of β-enamino esters, thioesters, and amides. These reactions involve hydroxybenzotriazole derivatives in buffered media. Illustrative syntheses of some heterocyclic systems are given, including some related to protein-protein interface mimics.
A study on the regioselectivity in N,C-acylation of β-enamino-esters
Defant, Andrea,Mancini, Ines
, p. 4586 - 4590 (2013/06/26)
With the aim to produce the new corresponding amide, amino pyrone 1 [=4-(benzylamino)-6-methyl-2H-pyran-2-one] was acylated in dichloromethane in the presence of triethylamine, obtaining an unexpected mixture of N- and C-acyl products in a 60:40 ratio, respectively. The regioselective investigation was enlarged by using a series of organic bases and taking into account both solvent effects and acyl halide structure. Conditions able to give pure amides or pure C-acyl products were established. The study also includes the reactivity of a β-enamino-ester with NH group involved in an intramolecular hydrogen bond, where pure C-acyl products were obtained.
