- Br?nsted Base-Catalyzed Formal Reductive [3+2] Annulation of 4,4,4-Trifluorocrotonate and α-Iminoketones
-
A formal reductive [3+2] annulation of 4,4,4-trifluorocrotonate and α-iminoketones was developed under Br?nsted base catalysis. A single phosphazene base efficiently catalyzes the one-pot tandem reaction involving two mechanistically different elementary processes, namely the chemoselective reduction of an imine moiety of α-iminoketones with thiols as the reductant and the subsequent intermolecular Michael addition of an enolate of α-aminoketones concomitant with lactam formation. This operationally simple method provides β-trifluoromethyl-substituted γ-lactams with a tetrasubstituted carbon as a single diastereomer.
- Kondoh, Azusa,Terada, Masahiro
-
p. 585 - 588
(2020/12/07)
-
- Catalyst-free facile and efficient one-pot synthesis of densely functionalized pyrroles and α-amino ketones
-
An efficient catalyst-free one-pot three-component synthesis of penta-substituted pyrroles has been successfully developed. A variety of penta-substituted pyrroles were straightforwardly synthesized from good to excellent yields (78%–93%) by using easily
- Vanga, Sivarama Krishna Reddy,Bollikolla, Hari Babu,Peruri, V. V. Satyanarayana
-
supporting information
p. 892 - 899
(2021/02/01)
-
- Visible-Light-Promoted Photocatalyst-Free Hydroacylation and Diacylation of Alkenes Tuned by NiCl2·DME
-
Herein, we describe a visible light-promoted hydroacylation strategy that facilitates the preparation of ketones from alkenes and 4-acyl-1,4-dihydropyridines via an acyl radical addition and hydrogen atom transfer pathway under photocatalyst-free conditions. The efficiency was highlighted by wide substrate scope, good to high yields, successful scale-up experiments, and expedient preparation of highly functionalized ketone derivatives. In addition, this protocol allows for the synthesis of 1,4-dicarbonyl compounds through alkene diacylation in the presence of NiCl2·DME.
- Zhao, Xinxin,Li, Bing,Xia, Wujiong
-
p. 1056 - 1061
(2020/02/15)
-
- Synthesis and lung cancer cell line study of pyrrolo[2,3-d]pyrimidine analogs
-
Three series of new pyrrolo[2,3-d]pyrimidines having diverse groups at position C4 and N7 of the pyrrolo[2,3-d]pyrimidine core were synthesized and their cell line study on the National Cancer Institute (NCI) H1 299 lung cancer cell line was performed. The details of the synthetic methods and characterization data of the synthesized compounds have been presented in this study. Compounds 08a, 08h, 08j, 09h, 09i, 09j, 09m, 09n, and 09o showed excellent anticancer activity compared to standard doxorubicin half maximal inhibitory concentration value on NCI H1 299 (lung cancer cell line) which was nontoxic to normal Vero cell line.
- Dholakia, Sandip P.,Kanada, Kaushik B.,Sureja, Dipen K.,Patel, Jitendra S.
-
p. 367 - 372
(2020/01/03)
-
- The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Bronsted Acids
-
An efficient method was developed for the synthesis of α-amino ketones from α-hydroxy imines. The reaction occurs through an α-iminol rearrangement involving the migration of a substituent of the carbinol carbon to the imine carbon. The optimal catalysts were found to be silica gel or montmorillonite K 10, which effected migration of a variety of aryl and alkyl substituents in high yields. The rearrangement can also be carried out on imines generated in situ from aldehydes and amines in essentially the same yields as those from the preformed imines.
- Zhang, Xin,Dai, Yijing,Wulff, William D.
-
p. 2015 - 2018
(2018/09/18)
-
- Selective synthesis of 1,4,5-trisubstituted imidazoles from α-imino ketones prepared by N-heterocyclic-carbene-catalyzed aroylation
-
An alternative synthetic route to 1,4,5-trisubstituted imidazoles from α-imino ketone, which can be prepared from imidoyl chlorides and aromatic aldehydes via N-heterocycle carbene-catalyzed aroylation was developed. This methodology consists of simple tr
- Takashima, Ryo,Tsunekawa, Kaoru,Shinozaki, Maki,Suzuki, Yumiko
-
p. 2261 - 2267
(2018/04/02)
-
- Coupling of Sulfoxonium Ylides with Arynes: A Direct Synthesis of Pro-Chiral Aryl Ketosulfoxonium Ylides and Its Application in the Preparation of α-Aryl Ketones
-
A general, mild, and versatile synthesis of the challenging α-aryl-β-ketosulfoxonium ylides has been developed for the first time, substituting traditional methods starting from diazo compounds. The arylation of easily accessible β-ketosulfoxonium ylides using aryne chemistry allowed the preparation of a large scope of the pro-chiral ylides in very good yields (40 examples; up to 85%). As applications, these ylides were smoothly converted into α-aryl ketones after desulfurization in good yields (up to 98%) as well as in other important derivatives.
- Talero, Alexánder Garay,Martins, Bruna Sim?es,Burtoloso, Antonio C. B.
-
p. 7206 - 7211
(2018/11/23)
-
- ORGANIC LUMINOGENS
-
Small molecule compounds having aggregation-induced emission (AIE) characteristics. The compounds include organic, aromatic salts having anion-π+ interactions. In some embodiments, the anion-π+ interactions can include heavy-atom-ani
- -
-
Page/Page column 38
(2018/12/14)
-
- A three-component one-pot synthesis of penta-substituted pyrroles via ring opening of α-nitroepoxides
-
A novel and facile one-pot reaction has been developed to synthesize a variety of penta-substituted pyrroles from α-nitroepoxides, primary amines and dialkyl acetylenedicarboxylates under the conditions without catalyst. Furthermore, the controlled experi
- Zhao, Donghong,Zhu, Yue,Guo, Shanshan,Chen, Wenteng,Zhang, Guolin,Yu, Yongping
-
supporting information
p. 2872 - 2877
(2017/04/26)
-
- Ionization and Anion-π+ Interaction: A New Strategy for Structural Design of Aggregation-Induced Emission Luminogens
-
Recent years have witnessed the significant role of anion-π+ interactions in many areas, which potentially brings the opportunity for the development of aggregation-induced emission (AIE) systems. Here, a new strategy that utilized anion-π
- Wang, Jianguo,Gu, Xinggui,Zhang, Pengfei,Huang, Xiaobo,Zheng, Xiaoyan,Chen, Ming,Feng, Haitao,Kwok, Ryan T. K.,Lam, Jacky W. Y.,Tang, Ben Zhong
-
supporting information
p. 16974 - 16979
(2017/11/30)
-
- Structure-activity relationship study and optimisation of 2-aminopyrrole-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile as a broad spectrum metallo-β-lactamase inhibitor
-
A SAR study on derivatives of 2-amino-1-benzyl-4,5-diphenyl-1H-pyrrole-3-carbonitrile 5a revealed that the 3-carbonitrile group, vicinal 4,5-diphenyl and N-benzyl side chains of the pyrrole are important for the inhibitory potencies of these compounds against members representing the three main subclasses of metallo-β-lactamases (MBLs), i.e. IMP-1 (representing the B1 subgroup), CphA (B2) and AIM-1 (B3). Coupling of 5a with a series of acyl chlorides and anhydrides led to the discovery of two N-acylamide derivatives, 10 and 11, as the two most potent IMP-1 inhibitors in this series. However, these compounds are less effective towards CphA and AIM-1. The N-benzoyl derivative of 5a retained potent in vitro activity against each of MBLs tested (with inhibition constants in the low μM range). Importantly, this compound also significantly enhanced the sensitivity of IMP-1, CphA- or AIM-1-producing cell cultures towards meropenem. This compound presents a promising starting point for the development of a universal MBL inhibitor, targeting members of each of the major subgroups of this family of enzymes.
- McGeary, Ross P.,Tan, Daniel T.C.,Selleck, Christopher,Monteiro Pedroso, Marcelo,Sidjabat, Hanna E.,Schenk, Gerhard
-
p. 351 - 364
(2017/06/19)
-
- SnCl2·2H2O-Catalyzed Solvent-Free Synthesis of α-Amino Ketones and Tetrasubstituted Pyrazines
-
Solvent-free reaction of various anilines with α-hydroxy ketones catalyzed by SnCl2·2H2O provides α-amino ketones in excellent yields. While a similar reaction with aliphatic amines is applicable for the synthesis of substituted pyrazines, SnCl2·2H2O permits versatility in the solvent-free reaction of α-hydroxy ketones with ammonium acetate to give the corresponding substituted pyrazines in good to excellent yields.
- Tamaddon, Fatemeh,Dehghani Tafti, Arefeh
-
p. 2217 - 2220
(2016/10/11)
-
- A new more atom-efficient multi-component approach to tetrasubstituted imidazoles: One-pot condensation of nitriles, amines and benzoin
-
A new more atom-efficient multi-component approach for the synthesis of tetrasubstituted imidazoles via the one-pot condensation of nitriles, primary amines and benzoin has been described. Using this method, a wide range of structurally diverse nitriles and primary amines were successfully condensed with benzoin in glycerol in the presence of TFA under microwave irradiation at 120 °C and all the products were obtained in good to excellent yields with higher atom efficiencies in comparison with the commonly used four-component condensation of aldehydes, ammonium acetate, primary amines and benzil.
- Khalafi-Nezhad, Ali,Shekouhy, Mohsen,Sharghi, Hashem,Aboonajmi, Jasem,Zare, Abdolkarim
-
p. 67281 - 67289
(2016/07/30)
-
- Alkyl halide-free heteroatom alkylation and epoxidation facilitated by a recyclable polymer-supported oxidant for the in-flow preparation of diazo compounds
-
Highly reactive metal carbenes, generated from simple ketones via diazo compounds, including diazoamides and -phosphonates, using a recyclable reagent inflow, are transient but versatile electrophiles for heteroatom alkylation reactions and for epoxide formation. The method produces no organic waste, with the only byproducts being water, KI and nitrogen, without the attendant hazards of isolation of intermediate diazo compounds.
- Nicolle, Simon M.,Hayes, Christopher J.,Moody, Christopher J.
-
supporting information
p. 4576 - 4579
(2015/03/18)
-
- Catalytic asymmetric α-iminol rearrangement: New chiral platforms
-
A series of 19 different asymmetric catalysts were screened in an effort to identify the first chiral catalyst for the rearrangement of α-hydroxy imines to α-amino ketones involving a 1,2-carbon shift. Although aluminate complexes of VAPOL, VANOL, and 7,7'-tBu2VANOL were quite effective catalysts giving up to 88% ee, the ne plus ultra catalyst for this reaction was found to be a zirconium complex of VANOL which gives 97 to >99% ee for the majority of the substrates examined. An X-ray diffraction study of the catalyst reveals that the zirconium exists as a homoleptic complex with three VANOL ligands and two protonated N-methyl imidazoles.
- Zhang, Xin,Staples, Richard J.,Rheingold, Arnold L,Wulff, William D.
-
p. 13971 - 13974
(2014/12/10)
-
- Titanium-mediated reductive cross-coupling reactions of imines with nitriles: An efficient route for the synthesis of α-aminoketones or 1,2-diketones
-
The reaction of imines with low-valent titanium species, generated in situ by using Ti(OiPr)4/2 c-C5H9MgCl reagent, affords titanium-imine complex, which can couple with nitriles to provide 2,5-diazatitanacyclop
- Chen, Haoyi,Fan, Guoqin,Li, Shi,Mao, Kebin,Liu, Yuanhong
-
supporting information
p. 1593 - 1596
(2014/03/21)
-
- Imidazole Derivatives Useful for Controlling Microbial Growth
-
Disclosure is provided for 1,4,5-substituted amino imidazole compounds useful to control microbial growth, compositions including these compounds, devices including these compounds, and methods of using the same.
- -
-
Paragraph 0160; 0161; 0162; 0163
(2013/07/19)
-
- Heteroannulation of arynes with N-aryl-α-aminoketones for the synthesis of unsymmetrical N-aryl-2,3-disubstituted indoles: An aryne twist of Bischler-Moehlau indole synthesis
-
Reaction of 2-(trimethylsilyl)aryl triflates 1 with N-aryl-α-amino ketones 2 afforded N-aryl-2,3-disubstituted indoles in good to excellent yields with complete control of the substitution patterns. This methodology allowed for the first time a one-step s
- Bunescu, Ala,Piemontesi, Cyril,Wang, Qian,Zhu, Jieping
-
supporting information
p. 10284 - 10286
(2013/10/22)
-
- A modular approach to the synthesis of 1,4,5-substituted-2-aminoimidazoles
-
Diversified 1,4,5-substituted-2-aminoimidazoles were rapidly assembled via sequential N-H insertion and Grignard addition to α-diazoesters. Lead compounds were identified as antibiotics against Gram-positive bacteria with an MIC value as low as 2 μg/mL.
- Su, Zhaoming,Peng, Lingling,Melander, Christian
-
p. 1204 - 1206
(2012/03/27)
-
- Highly stereoselective synthesis of β-amino ketones via a mannich reaction catalyzed by cellulose sulfuric acid as a biodegradable, efficient, and recyclable heterogeneous catalyst
-
The efficient use of cellulose sulfuric acid as a heterogeneous catalyst promotes three-component, one-pot Mannich reaction of various ketones, aromatic aldehydes, and aromatic amines in ethanol to make the corresponding β-amino ketones with high stereose
- Nemati, Firouzeh,Fakhaei, Amir Soheyl,Amoozadeh, Ali,Hayeniaz, Yaser Saeidi
-
experimental part
p. 3695 - 3702
(2011/10/09)
-
- Thiazolium-derived N-heterocyclic carbene-catalyzed cross-coupling of aldehydes with unactivated imines
-
Cross-coupling of aromatic aldehydes or benzoins with unactivated imines catalyzed by an N-heterocyclic carbene (NHC) affords α-amino ketones smoothly. The Royal Society of Chemistry.
- Li, Gong-Qiang,Dai, Li-Xin,You, Shu-Li
-
p. 852 - 854
(2007/10/03)
-
- Chemoselective reduction of α-imino carbonyl compounds into α-amino carbonyl compounds with titanium tetraiodide
-
α-Imino carbonyl compounds are chemoselectively reduced with titanium tetraiodide to give α-amino carbonyl compounds in good to excellent yields.
- Shimizu, Makoto,Sahara, Tetsuya,Hayakawa, Ryuuichirou
-
p. 792 - 793
(2007/10/03)
-
- Ruthenium clay catalyzed reduction of α-iminoesters and α-iminoketones, and the reductive amination of α-ketoesters
-
The reduction of α-iminoesters and α-iminoketones to the corresponding amino compounds was accomplished using ruthenium clay as the catalyst, at 75-100°C and 600-900 psi H2. The same catalyst proved efficient for the reductive amination of α-ketoesters (100°C, 600 psi H2). Diastereomeric excesses of up to 78% were obtained in the reductive amination reaction.
- Aldea, Raluca,Alper, Howard
-
p. 454 - 457
(2007/10/03)
-
- Synthesis and characterization of 9,10-bis(arylimino)-9,10-dihydrophenanthrenes, the structure of (Z,Z)-9,10-bis(phenylimino)-9,10-dihydrophenanthrene and PdCl2-[(E,E)-9,10-bis(phenylimino)-9,10-dihydrophenanthrene] in the solid state and in so
-
The synthesis and characterization of substituted phenanthrene-9,10-quinone diimines of the type 9,10-bis(arylimino)-9,10-dihydrophenanthrene (aryl-BIP) is described. These rigid bisnitrogen ligands have been synthesized by a metal-mediated cyclodehydroge
- Van Belzen, Ruud,Klein, Rene A.,Smeets, Wilberth J.J.,Spek, Anthony L.,Benedix, Roland,Elsevier, Cornelis J.
-
p. 275 - 285
(2007/10/03)
-
- Enamines et enediamines: synthese et oxydation anodique. Application a la formation de nouveaux heterocycles
-
The anodic oxidation of certain tertiary enamines and enediamines is particularly sensitive to the medium effect: specific action of bases leading to either dimers or trimers, or to the formation of a new 3 H-indole (case of enamines); reaction with moisture in the solvent allowing the obtention of indolooxazolidines (case of enediamines).The reactivity of the oxidized forms of the substrates is discussed as a function of the nature of the electrolysis medium and the structure of the products amenable to electrolysis.
- Cariou, Michel,Carlier, Roger,Simonet, Jacques
-
p. 781 - 792
(2007/10/02)
-
- Stereochemistry of Imino-group Reduction. Part 3. The Hydride Reduction of Achiral Benzil Monoimines
-
The RR,SS:RS,SR ratio of diastereoisomeric amino-alcohols obtained from the lithium aluminium hydride reduction of the monoimines prepared by reaction of benzil and various aliphatic and aromatic achiral amines has been determined.Stereochemical results a
- Alcaide, Benito,Lopez-Mardomingo, Carmen,Perez-Ossorio, Rafael,Plumet, Joaquin
-
p. 1649 - 1654
(2007/10/02)
-
- Metal Carbonyl Catalysis of Organoborane Reactions. Cobalt Carbonyl Catalyzed Reductive Carbonylation of Schiff Bases
-
Schiff bases react with trialkyl or triarylboranes and carbon monoxide, in the presence of catalytic amounts of cobalt carbonyl, to give amides.
- Alper, Howard,Amaratunga, Shiyamalie
-
p. 3593 - 3595
(2007/10/02)
-
- THE SELECTIVE REDUCTIVE ACYLATION OF α-KETO IMINES
-
Reaction of α-keto imines with the in situ generated acetylcobalt tetracarbonyl occurs only at the carbon-nitrogen double bond to give β-keto amides.An unexpected by-product was formed in several instances.
- Alper, Howard,Amaratunga, Shiyamaline
-
p. 3811 - 3812
(2007/10/02)
-
- Synthetic Uses of Open-Chain Analogues of Reissert Compounds
-
Open-chain analogues, 2, of Reissert compounds are readily obtained by reaction of cyanohydrins with primary amines, the resulting aminonitriles, 1, then being acylated.Hydrofluoroborate salts, 3, of 2 are prepared by reaction with fluoroboric acid in glacial acetic acid.The salts, 3, undergo 1,3-dipolar addition reactions with reactive alkynes to give substituted pyrroles and with ethyl acrylate to give a different type of substituted pyrrole, the initial step in this instance being a Diels-Alder reaction.The open-chain Reissert analogues 2 also undergo base-catalyzed reactions, such as alkylation to provide compounds 22, which, in turn, undergo cleavage reactions in ethanolic alkali to give ketones 23.A conjugate addition reaction of the anion 18 to methyl acrylate to give, after some subsequent steps, a substituted pyrrole, 9, has also been demonstrated. α-Anilino ketones 27 result when the anion 18 is caused to react with aldehydes, the initial reaction mixtures being subjected to subsequent alkaline hydrolysis.Finally, N-benzyl Reissert analogues have been found to give desoxybenzoins plus benzonitriles on treatment with sodium hydride in tetrahydrofuran.
- McEwen, William E.,Grossi, Anthony V.,MacDonald, Russell J.,Stamegna, Andrew P.
-
p. 1301 - 1308
(2007/10/02)
-