- The Acceleration of the Rearrangement of α-Hydroxy Aldimines by Lewis or Bronsted Acids
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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.
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- 2-(4-chloroanilino)- and 2-(4-methoxyanilino)-1,2-diphenylethanone
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The title compounds, C20H16ClNO and C 21H19NO2, adopt syn orientations of the C=O and N - H bonds but, like their analogues, form no strong intermolecular hydrogen bonds.
- Batsanov, Andrei S.,Goeta, Andres E.,Howard, Judith A.K.,Soto, Bernardino,Au-Alvarez, Oscar
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- Chemoselective reduction of α-imino carbonyl compounds into α-amino carbonyl compounds with titanium tetraiodide
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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
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- Catalytic Diastereo- and Enantioconvergent Synthesis of Vicinal Diamines from Diols through Borrowing Hydrogen
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We present herein an unprecedented diastereoconvergent synthesis of vicinal diamines from diols through an economical, redox-neutral process. Under cooperative ruthenium and Lewis acid catalysis, readily available anilines and 1,2-diols (as a mixture of diastereomers) couple to forge two C?N bonds in an efficient and diastereoselective fashion. By identifying an effective chiral iridium/phosphoric acid co-catalyzed procedure, the first enantioconvergent double amination of racemic 1,2-diols has also been achieved, resulting in a practical access to highly valuable enantioenriched vicinal diamines.
- Feng, Wei,Gao, Taotao,Lau, Kai Kiat,Lin, Yamei,Pan, Hui-Jie,Yang, Binmiao,Zhao, Yu
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supporting information
p. 18599 - 18604
(2021/08/09)
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- Visible-Light-Induced Radical Acylation of Imines with α-Ketoacids Enabled by Electron-Donor-Acceptor Complexes
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A visible-light-induced radical acylation of imines with α-ketoacids has been achieved, enabled by an electron-donor-acceptor (EDA) complex. This EDA complex-mediated process eradicates the use of a photocatalyst. Visible light is used as the sole promote
- Zhang, Hong-Hao,Yu, Shouyun
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p. 3711 - 3715
(2019/05/24)
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- Synthesis and lung cancer cell line study of pyrrolo[2,3-d]pyrimidine analogs
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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.
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p. 367 - 372
(2020/01/03)
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- ORGANIC LUMINOGENS
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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
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Page/Page column 40
(2018/12/14)
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- Br?nsted Base-Catalyzed Reductive Cyclization of Alkynyl α-Iminoesters through Auto-Tandem Catalysis
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A novel reductive cyclization of alkynyl α-iminoesters was developed through auto-tandem catalysis with a Br?nsted base as the catalyst. The reaction system involves two mechanistically different elementary processes, both of which are efficiently catalyz
- Kondoh, Azusa,Terada, Masahiro
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supporting information
p. 5309 - 5313
(2018/09/13)
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- Novel antiviral compounds against gastroenteric viral infections
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Viral gastroenteritis is a serious viral infection which affects a large number of individuals around the world, most of them being children. The infection may occur due to different viruses, for example, coxsackievirus, adenovirus, and rotavirus. There i
- Mohamed, Mosaad S.,El-Hameed, Rania H. Abd,Sayed, Amira I.,Soror, Sameh H.
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p. 194 - 205
(2015/03/14)
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- Titanium-mediated reductive cross-coupling reactions of imines with nitriles: An efficient route for the synthesis of α-aminoketones or 1,2-diketones
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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
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supporting information
p. 1593 - 1596
(2014/03/21)
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- Synthesis of chiral NADH analog based on proline template including thiourea and nicotinic acid moieties
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Chiral reductase-mimicking organic molecule built on proline template incorporating a covalently bound NADH mimic via thiourea, and related reducing agent Hantzsch dihydropyridine, was designed. A synthetic path was developed involving interlinking of chiral proline derivatives with thiourea and subsequent coupling reaction with nicotinoyl chloride. The structure of target compound was studied by x-ray, indicating a double H bond with thiourea hydrogens and oxygen O1 of benzylcarbamate fragment. The reduction of benzil and imines was performed. Taylor & Francis Group, LLC.
- Bagdziunas, Gintautas,Haukka, Matti,Butkus, Eugenijus
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experimental part
p. 2517 - 2523
(2011/08/07)
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- 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
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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.
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p. 275 - 285
(2007/10/03)
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- Stereochemistry of Imino-group Reduction. Part 3. The Hydride Reduction of Achiral Benzil Monoimines
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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
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p. 1649 - 1654
(2007/10/02)
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- Metal Carbonyl Catalysis of Organoborane Reactions. Cobalt Carbonyl Catalyzed Reductive Carbonylation of Schiff Bases
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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
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p. 3593 - 3595
(2007/10/02)
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- THE SELECTIVE REDUCTIVE ACYLATION OF α-KETO IMINES
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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
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p. 3811 - 3812
(2007/10/02)
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