- S,S-Complexes of Copper(I) Halides with 1,2-Bis(3,5-dimethyloxazol-4-ylmethylsulfanyl)ethane as New Catalysts for Phenylacetylene Aminomethylation
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New metal–heterocycle S,S-complexes based on Cu(I) binary halides and a polydentate ligand, 1,2- bis(3,5-dimethyloxazol-4-ylmethylsulfanyl)ethane have been prepared. The obtained complexes have demonstrated high catalytic activity in aminomethylation of p
- Akhmetova,Akhmadiev,Nurtdinova,Yanybin,Glazyrin,Ibragimov
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- SYNTHESIS OF AZONIA DERIVATIVE OF HEXAHELICINE
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The azonia derivative of hexahelicine, 4a-azoniaphenanthrophenanthrene perchlorate, has been synthesized by photo-cyclization of 2-styrylnaphthoquinolizinium perchlorate.
- Arai, Sadao,Yafune, Takuya,Okubo, Masaki,Hida, Mitsuhiko
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- Atom-efficient transition-metal-free arylation ofN,O-acetals using diarylzinc reagents through Zn/Zn cooperativity
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Exploiting the cooperative action of Lewis acid Zn(C6F5)2with diarylzinc reagents, the efficient arylation ofN,O-acetals to access diarylmethylamines is reported. Reactions take place under mild reaction conditions without the need for transtion-metal catalysis. Mechanistic investigations have revealed that Zn(C6F5)2not only acts as a Lewis acid activator, but also enables the regeneration of nucleophilic ZnAr2species, allowing a limiting 50 mol% to be employed.
- Borys, Andryj M.,Gil-Negrete, Jose M.,Hevia, Eva
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supporting information
p. 8905 - 8908
(2021/09/10)
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- Rediscovering aminal chemistry: Copper(ii) catalysed formation under mild conditions
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Aminals, the N,N analogues of acetals, have been thoroughly explored in organic chemistry, with a particular focus on heteroaromatic aldehyde lithiation. Nevertheless, the existing methodologies for their formation typically employ harsh conditions limiting their usefulness. In this work, we present an efficient and mild methodology for the preparation of aminals from aromatic aldehydes, including furanic platforms. These mild conditions allowed ease of access to a plethora of aminals and as such we set out to explore previously unaccessible potential applications. By studying the stability of various aminals, we were able to develop a simple aldehyde protecting group based on a commercial diamine which is deprotected under mind conditions. We developed a protocol for the scavenging of genotoxic aldehydes by taking advantage of our methodology and a diamine resin, as well as early studies on the development of a stimuli-responsive release system using a salycil aldehyde derived aminal. This journal is
- Afonso, Carlos A. M.,António, Jo?o P. M.,Gomes, Rafael F. A.,Mendon?a, Ricardo,Pereira, Juliana G.
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supporting information
p. 7484 - 7490
(2020/11/18)
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- Zinc-mediated allylation and alkylation of aminals in the presence of TMSCl and diisopropylamine
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(Chemical Equation Presented) An alkylation of aminals with organozinc reagents derived from allyl bromide, benzyl bromide, α-bromoacetate, and α-bromonitrile proceeded efficiently in the presence of TMSCl and diisopropylamine. This reaction system was applied to the synthesis of an antispasmodic: butaverine.
- Hatano, Bunpei,Nagahashi, Keita,Kijima, Tatsuro
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supporting information; body text
p. 9188 - 9191
(2009/04/11)
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- CHEMICAL PROCESSES AND COMPOUNDS DERIVED THEREFROM
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The present invention relates to N-substituted anilines and derivatives thereof and in particular to chemical processes for the preparation of N-substituted anilines and derivatives thereof.
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Page/Page column 30-31
(2010/10/19)
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- A new protocol for the preparation of aminals from aromatic aldehydes and their facile conversion to phosphonates
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A new and fast method for the preparation of aminals is reported from the reaction of aromatic aldehydes and secondary amines in the presence of potassium carbonate in high yields. The aminal can be converted to the corresponding iminum salt in reaction with acetyl chloride very easily and in very short time with high yield. Addition of trialkylphosphite, as one possible nucleophile, to the prepared iminium salt produces the α-amino phosphonate in very high yield.
- Dezfuli, Mohammad Karimi,Saidi, Mohammad Reza
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- A Scrutiny on the Reductive Amination of Carbonyl Compounds Catalyzed by Homogeneous Rh(I) Diphosphane Complexes
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The reductive amination of a series of aldehydes with secondary amines and H2 in the presence of a homogeneous Rh-diphosphane catalyst was studied in order to establish a general mechanism of this reaction and to identify conditions for the improvement of the amine/alcohol ratio in the product. Several possible intermediates as constituents of changing equilibria like half-aminals, N,O-acetals and aminals were observed in the reaction mixture by means of 1H NMR spectroscopy. In individual trials, these compounds could be successfully hydrogenated under the conditions applied for reductive amination (50 bar H2 pressure, MeOH). Some evidence is accumulated that half-aminals and N,O-acetals might be key intermediates of the reductive amination. Moreover, it was found that the formation of the undesired product alcohol is likely based on the reduction of the starting carbonyl compound. However, due to numerous equilibria consisting of several intermediates, general conclusions are hard to be drawn. Proof will be given that, in several cases, the efficiency of the reductive amination of aliphatic aldehydes can be significantly improved by prehydrogenation of the cationic [Rh(dppb)(COD)]+ complex.
- Tararov, Vitali I.,Kadyrov, Renat,Riermeier, Thomas H.,Boerner, Armin
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p. 200 - 208
(2007/10/03)
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- SYNTHESIS OF 6-METHYLISOQUINOLINOQUINOLIZINIUM SALT: EFFICIENT SYNTHESIS OF 2-(2-ARYLVINYL)QUINOLIZINIUM SALTS BY KNOEVENAGEL CONDENSATION USING ACETONITRILE AS A SOLVENT AND THE PHOTOCYCLIZATION
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In the Knoevenagel condensation of 2,3-dimethylquinolizinium salt with a vide variety of aromatic aldehydes in the presencce of piperidine, the use of acetonitrile as a solvent gave excellent yields (77-100percent) of 2-(2-arylvinyl)-quinolizinium salts.I
- Sato, Kiyoshi,Kano, Koji,Yafune, Takuya,Hida, Mitsuhiko,Arai, Sadao,Yamagishi, Takamichi
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p. 955 - 966
(2007/10/02)
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- Aminal Exchange
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Reactions of N-(α-benzotriazolylalkyl)-N,N-dialkylamines with the dialkylamine corresponding to the dialkylamino substituent afford symmetrical aminals in good yields.Treatment with other dialkylamines gives mixtures of the unsymmetrical and the two symme
- Katritzky, Alan R.,Yannakopoulou, Konstantina,Lang, Hengyuan
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p. 1867 - 1870
(2007/10/02)
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- N-(1-Haloalkyl)pyridinium Salts: Preparation and Use for New Syntheses of Other N-(1-Substituted-alkyl)pyridinium Salts, N,N'-(1-Alkylidene)bisamines, and N,N'-(1-Alkylidene)bisbenzazoles
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N-(1-Haloalkyl)pyridinium halides, obtained from an aldehyde, a thionyl halide, and pyridine, react readily with nucleophiles to yield N-(1-substituted -alkyl)pyridinium salts.N-(1-Bromoalkyl)pyridinium bromides rect readily with a wide range of nucleophiles to replace either the halogen ( by 1 mol ) or both halogen and pyridinium ( 2 mol ).They are useful precursors for the preparation of bisbenzazoles and other aminals under neutral and mild conditions.
- Anders, Ernst,Tropsch, Juergen G.,Katrizky, Alan R.,Rasala, Danuta,Eynde Vanden, Jean-Jacques
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p. 4808 - 4812
(2007/10/02)
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- Trimethylsilylamines III: mise en evidence du compose d'addition sur les aldehydes; preparation d'aminals et de β-dialkylamino β-arylesters en milieu aprotique
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Dialkylaminotrimethylsilanes react with aromatic aldehydes using trimethylsilyltriflate and tetrabutylammonium fluoride as catalysts and lead quantitatively to the corresponding aminals in aprotic media.The intermediate silylated hemiaminal can be characterized in many cases, mainly with pyridinecarbaldehydes.Aminals are obtained from aliphatic aldehydes using fluoride ion as catalyst.A one-pot synthesis of some β-dialkylamino β-arylesters from these reagents is described.
- Aube, Philippe,Christot, Isabelle,Combret, Jean-Claude,Klein, Jean-Louis
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p. 1009 - 1014
(2007/10/02)
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- Stereochemistry in the Knoevenagel Reaction of Methyl Arylsulphinylacetate and Aldehydes
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The stereochemistry of the mechanism of the amine-catalyzed Knoevenagel reaction has been studied.Simple treatment of methyl arylsulphinylacetate (1) and aldehydes (2) with a catalytic amount of a secondary amine produced thermodynamically stable E-alkene
- Tanikaga, Rikuhei,Konya, Naoto,Tamura, Tadashi,Kaji, Aritsune
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p. 825 - 830
(2007/10/02)
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- STEREOCHEMISTRY OF AMINE-CATALYZED KNOEVENAGEL REACTIONS
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The amine-catalyzed Knoevenagel reactions of aldehydes and active methylene compounds containing two activating groups were found to involve many reversible steps, and the diastereomeric intermediary condensation compounds yielded thermodynamically stable products via carbanionic intermediates stablized and sterically affected by two activating groups.
- Tanikaga, Rikuhei,Konya, Naoto,Kaji, Aritsune
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p. 1583 - 1586
(2007/10/02)
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- ACCESS TO AMINOPHENYLCARBENES VIA DIAZIRINE EXCHANGE REACTIONS
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Phenylbromodiazirine (1) reacts with a variety of primary and secondary amines affording a series of aminophenylcarbenes.
- Moss, Robert A.,Cox, D. Phillip,Tomioka, Hideo
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p. 1023 - 1026
(2007/10/02)
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