- Formation of Amides from Imines via Cyanide-Mediated Metal-Free Aerobic Oxidation
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A new protocol for the direct formation of amides from imines derived from aromatic aldehydes via metal-free aerobic oxidation in the presence of cyanide is described. This protocol was applicable to various aldimines, and the desired amides were obtained in moderate to good yields. Mechanistic studies suggested that this aerobic oxidative amidation might proceed via the addition of cyanide to imines followed by proton transfer from carbon to nitrogen in the original imines, leading to carbanions of α-amino nitriles, which undergo subsequent oxidation with molecular oxygen in air to provide the desired amide compounds.
- Seo, Hong-Ahn,Cho, Yeon-Ho,Lee, Ye-Sol,Cheon, Cheol-Hong
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p. 11993 - 11998
(2016/01/09)
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- Reduction of 1,2-dicarbonyl compounds and of their N-phenylimine derivatives by sodium cyanide under aprotic conditions
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Some aromatic 1,2-dicarbonyl compounds, i.e. 9,10-phenanthrenequinone, acenaphthenequinone and benzil, and their corresponding N-phenyl monoimines, have been reduced, using dry acetonitrile as the solvent, in the presence of sodium cyanide as a reducing agent. Comparative potentiostatic preparative-scale electrolysis is described.
- Batanero, Belen,Hamrouni, Kaouthar,Barba, Fructuoso,Barba, Isidoro,Boujlel, Khaled,Benkhoud, Mohamed Lamine
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p. 1284 - 1288
(2015/12/12)
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- Synthesis of iminonitriles by oxone/tbab-mediated one-pot oxidative three-component strecker reaction
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Oxidative three-component reaction of aldehydes, amines, and TMSCN in a biphasic solvent system (toluene/H2O) containing Oxone, tetra-n-butylammonium bromide (TBAB) and sodium bicarbonate afforded α-iminonitriles in good to excellent yields. This oxidative Strecker reaction was applicable to a wide range of aldehydes and amines, aromatic or aliphatic, of different electronic and steric properties. Substituted 1-aza-2-cyano-1,3-dienes were also accessible using α,β-unsaturated aldehydes as inputs.
- Gualtierotti, Jean-Baptiste,Schumacher, Xavier,Wang, Qian,Zhu, Jieping
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supporting information
p. 1380 - 1386
(2013/07/05)
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- Construction of highly functional α-amino nitriles via a novel multicomponent tandem organocatalytic reaction: A facile access to α-methylene γ-lactams
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The first tertiary amine-catalyzed multicomponent tandem Strecker-allylic-alkylation (SAA) reaction has been developed, which provides a facile access to functionalized α-amino nitriles, which could be readily converted into α-methylene-γ-butyrolactams. The Royal Society of Chemistry 2012.
- Pan, Feng,Chen, Jian-Ming,Zhuang, Zhe,Fang, Yin-Zhi,Zhang, Sean Xiao-An,Liao, Wei-Wei
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p. 2214 - 2217
(2012/04/10)
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- Elusive ethynyl azides: Trapping by 1,3-dipolar cycloaddition and decomposition to cyanocarbenes
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Although they decompose rapidly to produce cyanocarbenes, ethynyl azides were generated from (chloroethynyl)arenes and trapped for the first time by 1,3-dipolar cycloaddition at cyclooctyne.
- Banert, Klaus,Hagedorn, Manfred,Wutke, Jens,Ecorchard, Petra,Schaarschmidt, Dieter,Lang, Heinrich
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supporting information; experimental part
p. 4058 - 4060
(2010/09/06)
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- Synthesis of highly functionalized 2(1H)-pyrazinone 3-carboxamide scaffolds
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(Chemical Equation Presented) Synthesis of highly functionalized 2(1H)-pyrazinone 3-carboxamide derivatives is reported. A one-pot, two-step process including the base-mediated reaction of N,N-disubstituted aminoacetonitrile derivatives 18 with 3,5-dihalo
- Pawar, Sonalika V.,Pawar, Vijaykumar G.,Dehaen, Wim,De Borggraeve, Wim M.
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scheme or table
p. 4473 - 4476
(2009/05/07)
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- One-pot three-component sysnthesis of α-iminonitriles by IBX/TBAB-mediated oxidative strecker reaction
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The reaction of aldehydes, amines, and TMSCN in the presence of 2-iodoxybenzoic acid (IBX) and tetrabutylammonium bromide (TBAB) afforded α-iminonitriles in good to excellent yields under mild conditions. The presence of TBAB is essential for this transformation. The methodology was applied to a two-step synthesis of indolizidine via a microwave-assisted intramolecular cycloaddition of α-iminonitrile.
- Fontaine, Patrice,Chiaroni, Angle,Masson, Geraldine,Zhu, Jieping
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supporting information; experimental part
p. 1509 - 1512
(2009/04/10)
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- Lithium bromide catalyzed Ehrlich-Sachs reactions using solvent-free conditions
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Lithium bromide proves to be an efficient catalyst for Ehrlich-Sachs reaction of nitroso arenes with active methylene compounds under microwave irradiation through simple solvent-free reaction conditions.
- Laskar,Prajapati,Sandhu
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p. 1427 - 1432
(2007/10/03)
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- Oxidation of amines with hyper valent Tert-butylperoxyiodanes: Synthesis of imines and Tert-butylperoxyamino acetalsh
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Reaction of secondary amines with 1-tert-butylperoxy-1,2-benziodoxol-3(1H)-one (2) undergoes dehydrogenation to afford imines in the presence of K2CO3, while oxidation of tertiary amines without base produces tert-butylperoxyamino acetals.
- Ochiai, Masahito,Kajishima, Daisuke,Sueda, Takuya
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- Synthesis of Nitrogen Heterocycles by Condensation of the Conjugate Base of Open-Chain Reissert Compound Analogs with Vinyltriphenylphosphonium Bromide (Schweizer's Salt)
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Reaction of the conjugate base of several open-chain Reissert compound analogs with vinyltriphenylphosphonium bromide is shown to afford a convenient route to substituted pyrroles.The condensation is a two-step process involving an initial reversible addition to form an unstabilized Wittig reagent followed by an intramolecular Wittig reaction upon the carbonyl group of the tertiary amide functionality with concomitant elimination of HCN.Several applications to the synthesis of 1,2,5-trisubstituted pyrroles are presented, together with attempts to expand this methodology to the synthesis of other heterocyclic systems.
- Cooney, John V.,Beaver, Bruce D.,McEwen, William E.
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p. 635 - 642
(2007/10/02)
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- A NEW FACILE METHOD FOR THE PREPARATION OF α-IMINONITRILES FROM ALDONITRONES AND CYANOTRIMETHYLSILANE.
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α-Iminonitriles have been obtained in good yields by reacting aldonitrones and cyanotrimethylsilane.
- Dutta, D. K.,Prajapati, D.,Sandhu, J. S.,Baruah, J. N.
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p. 335 - 340
(2007/10/02)
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- Ruthenium-catalysed Oxidation of Secondary Amines to Imines using t-Butyl Hydroperoxide
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The ruthenium-catalysed oxidation of secondary amines with t-butyl hydroperoxide under mild conditions affords the corresponding imines in high yields.
- Murahashi, Shun-Ichi,Naota, Takeshi,Taki, Hiroshi
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p. 613 - 614
(2007/10/02)
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- OXIDATIVE BENZOIN REACTIONS
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A one-pot synthesis (yields over 50percent) of methyl and ethyl esters from aldehydes (and the corresponding alcohol), using aromatic nitrocompounds as oxidizing agents under the catalytic action of cyanide ion or of a conjugate base of a thiazolium ion, is described.A variety of by-products (α-hydroxybenzylidenaniline (16), α-methoxybenzylidenaniline (21), α-cyanobenzylidenaniline (27), N1-hydroxy-N1,N2-diphenylbenzamidine (28), and others) have been identified.
- Castells, J.,Pujol, F.,Llitjos, H.,Moreno-Manas, M.
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p. 337 - 346
(2007/10/02)
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- Une nouvelle methode de transformation des aldehydes aromatiques en α-iminonitriles Ar-C(CN)=N-R
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The reaction with amines of bromoderivates Ar-CBr(SEt)-CN, easily obtained in high yields from aldehydes, provides a convinient route to C-aryl N-alkyl (or aryl) α-iminonitriles.
- Pochat, Francis
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p. 955 - 956
(2007/10/02)
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