- Iron-Catalyzed Hydrogen Transfer Reduction of Nitroarenes with Alcohols: Synthesis of Imines and Aza Heterocycles
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A straightforward and selective reduction of nitroarenes with various alcohols was efficiently developed using an iron catalyst via a hydrogen transfer methodology. This protocol led specifically to imines in 30-91% yields, with a good functional group tolerance. Noticeably, starting from o-nitroaniline derivatives, in the presence of alcohols, benzimidazoles can be obtained in 64-72% yields when the reaction was performed with an additional oxidant, DDQ, and quinoxalines were prepared from 1,2-diols in 28-96% yields. This methodology, unprecedented at iron for imines, also provides a sustainable alternative for the preparation of quinoxalines and benzimidazoles.
- Wu, Jiajun,Darcel, Christophe
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p. 1023 - 1036
(2021/01/09)
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- Non-Bonding Electron Pair versus π-Electrons in Solution Phase Halogen Bond Catalysis: Povarov Reaction of 2-Vinylindoles and Imines
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The non-bonding electron pair (n-pair) of heteroatoms and π-electrons are both efficient halogen bond (XB) acceptors. In solid and gas phase studies, n-pairs generally prevail over π-bonding orbitals as XB acceptors, whereas few studies have been conducte
- Suzuki, Takumi,Kuwano, Satoru,Arai, Takayoshi
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supporting information
p. 3208 - 3212
(2020/07/04)
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- Iron-Catalyzed Nitrene Transfer Reaction of 4-Hydroxystilbenes with Aryl Azides: Synthesis of Imines via C=C Bond Cleavage
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C=C bond breaking to access the C=N bond remains an underdeveloped area. A new protocol for C=C bond cleavage of alkenes under nonoxidative conditions to produce imines via an iron-catalyzed nitrene transfer reaction of 4-hydroxystilbenes with aryl azides is reported. The success of various sequential one-pot reactions reveals that the good compatibility of this method makes it very attractive for synthetic applications. On the basis of experimental observations, a plausible reaction mechanism is also proposed.
- Peng, Yi,Fan, Yan-Hui,Li, Si-Yuan,Li, Bin,Xue, Jing,Deng, Qing-Hai
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p. 8389 - 8394
(2019/10/16)
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- Unsymmetrical indazolyl-pyridinyl-triazole ligand-promoted highly active iridium complexes supported on hydrotalcite and its catalytic application in water
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Herein, an indazolyl-pyridinyl-triazole ligand was synthesized and its iridium complex supported on hydrotalcite was characterized via X-ray power diffraction (XRD), X-ray photoelectron spectroscopy (XPS), energy dispersive X-ray (EDX) spectroscopy and transmission electron microscopy (TEM). This new heterogeneous catalyst bearing the unsymmetrical indazolyl-pyridinyl-triazole ligand exhibits high catalytic activity in water. Both functionalized amines and imines were obtained from the challenging selective reaction of benzylamines with arylamines through transfer hydrogenation and dehydrogenation under clean conditions. In particular, it was observed that this catalyst system showed good recovery performance in water. Mechanistic studies showed that this transformation occurs via amine dehydrogenation, hydrolysis and condensation processes. The direct capture of the reaction intermediate provides sufficient proof for this process.
- Ge, Chenyang,Sang, Xinxin,Yao, Wei,Zhang, Liang,Wang, Dawei
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supporting information
p. 1805 - 1812
(2018/04/30)
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- Homologation of α-aryl amino acids through quinone-catalyzed decarboxylation/Mukaiyama-Mannich addition
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A new method for amino acid homologation by way of formal C-C bond functionalization is reported. This method utilizes a 2-step/1-pot protocol to convert α-amino acids to their corresponding N-protected β-amino esters through quinone-catalyzed oxidative decarboxylation/in situ Mukaiyama-Mannich addition. The scope and limitations of this chemistry are presented. This methodology provides an alternative to the classical Arndt-Eistert homologation for accessing β-amino acid derivatives. The resulting N-protected amine products can be easily deprotected to afford the corresponding free amines.
- Haugeberg, Benjamin J.,Phan, Johnny H.,Liu, Xinyun,O'Connor, Thomas J.,Clift, Michael D.
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supporting information
p. 3062 - 3065
(2017/03/17)
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- Paclitaxel Biosynthesis: Adenylation and Thiolation Domains of an NRPS TycA PheAT Module Produce Various Arylisoserine CoA Thioesters
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Structure-activity relationship studies show that the phenylisoserinyl moiety of paclitaxel (Taxol) is largely necessary for the effective anticancer activity. Several paclitaxel analogues with a variant isoserinyl side chain have improved pharmaceutical
- Muchiri, Ruth,Walker, Kevin D.
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p. 1415 - 1425
(2017/03/23)
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- Enantioselective synthesis of 1,2,5,6-tetrahydropyridines (THPs): Via proline-catalyzed direct Mannich-cyclization/domino oxidation-reduction sequence: Application for medicinally important N-heterocycles
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An enantioselective multi-component synthesis of 1,2,5,6-tetrahydropyridines (THPs) has been developed through a one-pot domino-process. This transformation proceeds through proline-catalyzed direct Mannich reaction-cyclization of glutaraldehyde with in s
- Ramaraju, Panduga,Mir, Nisar A.,Singh, Deepika,Kumar, Indresh
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p. 60422 - 60432
(2016/07/11)
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- Ir-Catalyzed C?H Amidation of Aldehydes with Stoichiometric/Catalytic Directing Group
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Ir-catalyzed sp2C?H amidation of aldehydes with various anilines as stoichiometric or catalytic directing groups was accomplished. A wide range of substrates were selectively amidated in good to excellent yields with broad functional group tolerance. The iridacycle complexes were isolated, characterized, and proved as key intermediates. Kinetic studies and Hammett plots provided detailed understandings of this amidation. According to the mechanism, the electron-rich ArSO2N3was proved effective for intermolecular sp3C?H amidation.
- Zhang, Yun-Fei,Wu, Bin,Shi, Zhang-Jie
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supporting information
p. 17808 - 17812
(2016/11/28)
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- Studies on the interaction of isocyanides with imines: Reaction scope and mechanistic variations
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The interaction of imines with isocyanides has been studied. The main product results from a sequential process involving the attack of two units of isocyanide, under Lewis acid catalysis, upon the carbon-nitrogen double bond of the imine to form the 4-me
- Ghashghaei, Ouldouz,Manna, Consiglia Annamaria,Vicente-Garcia, Esther,Reves, Marc,Lavilla, Rodolfo
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supporting information
p. 12 - 17
(2014/01/23)
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- Synthesis of 4-imino-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxide through cycloaddition reaction of N-sulphinylanilines and N-(α-cyano-α-aryl) -methylanilines
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Through the normal mode of cycloaddition reaction of N-(α-cyano- α-aryl)-methylanilines (II) onto N-sulphinylanilines (III) has provided 2,3,5-triaryl-4-imino-2H,3H,5H-[1,2,5]thiadiazolidin-1-oxides (IV). The present protocol has advantage of convenient operation to synthesize heterocyclics in good yield.
- Kaur, Manpreet,Singh, Baldev
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p. 1157 - 1161
(2014/08/05)
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- Solvent-free synthesis, spectral correlations and antimicrobial activities of some aryl imines
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A series of aryl imines have been synthesized by Fly-ash: H 2SO4 catalyzed microwave assisted process under solvent-free conditions. The yields of the imines have been found to be more than 87%. The purity of all imines has been checked using their physical constants and spectral data as published earlier in literature. The UV λmaxCN(nm), infrared νCN(cm-1), NMR δ(ppm) of CH and CN spectral data have been correlated with Hammett substituent constants and F and R parameters using single and multi-linear regression analysis. From the results of statistical analysis, the effect of substituents on the above spectral data has been studied. The antimicrobial activities of All synthesised imines have been studied using Bauer-Kirby method.
- Suresh,Kamalakkannan,Ranganathan,Arulkumaran,Sundararajan,Sakthinathan,Vijayakumar,Sathiyamoorthi,Mala,Vanangamudi,Thirumurthy,Mayavel,Thirunarayanan
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p. 239 - 248
(2013/02/22)
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- Tetrahydroquinolines and benzazepines through catalytic diastereoselective formal [4 + 2]-cycloaddition reactions between donor-acceptor cyclopropenes and imines
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Regio- and diastereoselective Lewis acid catalyzed cycloaddition reactions between imines and donor-acceptor cyclopropenes generated from silyl-protected enoldiazoacetates provide direct access to stable cyclopropane-fused tetrahydroquinolines and, with cyclopropane ring opening under mild conditions, to 1H-benzazipine derivatives.
- Truong, Phong M.,Mandler, Michael D.,Zavalij, Peter Y.,Doyle, Michael P.
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supporting information
p. 3278 - 3281
(2013/07/26)
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- Catalytic asymmetric synthesis of dihydroquinazolinones from imines and 2-aminobenzamides
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An unprecedented catalytic asymmetric synthesis of aminal-containing heterocyclic compounds has been developed from imines and tethered nitrogen/nitrogen nucleophiles. In the presence of 10mol% of a commercially available chiral phosphoric acid, a range of aromatic, α,β- unsaturated, and aliphatic imines react with 2-aminobenzamides to give dihydroquinazolinones in good to excellent yields and ee. The enantioselectivity is significantly affected by the imine N-substituent through non-bonding interactions with the chiral phosphoric acid and the 2-aminobenzamide. Copyright
- Cheng, Dao-Juan,Tian, Yu,Tian, Shi-Kai
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supporting information; experimental part
p. 995 - 999
(2012/06/01)
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- Enantioselective one-pot three-component synthesis of propargylamines catalyzed by copper(I)-pyridine bis-(oxazoline) complexes
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A one-pot three-component coupling of aldehydes and amines in presence of terminal alkynes has been efficiently catalyzed by copper (I) complex of i-Pr-pybox-diPh 2b or s-Bu-pybox-diPh 2c. The process is simple and allows the synthesis of various propargy
- Bisai, Alakesh,Singh, Vinod K.
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supporting information; experimental part
p. 3480 - 3486
(2012/06/04)
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- GREEN SYNTHESIS OF ARYL ALDIMINES USING ETHYL LACTATE
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The present invention relates to a method for preparing aryl aldimines. In particular, the present invention relates to methods of preparing aryl aldimines that uses environmentally friendly solvent systems.
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Page/Page column 5-6
(2011/08/22)
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- One-pot synthesis and fluorescence properties of 2-arylquinolines
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The one-pot synthesis of 2-arylquinoline with arylamines, arylaldehyde, and 1,1-diethoxyethane were studied using a catalytic amount ytterbium triflate. Various 2-arylquinolines showed fluorescence properties and the fluorescence was quenched by introduci
- Sueki, Shunsuke,Okamoto, Chiharu,Shimizu, Isao,Seto, Keisuke,Furukawa, Yukio
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supporting information; experimental part
p. 385 - 390
(2010/07/09)
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- Synthesis of densely substituted trans-configured 4-acylated piperidine-2,4-diones as 3:1 Adducts of imines and ketenes
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An operationally simple method is described to form densely substituted diastereomerically pure trans-configured and potentially biologically interesting 5,6-dihydropyridone derivatives as 3:1 adducts of ketenes formed in situ from acyl bromides and aromatic imines.
- Cabrera, Jose,Hellmuth, Tina,Peters, Rene
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experimental part
p. 4326 - 4329
(2010/09/03)
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- Catalyzed addition of diazoacetoacetates to imines: Synthesis of highly functionalized aziridines
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The addition of diazoacetoacetates to aromatic imines derived from p-methoxyaniline is achieved using dirhodium tetraacetate as the catalyst. Highly functionalized aziridines are obtained in good yield and with excellent stereoselectivity. 2-Diazo-1,3-diketones also provide good yields of aziridines, but dimethyl diazomalonate is inactive in the transformation. The diazoacetoacetates of chiral alcohols are also examined in the reaction and moderate diastereoselectivity is achieved with (R)-pantolactone-derived diazoacetoacetate. A reaction mechanism through metal-carbene and azomethine ylide is proposed.
- Zhang, Xue-Jing,Yan, Ming,Huang, Dan
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experimental part
p. 187 - 192
(2009/04/07)
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- Proline-mediated enantioselective construction of tetrahydropyridines via a cascade Mannich-type/intramolecular cyclization reaction
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A highly diastereo- and enantioselective synthesis of 2,3-disubstituted tetrahydropyridines was accomplished via a proline-mediated cascade Mannich-type/intramolecular cyclization reaction from preformed N-PMP (p-methoxyphenyl) aldimines and inexpensive aqueous tetrahydro-2H-pyran-2,6- diol.
- Han, Rong-Gang,Wang, Yao,Li, Yu-Ye,Xu, Peng-Fei
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supporting information; experimental part
p. 1474 - 1478
(2009/07/18)
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- β-Lactam derivatives as enzyme inhibitors: Halogenated β-lactams and related compounds
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Different modifications of the imine - acyl chloride reaction were used for the synthesis of 3-mono- and 3,3-dihalogenated 1,4-diaryl substituted β-lactams. Furthermore, these β-lactams were modified by halogen substitution either at the aryl at position
- Elriati, Ali,Loose, Jutta,Mayrhofer, Roswitha,Bergmann, Hans-Joachim,Otto, Hans-Hartwig
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experimental part
p. 835 - 846
(2009/09/06)
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- Enantioselective direct aza hetero-Diels-Alder reaction catalyzed by chiral Bronsted acids
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(Chemical Equation Presented) The first chiral Bronsted acid-catalyzed asymmetric direct aza hetero-Diels-Alder reaction has been described. The phosphoric acids, prepared from binol and H8-binol derivatives, have shown catalytic ability for th
- Liu, Hua,Cun, Lin-Feng,Mi, Ai-Qiao,Jiang, Yao-Zhong,Gong, Liu-Zhu
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p. 6023 - 6026
(2007/10/03)
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- Nickel-catalyzed multi-component connection reaction of isoprene, aldimines (lactamines), and diphenylzinc
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Ni(acac)2 catalyzes the four-component connection reaction of diphenylzinc, isoprene, aromatic aldehydes, and aromatic amines in this order and provides stereochemically homogeneous (E)-1-arylamino-1-aryl-3-methyl-5-phenyl-3-pentenes (1) in excellent yields. Aliphatic aldehydes react similarly and give (E)-1-arylamino-1-alkyl-3-methyl-5-phenyl-3-pentenes (1) in slightly reduced yields. When the alkyl groups are bulky, in addition to 1 are formed (E)-1-arylamino-1-alkyl-4-methyl-5-phenyl-3-pentenes (1′) as the minor products. Lactamines prepared in situ from five- and six-membered lactols and aromatic amines are more reactive than alkyl aldehyde aldimines and furnish (E)-4-arylamino-6-methyl-8-phenyl-6-octen-1-ols (4) and (E)-5-arylamino-7-methyl-9- phenyl-7-nonen-1-ols (5), respectively, in good yields with excellent E-stereoselectivity.
- Kojima, Keisuke,Kimura, Masanari,Ueda, Satoshi,Tamaru, Yoshinao
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p. 7512 - 7520
(2007/10/03)
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- Nickel-catalyzed four-component connection of oraganoaluminium (organozinc), isoprene, aldehydes and amines: Stereo- and regioselective synthesis of trisubstituted (E)-homoallylamines
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Ni(acac)2 catalyzes the four-component connection reaction of trimethylaluminium (or diphenylzinc), isoprene, aromatic aldehydes and p-anisidine in this order and provides (E)-1-aryl-1-(p-methoxyphenyl)amino-3- methyl-3-hexenes (or (E)-1-aryl-1
- Kojima, Keisuke,Kimura, Masanari,Tamaru, Yoshinao
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p. 4717 - 4719
(2007/10/03)
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