- Surfactant dependent pH controlled "off-on", "off-on-off" and "on-off" fluorescent switches exhibited by N-benzylidenenaphthalen-1-amine
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N-benzylidenenaphthalen-1-amine (L) acts as pH dependent "off-on", "off-on-off" and "on-off" fluorescent switch in 1:1 (v/v) CH3CN:H2O depending on the presence of anionic sodiumdocdecyl sulphate (SDS), neutral triton X-100 (TX-100)
- Kumar, Jutika,Sarma, Manas Jyoti,Phukan, Prodeep,Das, Diganta Kumar
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Read Online
- Stereoselective synthesis of new β-lactams from the main functional group of indomethacin
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New β-lactams were synthesized in moderate yields from indomethacin, which is currently used as a drug to relieve pain such as arthritis, muscle and bone damage. The reaction was carried out by [2 + 2] cycloaddition of the in situ formed indomethacinyl ke
- Amiri, Mojgan,Islami, Mohammad Reza,Mortazavi, Zahra Fahimeh al-Sadat
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- Copper-Catalyzed Intramolecular Amination of C(sp3)-H Bond of Secondary Amines to Access Azacycles
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The cross-coupling of C-N bond directly from inert C-H bonds is an ideal approach to synthesize saturated azacycles due to its high efficiency and atom economy. In this article, a copper-catalyzed intramolecular amination via the cross coupling of C(sp3)-H and N-H bonds of secondary amine has been reported, which exhibit excellent chemo- and regioselectivity, extensive substrate scope, and functional group tolerance in good to excellent yield, offering an efficient pathway to build nitrogen-containing heterocycle skeletons.
- Jin, Ruo-Xing,Dai, Jing-Cheng,Li, Yan,Wang, Xi-Sheng
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supporting information
p. 421 - 426
(2021/01/26)
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- Highly efficient and selective one-pot tandem imine synthesis via amine-alcohol cross-coupling reaction catalysed by chromium-based MIL-101 supported Au nanoparticles
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One-pot tandem synthesis of imines from alcohols and amines is regarded as an effective, economic and green approach under mild conditions. In this work, Au nanoparticles (NPs) dispersed on MIL-101 (Au/MIL-101) were demonstrated as highly active and selective bifunctional heterogeneous catalyst for production of various imine derivatives with excellent yields, via amine-alcohol cross-coupling reaction at 343 K in an open flask under an Ar atmosphere. Various physicochemical techniques, including inductively coupled plasma optical emission spectroscopy (ICP-OES), powder X-ray diffraction (P-XRD), X-ray photoelectron spectroscopy (XPS) transmission electron microscopy (TEM) and N2 adsorption-desorption, were used to characterize of the Au/MIL-101 catalyst. The obtained bifunctional catalyst is highly active and selective towards one-pot imine formation and exhibited the highest TOF (30.15-51.47 h?1) among all the ever-reported MOF-supported Au catalysts. The reaction mechanism of the imine formation from alcohol and amine over Au/MIL-101 catalyst was proposed. Mechanism experiment results demonstrate that Au NPs highly effective in activating oxidation of benzyl alcohol to benzaldehyde while the Lewis acid sites on MIL-101 catalyzed the second condensation step without interfering with the oxidation step. As a result, the excellent catalytic performance of Au/MIL-101 can be ascribed to the synergistic effect between Au NPs with Lewis acid sites in MIL-101.
- Gülcan, Mehmet,Gumus, Ilkay,Karatas, Yasar,Ruzgar, Adem
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- Catalyst- And Solvent-Free Synthesis of α-Amino Polyfluoroalkylphosphonates from Bis(fluoroalkyl) Phosphonates and Aldimines
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The catalyst- and solvent-free reaction between bis(fluoroalkyl) phosphonates and aldimines occurs under mild conditions (20-22 °C, 0.25-4 h) to afford a new family of α-amino polyfluoroalkylphosphonates in up to quantitative yields.
- Arbuzova, Svetlana N.,Gusarova, Nina K.,Kazantseva, Tatyana I.,Kolyvanov, Nikita A.,Trofimov, Boris A.,Verkhoturova, Svetlana I.,Zinchenko, Sergey V.
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p. 1531 - 1540
(2020/05/19)
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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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- Catalyst- And solvent-free efficient access to: N -alkylated amines via reductive amination using HBpin
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A sustainable approach which works under catalyst- and solvent-free conditions for the synthesis of structurally diverse secondary amines has been uncovered. This one-pot protocol works efficiently at room temperature and is compatible with a wide range of sterically and electronically diverse aldehydes and primary amines. Notably, this simple process offers scalability, excellent functional group tolerance, chemoselectivity, and is also effective at the synthesis of biologically relevant molecules. This journal is
- Bauri, Somnath,Pandey, Vipin K.,Rit, Arnab
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supporting information
p. 3853 - 3857
(2020/07/27)
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- Silver nanoparticles stabilized by a metal-organic framework (MIL-101(Cr)) as an efficient catalyst for imine production from the dehydrogenative coupling of alcohols and amines
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In this paper, we present silver nanoparticles supported on a metal-organic framework (Ag@MIL-101) as a catalyst for the one-pot tandem synthesis of imines from alcohols and amines. The Ag@MIL-101 catalyst was fabricated using the liquid phase impregnation technique as an easy and effective method. The morphology and chemical structure of the prepared catalyst were systemically evaluated by inductively coupled plasma optical emission spectroscopy (ICP-OES), powder X-ray diffraction (P-XRD), X-ray photoelectron spectroscopy (XPS) and transmission electron microscopy (TEM). The highly crystalline feature of the Ag metal nanoparticles on bifunctional MIL-101(Cr) was revealed by TEM and HRTEM analyses. The Ag@MIL-101 catalyst was examined as a catalyst for the synthesis of different imine derivatives. The catalytic performance of the Ag@MIL-101 catalyst was monitored by GC-MS and 1H-NMR analyses for the dehydrogenative coupling of alcohols and amines. Furthermore, the effect of various factors such as the amount of catalyst, base, temperature and solvent was investigated to optimize the conditions for the best performance of the Ag@MIL-101 catalyst. Catalytic activity test results showed that the Ag@MIL-101 catalyst has a good catalytic activity with TOF values in the range of 12.7-14.6 h-1 in the synthesis of various imines.
- Gumus, Ilkay,Karata?, Yas?r,Gülcan, Mehmet
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p. 4990 - 4999
(2020/11/02)
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- Synthesis of Imines via Reactions of Benzyl Alcohol with Amines Using Half-Sandwich (η6-p-cymene) Ruthenium(II) Complexes Stabilised by 2-aminofluorene Derivatives
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A new class of half-sandwich (η6-p-cymene) ruthenium(II) complexes supported by 2-aminofluorene derivatives [Ru(η6-p-cymene)(Cl)(L)] (L?=?2-(((9H-fluoren-2-yl)imino)methyl)phenol (L1), 2-(((9H-fluoren-2-yl)imino)methyl)-3-methoxyphenol (L2), 1-(((9H-fluoren-2-yl)imino)methyl)naphthalene-2-ol (L3) and N-((1H-pyrrol-2-yl)methylene)-9H-fluorene-2-amine (L4)) were synthesized. All compounds were fully characterized by analytical and spectroscopic techniques (IR, UV–Vis, NMR) and also by mass spectrometry. The solid state molecular structures of the complexes [Ru(η6-p-cymene)(Cl)(L2)], [Ru(η6-p-cymene)(Cl)(L3)] and [Ru(η6-p-cymene)(Cl)(L4)] revealed that the 2-aminofluorene and p-cymene moieties coordinate to ruthenium(II) in a three-legged piano-stool geometry. The synthesized complexes were used as catalysts for the dehydrogenative coupling of benzyl alcohol with a range of amines (aliphatic, aromatic and heterocyclic). The reactions were carried out under thermal heating, ultrasound and microwave assistance, using solvent or solvent free conditions, and the catalytic performance was optimized regarding the solvent, the type of base, the catalyst loading and the temperature. Moderately high to very high isolated yields were obtained using [Ru(η6-p-cymene)(Cl)(L4)] at 1?mol%. In general, microwave irradiation produced better yields than the other two techniques irrespective of the nature of the substituents.
- Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Durgadevi, Anandhan,Abinaya, Ravikumar,Alves, Luis G.,Martins, Ana Margarida,Bharathi, Kuppannan Shanmuga
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- Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
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Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.
- Ji, Fanghua,Li, Jianxiao,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
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p. 104 - 112
(2018/02/19)
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- Direct synthesis of imines by 9-azabicyclo-[3,3,1]nonan-N-oxyl/KOH-catalyzed aerobic oxidative coupling of alcohols and amines
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A simple and efficient method for preparation of imines by the oxidative coupling of benzyl alcohols with aromatic amines or aliphatic amines was developed. The reaction was catalyzed by 9-azabicyclo[3.3.1]nonan-N-oxyl (ABNO)/KOH with air as the economic and green oxidant. Under the optimal reaction conditions, a variety of imines were obtained in 80%-96% isolated yields.
- Wan, Yan,Ma, Jia-Qi,Hong, Chao,Li, Mei-Chao,Jin, Li-Qun,Hu, Xin-Quan,Hu, Bao-Xiang,Mo, Wei-Min,Sun, Nan,Shen, Zhen-Lu
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p. 1269 - 1272
(2017/10/26)
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- Umpolung Addition of Aldehydes to Aryl Imines
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One of the classical ways to synthesize amines involves the coupling of carbonyl compounds and imines, either through enolate chemistry or acyl-based carbanion equivalents. We herein report an alternative strategy that is based on the use of aldehydes as alkyl carbanion equivalents in a reductive coupling with aryl imines. A wide array of secondary amines can be synthesized in moderate to high yields. This reaction is mediated by hydrazine and catalyzed by ruthenium(II) complexes, and it tolerates various functional groups, such as esters, amides, and nitriles.
- Chen, Ning,Dai, Xi-Jie,Wang, Haining,Li, Chao-Jun
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supporting information
p. 6260 - 6263
(2017/05/19)
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- Stereoselective Synthesis of 3-(5-Benzoyl-1-methyl-1 H -pyrrol-2-yl)-2-azetidinone Derivatives via an in Situ Generated Ketene
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A short route toward β-lactams from tolmetin has been developed. In the key step, a ketene was generated on the C-2 of pyrrole ring and reacted with aromatic imines to form trans -β-lactams as the only observed products. The identification of the ketene was confirmed by reaction with the stable free radical TEMPO (TO·).
- Bananezhad, Behjat,Islami, Mohammad Reza
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supporting information
p. 1453 - 1456
(2017/07/22)
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- Silica functionalized Cu(II) acetylacetonate Schiff base complex: An efficient catalyst for the oxidative condensation reaction of benzyl alcohol with amines
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Silica functionalized Cu(II) acetylacetonate Schiff base complex via the one pot reaction of silica functionalized 3-aminopropyltriethoxysilane with acetyl acetone and copper acetate has been reported. The synthesized material was well characterized by analytical techniques such as FT-IR, UV-DRS, XRD, SEM-EDX, HR-TEM, EPR, ICP-AES and BET analysis. The characterization results confirmed the grafting of Cu(II) Schiff base complex on the silica surface. The catalytic activity of synthesized silica functionalized Cu(II) acetylacetonate Schiff base complex was evaluated through the oxidative condensation reaction of benzyl alcohol to imine.
- Anbarasu,Malathy,Karthikeyan,Rajavel
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p. 305 - 312
(2017/06/27)
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- A Route to Polysubstituted Aziridines from Carbenes and Imines through a Nondiazo Approach
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An efficient method for the synthesis of polysubstituted aziridines utilizing enynones and imines is described. This transformation is achieved through the reaction of imines with donor/donor carbene intermediates, which were generated in situ from the cyclization of enynones. Furthermore, the resulted aziridines were good 1,3-dipoles, which could be efficiently trapped by dipolarophiles to give five-membered heterocycles. The obvious advantages of wide substrate scopes, mild reaction conditions, and high atom efficiency make this system highly appealing for construction of polysubstituted aziridines, 2,5-dihydropyroles, and 1,2,4-triazolidines.
- Luo, Hejiang,Chen, Kai,Jiang, Huanfeng,Zhu, Shifa
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supporting information
p. 5208 - 5211
(2016/11/02)
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- A Solvent-Free Process for Synthesis of Imines by Iron-Catalyzed Oxidative Self- or Cross-Condensation of Primary Amines Using Molecular Oxygen as Sole Oxidant
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Abstract: The synthesis of imines by oxidative self- or cross-condensation of primary amines has been achieved using iron(II) bromide as the catalyst. The protocol is ligand-free, additive-free, solvent-free, and high-yielding and utilizes renewable oxygen as sole oxidant. The reaction tolerated a wide range of functionalities. Graphical Abstract: [Figure not available: see fulltext.]
- Gopalaiah, Kovuru,Saini, Anupama
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p. 1648 - 1654
(2016/08/30)
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- Load manganese oxidizing catalytic chipboard spreading method for one-step synthesis of imines
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The invention belongs to the technical fields of chemistry and chemical engineering, and concretely relates to a method for one step synthesis of imine through catalyzing alcohol and amine by supported manganese oxide. A reaction of alcohol and amine is carried out in a solvent or solvent-free state at 60-90DEG C for 6-48h with the supported manganese oxide as a catalyst and molecular oxygen or air as an antioxidant to realize one step synthesis of a corresponding imine compound. The valence of manganese in the catalyst is +2, +3 or +4, the general formula of the catalyst is MnOx, and a carrier is hydroxyapatite (Ca10(PO4)6(OH)2). The catalyst still has very good activity and selectivity after the catalyst is reused at least 9 times. The catalyst used in the method has the characteristics of simple preparation, cheapness, high reaction selectivity and environmental protection.
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Paragraph 0062; 0063
(2017/02/02)
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- Highly Stereoselective Synthesis of Saccharin-Substituted β-Lactams via in Situ Generation of a Heterosubstituted Ketene and a Zwitterionic Intermediate as Potential Antibacterial Agents
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Highly stereoselective synthesis of saccharin derivatives containing functionalized 2-azetidinone moiety was achieved starting from saccharin as an available precursor. The approach to these valuable heterocyclic scaffolds involves a formal [2π + 2π] cycloaddition between Schiff bases and the saccharinylketene as a novel ketene which was generated in situ and an electrocyclic reaction of a zwitterionic intermediate. The identification of the ketene was confirmed by reaction with the stable free radical TEMPO (TO?). Also, the antimicrobial activities of some new substituted saccharin against nine standard bacteria, four bacteria which were isolated from clinical samples and one yeast, were evaluated.
- Mortazavi, Zahra F. A.,Islami, Mohammad R.,Khaleghi, Moj
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supporting information
p. 3034 - 3037
(2015/06/30)
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- Direct imine formation by oxidative coupling of alcohols and amines using supported manganese oxides under an air atmosphere
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Manganese oxides loaded on various supports have been prepared and studied for the direct imine formation by oxidative coupling of alcohols and amines. Among the catalysts, hydroxyapatite supported manganese oxides (MnO x/HAP) show the best activity and selectivity for this reaction in the absence of an additional base using air as the environmentally benign terminal oxidant. NH3-/CO2-TPD results show that the amphoteric properties of MnOx/HAP are crucial for this reaction to obtain a satisfactory yield. Various aromatic alcohols and amines are smoothly transformed into the corresponding imines in good to excellent yields. The catalyst is reusable and gives 98% yield of the product in all 9 reuse tests. Compared with the fresh catalyst, the XRD and SEM of the reactivated MnO x/HAP after nine reactions do not show any obvious change. This journal is the Partner Organisations 2014.
- Chen, Bo,Li, Jun,Dai, Wen,Wang, Lianyue,Gao, Shuang
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p. 3328 - 3334
(2014/06/10)
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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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- PEG400-enhanced synthesis of gem-dichloroaziridines and gem-dichlorocyclopropanes via in situ generated dichlorocarbene
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PEG400 is employed as an efficient phase transfer catalyst for the cycloaddition reaction of imines with dichlorocarbene, which is generated in situ from chloroform and sodium hydroxide, to give gem-dichloroaziridines in moderate to excellent yields at ambient temperature. This protocol is also extended to the synthesis of cyclopropanes from a variety of alkenes. In this study, PEG400 behaves as a phase transfer reagent thanks to its ability to coordinate with alkali metal cations. Notably, the one-pot synthesis of gem-dichloroaziridines from benzaldehyde and aromatic amines has also been successfully performed. The in situ generated acid, derived from CO2 and H2O, can also be effectively applied to promote the amide synthesis via the gem-dichloroaziridine pathway. The application of the gem-dichlorocyclopropane as a platform chemical is also briefly demonstrated, to afford the 2-phenylacrylaldehyde derivative via a ring-opening reaction. The Royal Society of Chemistry 2013.
- Song, Qing-Wen,Yu, Bing,Liu, An-Hua,He, Ying,Yang, Zhen-Zhen,Diao, Zhen-Feng,Song, Qing-Chuan,Li, Xue-Dong,He, Liang-Nian
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p. 19009 - 19014
(2013/10/22)
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- Formation of C=N bonds by the release of H2: A new strategy for synthesis of imines and benzazoles
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A new strategy for synthesis of imines using the approach of release of H2 has been developed. This oxidant- and acceptor-free Pd/C catalysis protocol is further applied to synthesis of benzoxazoles, benzimidazoles, and benzothiazoles through a one-pot cascade reaction with notably high yields. The Royal Society of Chemistry 2013.
- Jin, Xukang,Liu, Yuxiao,Lu, Qiongqiong,Yang, Dejun,Sun, Jiangkai,Qin, Shuangshuang,Zhang, Jingwu,Shen, Jiaxuan,Chu, Changhu,Liu, Renhua
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supporting information
p. 3776 - 3780
(2014/03/21)
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- Preparation of imines by oxidative coupling of benzyl alcohols with amines catalysed by dicopper complexes
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Complexation of 2,7-bis(2-pyridyl)-1,8-naphthyridine (bpnp) with Cu 2O in formic acid under aerobic conditions provided a dicopper complex [Cu2(bpnp)(μ-OH)(HCOO)3] (1). This complex has been characterized by X-ray crystallographic and spectroscopic analysis. With O2 as the oxidant, complex 1 is an efficient catalyst for the oxidative coupling of alcohols with amines or diamines, leading to the corresponding imines or diimines in good to excellent yields. A dicopper complex has been found to be an efficient catalyst for the oxidative coupling of benzyl alcohols with amines or diamines, leading to the corresponding imines or diimines in good to excellent yields without using any organic solvent. Copyright
- Lan, Yung-Syuan,Liao, Bei-Sih,Liu, Yi-Hong,Peng, Shie-Ming,Liu, Shiuh-Tzung
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supporting information
p. 5160 - 5164
(2013/11/06)
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- Iron-catalyzed direct synthesis of imines from amines or alcohols and amines via aerobic oxidative reactions under air
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Abundant and cheap iron readily catalyzed the aerobic oxidative reactions of primary amines, secondary amines, benzylamines with anilines, and alcohols with amines by directly using air as the economic and safe oxidant, providing several direct, practical, and greener approaches for the preparation of useful imines.
- Zhang, Erlei,Tian, Haiwen,Xu, Sendong,Yu, Xiaochun,Xu, Qing
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supporting information
p. 2704 - 2707
(2013/07/19)
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- Bifunctional ruthenium(II) PCP pincer complexes and their catalytic activity in acceptorless dehydrogenative reactions
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New air-stable ruthenium complex 1, bearing the dibenzobarrelene-based cooperating ligand, was synthesized in 96% yield and fully characterized. The examination of its coordination chemistry revealed that the ruthenium center in 1 is slightly distorted from octahedral geometry, and 31P NMR is consistent with the formation of trans-spanned pincer complexes bearing strongly bent dibenzobarrelene-based ligands. The catalytic activity of the new complex was examined in acceptorless dehydrogenation of alcohols and acceptorless dehydrogenative coupling of alcohols with amines.
- Musa, Sanaa,Fronton, Sveta,Vaccaro, Luigi,Gelman, Dmitri
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p. 3069 - 3073
(2013/07/05)
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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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- Oxidative imination of toluenes catalyzed by Pd-Au/silica gel under mild reaction conditions
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A Pd-Au/SiO2 catalyst was prepared for the oxidative imination of toluenes with up to 99% yields in the absence of dehydrating agents under mild conditions. Nanoparticles with a PdO layer and PdO-Au core may be the active structure for the reaction.
- Cui, Xinjiang,Shi, Feng,Deng, Youquan
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supporting information; experimental part
p. 7586 - 7588
(2012/10/07)
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- Au/Ag-Mo nano-rods catalyzed reductive coupling of nitrobenzenes and alcohols using glycerol as the hydrogen source
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A highly efficient Au/Ag-Mo nano-rods catalyst was prepared for the one-pot synthesis of imine and amine using equal molar ratio of nitrobenzene and alcohol as starting materials, and bio-based glycerol as the hydrogen source. The reaction mechanism of the nitrobenzene reduction, amine and aldehyde coupling, and imine reduction was explored.
- Cui, Xinjiang,Zhang, Chengming,Shi, Feng,Deng, Youquan
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supporting information; experimental part
p. 9391 - 9393
(2012/09/21)
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- KOH-mediated transition metal-free synthesis of imines from alcohols and amines
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The various imines were prepared from alcohols and amines in moderate to good yields under an air atmosphere promoted by KOH, eliminating the need for toxic transition metal catalysts. Due to its simplicity, this protocol will have wide application in synthesis.
- Xu, Jian,Zhuang, Rongqiang,Bao, Lingling,Tang, Guo,Zhao, Yufen
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p. 2384 - 2387
(2013/02/21)
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- NaOH-catalyzed imine synthesis: Aerobic oxidative coupling of alcohols and amines
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The convenient transition-metal-free synthesis of imines through oxidative coupling of alcohols and amines is reported. The reaction is catalyzed by NaOH (10 mol-%) and is performed with air as an oxidant in the absence of any co-solvent. The convenient transition-metal-free synthesis of imines through oxidative coupling of alcohols and amines is reported. The reaction is catalyzed by NaOH (10 mol-%) and is performed with air as an oxidant in the absence of any co-solvent. Copyright
- Donthiri, Ramachandra Reddy,Patil, Rajendra D.,Adimurthy, Subbarayappa
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p. 4457 - 4460
(2012/10/30)
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- Copper-catalyzed highly efficient aerobic oxidative synthesis of imines from alcohols and amines
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A highly efficient and green tandem imine synthesis from alcohol and amine with molecular oxygen as oxidant was achieved by using a remarkable low catalyst-loading, with a commercially available and environmentally benign copper catalyst.
- Kang, Qiang,Zhang, Yugen
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experimental part
p. 1016 - 1019
(2012/06/04)
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- Highly active and selective synthesis of imines from alcohols and amines or nitroarenes catalyzed by Pd/DNA in water with dehydrogenation
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A direct imination was developed from alcohols and amines under catalysis of Pd/DNA by dehydrogenation without additional oxidant, affording the corresponding imines in moderate to good yields with excellent chemoselectivity. By virtue of the liberated molecular hydrogen, the nitroarenes could also be deoxidized in situ into amines and a one-pot tandem synthesis of imines was achieved from nitroarenes. This heterogeneous catalyst can be recovered and reused at least five times by taking advantage of its water-soluble reversibility. All these conformations were performed smoothly in water under mild conditions, and an atom economical and environmentally benign synthesis was embodied in this imination.
- Tang, Lin,Sun, Huayin,Li, Yunfeng,Zha, Zhenggen,Wang, Zhiyong
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p. 3423 - 3428
(2013/01/16)
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- Iron-catalyzed tandem reactions of aldehydes, terminal alkynes, and primary amines as a strategy for the synthesis of quinoline derivatives
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FeCl3-catalyzed three-component tandem condensation/addition/ cyclization/oxidation reactions of aldehydes, terminal alkynes, and primary amines have been developed. The processes can provide a diverse range of quinoline derivatives in good yields from simple starting materials. A possible reaction mechanism was proposed.
- Zhang, Yicheng,Li, Pinhua,Wang, Lei
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experimental part
p. 153 - 157
(2011/03/21)
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- Titanocene(III) chloride mediated radical induced allylation of aldimines: Formal synthesis of C-linked 4′-deoxy aza-disaccharide
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Titanocene(III) chloride (Cp2TiCl) mediated radical induced allylation of aldimines for the preparation of homoallyl amines is described. The radical was generated from the allyl bromide using Cp2TiCl as the radical source. Formal synthesis of C(4)-C(5′)-linked 4′-deoxy aza-disaccharide is demonstrated and a study toward the bicyclic skeleton of alkaloids was also accomplished. The radical initiator Cp2TiCl was prepared in situ from commercially available titanocene dichloride (Cp 2TiCl2) and Zn dust in THF under argon.
- Saha, Sumit,Roy, Subhas Chandra
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experimental part
p. 7229 - 7234
(2011/10/18)
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- Catalyst-free reduction of aldimines with hantzsch esters
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An efficient catalyst-free reduction of aldimines is reported. In the absence of any additional catalysts, a series of N-aromatic aldimines were reduced with Hantzsch esters as the hydrogenation source. Moderate to excellent isolated yields (up to 99 %) were obtained under mild conditions.
- Li, Jianhui,Wang, Zhouyu,Jiang, Zhenju,Jiang, Shengqian,Xiong, Lilin
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experimental part
p. 4101 - 4103
(2012/01/06)
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- Pt-Sn/γ-Al2O3-catalyzed highly efficient direct synthesis of secondary and tertiary amines and imines
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Versatile syntheses of secondary and tertiary amines by highly efficient direct N-alkylation of primary and secondary amines with alcohols or by deaminative self-coupling of primary amines have been successfully realized by means of a heterogeneous bimetallic Pt-Sn/γ-Al2O3 catalyst (0.5 wt % Pt, Pt/Sn molar ratio=1:3) through a borrowing-hydrogen strategy. In the presence of oxygen, imines were also efficiently prepared from the tandem reactions of amines with alcohols or between two primary amines. The proposed mechanism reveals that an alcohol or amine substrate is initially dehydrogenated to an aldehyde/ketone or NH-imine with concomitant formation of a [PtSn] hydride. Condensation of the aldehyde/ketone species or deamination of the NH-imine intermediate with another molecule of amine forms an N-substituted imine which is then reduced to a new amine product by the in-situ generated [PtSn] hydride under a nitrogen atmosphere or remains unchanged as the final product under an oxygen atmosphere. The Pt-Sn/γ-Al2O 3 catalyst can be easily recycled without Pt metal leaching and has exhibited very high catalytic activity toward a wide range of amine and alcohol substrates, which suggests potential for application in the direct production of secondary and tertiary amines and N-substituted imines.
- He, Wei,Wang, Liandi,Sun, Chenglin,Wu, Kaikai,He, Songbo,Chen, Jiping,Wu, Ping,Yu, Zhengkun
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experimental part
p. 13308 - 13317
(2012/02/02)
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- A thermal study of some Schiff bases derivative of α-napthylamine
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Thermal analyses of some Schiff bases, derivative of α-napthylamine, were performed by the DSC, TG and DTA techniques. The thermograms were used to determine various kinetic parameters, such as the order of degradation (n), energy of activation (E), frequ
- Baluja, Shipra,Pandya, Nirmal,Vekariya, Nayan
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experimental part
p. 1601 - 1604
(2009/02/03)
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- Palladium-catalyzed aerobic oxidation of amines
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Pd-Catalyzed aerobic oxidation of different amines was systematically examined for the first time. A PdCl2/PPh3 system was successfully developed to catalyze the aerobic oxidation of several types of amines including Ar-CH2NHPh, Ar-CH2NHOMe, and Ar-CH2NHMs with high yields. Theoretical studies showed a remarkable difference in the energy barriers of β-hydride elimination between an alcohol and various amines.
- Wang, Jia-Rui,Fu, Yao,Zhang, Bei-Bei,Cui, Xin,Liu, Lei,Guo, Qing-Xiang
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p. 8293 - 8297
(2007/10/03)
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- A study of anti-inflammatory activity of some novel α-amino naphthalene and β-amino naphthalene derivatives
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In the present study, some naphthalene derivatives have been synthesized by incorporating azetidinyl and thiazolidinyl moieties at its α- or β-positions such as a-(3-chloro-2-oxo-4-substitute-d)aryl-1-azetidinyl) naphthalenes 6-10, α-((substituted)aryl-4-
- Sharma, Shalabh,Singh, Tripti,Mittal, Rajan,Saxena,Srivastava, Virendra Kishore,Kumar, Ashok
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p. 145 - 152
(2007/10/03)
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- Imino Diels-Alder reactions: an efficient one-pot synthesis of pyrano and furanoquinoline derivatives catalyzed by SbCl3
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Antimony trichloride (SbCl3) was found to be an efficient catalyst for the inverse electron demand imino Diels-Alder reactions of in situ generated N-benzylidenes with 3,4-dihydro-2H-pyran and 2,3-dihydrofuran to afford pyrano and furano[3,2-c]quinolines in excellent yields.
- Maiti, Gourhari,Kundu, Pradip
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p. 5733 - 5736
(2007/10/03)
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- Stereocontrolled synthesis of anticancer β-lactams via the Staudinger reaction
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Stereocontrolled synthesis of novel β-lactams using polyaromatic imines following the Staudinger reaction has been accomplished. The effects of domestic microwave irradiation on this type of reaction have been investigated. Formation of trans-β-lactams has been explained through isomerization of the enolates formed during the reaction of acid chloride (equivalent) with imines in the presence of triethylamine. A donor-acceptor complex pathway is believed to be involved in the formation of cis-β-lactams. The effect of a peri hydrogen has been found to be significant in controlling the stereochemistry of the resulting β-lactams. SAR has identified β-lactams with anticancer activity. The presence of an acetoxy group has proven obligatory for their anticancer activity.
- Banik, Bimal K.,Banik, Indrani,Becker, Frederick F.
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p. 3611 - 3622
(2007/10/03)
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- Synthesis of imines, diimines and macrocyclic diimines as possible ligands, in aqueous solution
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Although it is recognized that the presence of water is disadvantageous for imine synthesis, we demonstrate that such synthesis can be effective in completely aqueous media, without any catalyst and under mild conditions. Thus, arylaryl, aryl-alkyl, alkyl-aryl and alkyl-alkyl monoimines as well as a large variety of diimines are obtained by direct condensation of the corresponding carbonyl compounds and amines, in water. The same process is used to synthesize macrocyclic diimines starting from methylene, ethylene, trimethylene and tetramethylene glycol bis(2-formylphenyl ether) and ethylene-, trimethylene- and tetramethylene-diamine, some of these macrocycles being known for their chelating properties.
- Simion, Alina,Simion, Cristian,Kanda, Tadeshige,Nagashima, Satoko,Mitoma, Yoshiharu,Yamada, Tomoko,Mimura, Keisuke,Tashiro, Masashi
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p. 2071 - 2078
(2007/10/03)
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- CATALYTIC DEHYDROGENATION OF SECONDARY AMINES WITH COBALT SCHIFF BASE COMPLEX-OXYGEN SYSTEM
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Catalytic oxidation of secondary aromatic amines using Co(salen)/O2 in ethanol at 60 degC leads to dehydrogenation of the amines affording the corresponding imines in high yield.A mechanism involving electron transfer from the substrate to cobalt(III) species is suggested.
- Nishinaga, Akira,Yamazaki, Shigekazu,Matsuura, Teruo
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p. 4115 - 4118
(2007/10/02)
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- Synthesis and Spectra of 7-(o- and p-R-Phenyl)-10,10-dimethyl-8,9,10,11-tetrahydrobenzacridin-8-ones. Structure Correction of 1,2,3,4-Tetrahydro-2,2-dimethyl-5-aryl-6-aza-7,8-benzophenanthren-4-ones
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It has been reported that dimedone added to α-arylidennaphthylamines in ethanol with formation of 1,4-addition products derivatives of 5-aryl-5,6,7,8,9,10-hexahydrobenzophenanthridin-7-ones, III, which are easily oxidized by chromic anhydride to the co
- Cortes, Eduardo,Martinez, Roberto,Avila, J. Gustavo,Toscano, R. Alfredo
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p. 895 - 899
(2007/10/02)
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