- Electrochemical Oxidative Cyclization: Synthesis of Polysubstituted Pyrrole from Enamines
-
A conceptually novel method for the preparation of pyrrole is described by electrochemical-oxidation-induced intermolecular annulation via enamines. In a simple undivided cell, based on a sodium acetate-facilitated, polysubstituted pyrrole derivations has been facilely synthesized under external oxidant-free condition. This electrosynthetic approach providing an environmentally benign protocol for C?C bond cross-coupling and oxidative annulation, which features unparalleled broad scope of substrates and practicality.
- Chen, Zhiwei,Shi, Guang,Tang, Wei,Sun, Jie,Wang, Wenxing
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supporting information
p. 951 - 955
(2021/02/03)
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- Cobaloxime Catalysis for Enamine Phosphorylation with Hydrogen Evolution
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Direct phosphorylation of enamine and enamide with hydrogen evolution was realized via cobaloxime catalysis under visible-light irradiation. Control experiments and spectroscopic studies demonstrated a reductive quenching pathway of cobaloxime catalyst to produce phosphinoyl radical, which underwent cross-coupling with various enamines (and enamides) to give diverse β-phosphinoyl products in good to excellent yields. More interestingly, Z/E mixture of acyclic enamines could convert into single Z-products with good reactivity.
- Lei, Tao,Liang, Ge,Cheng, Yuan-Yuan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
-
supporting information
p. 5385 - 5389
(2020/07/08)
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- Copper-Mediated One-Pot Synthesis of Indoles through Sequential Hydroamination and Cross-Dehydrogenative Coupling Reaction
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Starting from simple anilines and ester arylpropiolates, an efficient one-pot synthesis of 2-arylindole-3-carboxylate derivatives has been developed through copper-mediated sequential hydroamination and cross-dehydrogenative coupling (CDC) reaction. The i
- Cai, Yichao,Chen, Chunxia,Chen, Xin,Liu, Yajie,Peng, Jinsong,Song, Zirui,Sun, Peng,Yang, Jiaojiao
-
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- Alkynyl Fischer Carbenes as a Platform for the Production of Difluorodiazaborinine Complexes via β-Amino-azadienes
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The results of a study of the reactivities of alkynyl Fischer carbenes in the syntheses of diazaborinine derivatives 7a-i are reported. The strategy employed included the use of β-amino-α,β-unsaturated carbenes (3a–j) with different amines in order to determine the scope of a previously unknown catalytic reaction in the presence of copper salts and anilines. The reaction was highly stereoselective, yielding (Z)-isomers of the β-amino-1-azadiene framework as the main products (4a–o). As an extension of this research, the compounds 4a–o proved to be suitable precursors for the syntheses of diazaborinine scaffolds in good yields (7a-i).
- Benítez-Puebla, Luis J.,López, Julio,Flores-álamo, Marcos,Cruz, David Cruz,Pe?a-Cabrera, Eduardo,Delgado, Francisco,Tamariz, Joaquín,Vázquez, Miguel A.
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p. 6571 - 6578
(2019/10/22)
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- Catalytic Mechanism Study on the 1,2- and 1,4-Transfer Hydrogenation of Ketimines and β-Enamino Esters Catalyzed by Axially Chiral Biscarboline-Based Alcohols
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Axial N-O alcohols, which have two large carboline moieties connected to the axis were synthesized and used in catalytic enantioselective 1,2- and 1,4-transfer hydrogenations of total 26 ketimines and β-enamino esters. Excellent levels of enantioselectivity ranging from 91% to 99% were achieved by using catalyst (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. Interestingly, a mixture of (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide and (aR)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide was also able to provide high enantioselectivities up to 95% that is the same as that using pure (aS)-(S)-3,3′-bis((S)-2-(hydroxymethyl)pyrrolidine-1-carbonyl)-9,9′-dimethyl-9H,9′H-[1,1′-bipyrido[3,4-b]indole] 2-oxide. A plausible catalytic mechanism was suggested and total four kinds of transition states (TS) including almost 60 TS structures were investigated using density functional theory (DFT) with different basis sets such as 6-311G(2d,p). The predicted activation energy data are consistent with the experimental results. (Figure presented.).
- Dong, Mengxian,Wang, Jie,Wu, Shijie,Zhao, Yang,Ma, Yangyang,Xing, Yongfei,Cao, Fei,Li, Longfei,Li, Zhenqiu,Zhu, Huajie
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supporting information
p. 4602 - 4610
(2019/08/30)
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- Two Distinct Ag(I)- And Au(I)-Catalyzed Olefinations between α-Diazo Esters and N-Boc-Derived Imines
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Metal-catalyzed reactions between α-diazo esters and imines were well-known to yield aziridine derivatives exclusively. This work reports two new olefination reactions between N-Boc-derived (Boc = tert-Butyloxycarbonyl) imines and α-diazo esters with Ag(I) and Au(I) catalysts, respectively. Our mechanistic studies reveal that these new olefinations involve an initial attack of diazo esters on metal/imine complexes to form Mannich-addition intermediates, which subsequently afford α-aryl-β-aminoacrylates via a Roskamp reaction, or to form β-aryl-β-aminoacrylates via the formation of silver carbenes.
- Kardile, Rahul Dadabhau,Liu, Rai-Shung
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supporting information
p. 6452 - 6456
(2019/09/06)
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- Isobutyl Nitrite-Mediated Synthesis of Quinoxalines through Double C?H Bond Amination of N-Aryl Enamines
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An efficient and metal-free double C?H bond amination of N-aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N-aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key β-imino oxime ester intermediate. A quinoxaline derivative could be prepared from β-carbonyl ester in one-pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps. (Figure presented.).
- Jiao, Yan-Xiao,Wei, Lin-Su,Zhao, Chun-Yang,Wei, Kai,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa
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p. 4446 - 4451
(2018/10/20)
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- PIDA/TBAB-Promoted Oxidative Geminal Dibromofunctionalization of Alkynes: Direct Synthesis of Geminal Diazides
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PIDA/TBAB-promoted oxidative geminal diazidofunctionalization of alkynes has been described for the first time. The transformation demonstrates a mechanistically distinctive approach to access geminal diazides, in which TBAB plays a crucial role as brominating agent and for the in situ generation of tetrabutylammonium azide. Furthermore, we have demonstrated here the first cycloaminative strategy by tactically employing the two azides groups leading to quinoxalines and synthesis of bis-triazole derivatives via copper catalysis.
- Arepally, Sagar,Babu, Venkata Nagarjuna,Polu, Ashok,Sharada, Duddu S.
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supporting information
p. 5700 - 5705
(2018/10/15)
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- A sustainable synthesis of 2-aryl-3-carboxylate indolines from N-aryl enamines under visible light irradiation
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With visible light irradiation of a catalytic amount of Ir(ppy)3 at room temperature, a number of N-aryl enamines were transformed into their corresponding indoline products in good to excellent yields without requiring any extra additives. This is the first example of the synthesis of indolines via the intramolecular cyclization of enamines under visible light irradiation.
- Wu, Cheng-Juan,Cao, Wen-Xiao,Lei, Tao,Li, Zhi-Hua,Meng, Qing-Yuan,Yang, Xiu-Long,Chen, Bin,Ramamurthy, Vaidhyanathan,Tung, Chen-Ho,Wu, Li-Zhu
-
supporting information
p. 8320 - 8323
(2017/07/26)
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- Synthesis of Quinoxaline Derivatives via Tandem Oxidative Azidation/Cyclization Reaction of N -Arylenamines
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A new method was developed for the synthesis of quinoxalines. This method employs N-arylenamines and TMSN3 as the starting materials and implements two oxidative C-N bond-forming processes in a tandem pattern by using (diacetoxyiodo)benzene as the common oxidant. The present reaction conditions are mild and simple and thus are useful in practical synthesis. (Chemical Equation Presented).
- Ma, Haichao,Li, Dianjun,Yu, Wei
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supporting information
p. 868 - 871
(2016/03/04)
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- Tandem Copper-Catalyzed Propargylation/Alkyne Azacyclization/Isomerization Reaction under Microwave Irradiation: Synthesis of Fully Substituted Pyrroles
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A copper-catalyzed and microwave-assisted synthesis of fully substituted pyrroles has been developed. A series of pentasubstituted pyrroles, especially α-arylpyrroles, could be obtained in moderate to good yields (up to 93%) through a tandem propargylation/alkyne azacyclization/isomerization sequence from readily available β-enamino compounds and propargyl acetates.
- Zhang, Xiao-Yan,Yang, Zhi-Wei,Chen, Zhongzhu,Wang, Jun,Yang, Dong-Lin,Shen, Ze,Hu, Li-Li,Xie, Jian-Wu,Zhang, Jin,Cui, Hai-Lei
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p. 1778 - 1785
(2016/03/15)
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- Visible Light Initiated Hantzsch Synthesis of 2,5-Diaryl-Substituted Pyrroles at Ambient Conditions
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Irradiation of a mixture of enamines and α-bromo ketones, with a catalytic amount of Ir(ppy)3 by visible light (Λ= 450 nm), enables the production of various 2,5-diaryl-substituted pyrroles in good to excellent yields. The key intermediates in
- Lei, Tao,Liu, Wen-Qiang,Li, Jian,Huang, Mao-Yong,Yang, Bing,Meng, Qing-Yuan,Chen, Bin,Tung, Chen-Ho,Wu, Li-Zhu
-
supporting information
p. 2479 - 2482
(2016/06/09)
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- A copper-mediated oxidative coupling route to 3H- and 1H-indoles from N-aryl-enamines
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A facile copper(II)-mediated C-H bond oxidation and C-C bond formation procedure has been applied to the synthesis of indole derivatives. Intramolecular oxidative coupling of 3,3-disubstituted enamines proceeded using a non-expensive and air-stable copper
- Drouhin, Pauline,Taylor, Richard J. K.
-
supporting information
p. 2333 - 2336
(2015/04/22)
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- Cobalt-catalyzed hydrogenation of β-enamino esters using an internal mixture of bidentate and monodentate ligands
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Different β-amino esters have been obtained in good yields by means of octacarbonyldicobalt-catalyzed hydrogenation of β-enamine esters in the presence of mixture of a bidentate phosphine chiral (R-BINAP) and a monodentate phosphine achiral (PPh3/su
- Amézquita-Valencia, Manuel,Cabrera, Armando
-
supporting information
p. 145 - 150
(2014/08/05)
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- Ag/CNT-catalyzed hydroamination of activated alkynes with aromatic amines
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As a nanoparticle support material, carbon nanotubes (CNTs) provide a certain potential activation of catalysis in heterogeneous catalytic organic reactions. Herein, an efficient Ag/CNT-catalyzed synthesis of enamines via hydroamination of activated alkynes with aromatic amines has been described. This catalyst still retains catalytic activity after being recycled and reused three times. In addition, it represents a green and environmentally friendly process for preparation of enamines. Copyright 2013 John Wiley & Sons, Ltd. Ag/CNTs catalysis has been developed to synthesize enamines via hydroamination of asymmetry alkylnates with aromatic amines. The catalysis can be recycled and reused 3 times, which also remain catalytic activity. In addition, it represents a green and environmentally friendly process for preparation of enamines. Copyright
- Liu, Yi,Wu, Guojie,Cui, Yingde
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p. 206 - 208
(2013/06/05)
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- Synthesis of chiral β-amino acid derivatives by asymmetric hydrosilylation with an imidazole derived organocatalyst
-
The organocatalysed asymmetric hydrosilylation of a number of N-aryl and alkyl β-substituted enamino esters proceeds in generally good yield and enantioselectivity. Crucial to obtaining high yield and selectivity was the addition of benzoic acid as an additive and under these conditions, both N-alkyl and N-aryl substituents were well tolerated. β-Aryl and alkyl substituents were evaluated and a model proposed to account for the experimental observations based upon enamine tautomerisation and conformational preferences of the reactive ketimine intermediate.
- Jones, Simon,Li, Xianfu
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experimental part
p. 5522 - 5532
(2012/09/21)
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- Cross-dehydrogenative coupling between enamino esters and ketones: Synthesis of tetrasubstituted pyrroles
-
Tetrasubstituted pyrroles have been synthesized via the cross-dehydrogenative coupling between enamino esters and acetone. Silver carbonate proved to be an effective oxidant, and no transition metal catalyst is necessary.
- Zhao, Miao,Wang, Fen,Li, Xingwei
-
supporting information; experimental part
p. 1412 - 1415
(2012/05/04)
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- Tandem transformations of nitriles into N-heterocyclic compounds by electrophilic trapping of Blaise reaction intermediates
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Tandem transformations of nitriles into various N-heterocycles have been accomplished through the reaction of electrophiles with Blaise reaction intermediates formed in situ. The reaction of the Blaise reaction intermediates with propiolates gives 2-pyridones through consecutive C- and N-nucleophilic reactions. The tandem reactions of the Blaise reaction intermediate with 1,3-enynes proceed through C-nucleophilic addition followed by an electrocyclization-aromatization cascade to give pyridines. Exocyclic enamino esters can be prepared by transformations of ω-chloroalkyl nitriles through chemoselective intramolecular alkylation of the Blaise reaction intermediate. Palladium-catalyzed intramolecular arylations or copper-catalyzed intermolecular cross-coupling reactions of the Blaise reaction intermediate give a range of indole derivatives. Combinations of tandem alkylations and palladium-catalyzed couplings of the Blaise reaction intermediates of ω-chloroalkyl nitriles give N-fused indoles. Georg Thieme Verlag Stuttgart · New York.
- Kim, Juhyun,Chun, Yusung,Shin, Hyunik,Lee, Sang-Gi
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scheme or table
p. 1809 - 1817
(2012/08/08)
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- Tandem one-pot construction of indoles via palladium and copper-catalyzed coupling reactions of the blaise reaction intermediate
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The palladium-catalyzed intramolecular N-arylation of the Blaise reaction intermediate, formed by reaction of nitriles with an in situ generated Reformatsky reagent from ethyl -bromo - (2-bromophenyl)acetate and zinc, afforded indoles in good yields. Exte
- Kim, Ju Hyun,Lee, Sang-Gi
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experimental part
p. 1464 - 1476
(2012/09/08)
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- I2-catalyzed indole formation via oxidative cyclization of N-aryl enamines
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Cat.'s Is: An I2-catalyzed synthesis of indoles, taking advantage of intramolecular dehydrogenative coupling reactions of enamines, afforded a variety of multifunctionalized indole derivatives in good to excellent yields under transition-metal-
- He, Zhiheng,Liu, Weiping,Li, Zhiping
-
supporting information
p. 1340 - 1343
(2013/01/11)
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- Cyanuric chloride catalysed rapid conversion of β-ketoesters into β-enaminoesters under mild and solvent-free conditions
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Cyanuric chloride is shown to be an extremely efficient catalyst for the synthesis of β-enaminoesters from β-ketoesters under solvent-free conditions by grinding in a mortar with pestle at 25 °C. A short reaction time, an inexpensive and easily available catalyst, mild reaction conditions and excellent yields of the products are attractive features of this methodology.
- Kamble,Joshi,Atkore
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experimental part
p. 616 - 621
(2012/07/03)
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- A facile, chemoselective and eco-friendly solid phase synthesis of enaminones catalyzed by L-Proline
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A facile and chemoselective method for the synthesis of enaminones by the reaction of aromatic primary amines with various β-ketoesters in the presence of L-proline as activator under solid phase is described. The reactions are promoted by the catalyst in short time (5-6 min) under ambient conditions, without any side products.
- Bhupathi, Raja S.,Devi, B.Rama,Dubey
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experimental part
p. 5521 - 5524
(2012/07/13)
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- Microwave-assisted synthesis of polysubstituted 4-quinolones from deprotonated α-aminonitriles
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The α-alkylation of deprotonated N-aryl-α-aminonitriles with α-bromoesters furnishes intermediates that can be cyclized to 4-quinolones upon microwave irradiation. Alternatively, base-induced dehydrocyanation of the alkylation products furnishes enaminoes
- Romek, Alexandra,Opatz, Till
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experimental part
p. 5841 - 5849
(2011/01/04)
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- Hydrogenation of β-N-substituted and β-N,N-disubstituted enamino esters in the presence of iridium(I) catalyst
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Several new β-amino esters were prepared in two simple steps from β-keto ester derivatives and primary and secondary amines under mild conditions. The hydrogenation of various enamino esters was performed at 50°C in the presence of iridium catalysts. The new β-N-substituted amino esters were isolated in high yields. Georg Thieme Verlag Stuttgart.
- Hebbache, Hania,Hank, Zakia,Bruneau, Christian,Renaud, Jean-Luc
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experimental part
p. 2627 - 2633
(2009/12/06)
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- Palladium-catalyzed oxidative cyclization of N-aryl enamines: From anilines to indoles
-
(Chemical Equation Presented) The special advantage of the title reaction to form substituted indoles 2 lies within the broad scope of the transformation: A multitude of N-aryl enaminones 1 can be prepared readily in one step from commercially available anilines. Furthermore, anilines can be converted directly in a one-pot process into the indole products. R1 = H, Me, OMe, Cl, F, carbonyl functionality, CN, fused aryl; R2 = alkyl, aryl; R 3 = alkyl, O-alkyl.
- Wuertz, Sebastian,Rakshit, Souvik,Neumann, Julia J.,Droege, Thomas,Glorius, Frank
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supporting information; experimental part
p. 7230 - 7233
(2009/04/10)
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- Development, scope and mechanisms of multicomponent reactions of asymmetric electron-deficient alkynes with amines and formaldehyde
-
Based on the reactive behaviour of the substrates, two synthetic routes to polysubstituted pyrimidine derivatives are presented herein: 1) A catalyst-free multicomponent reaction of electron-deficient alkynes, aliphatic amines and formaldehyde and 2) Ag1catalyzed synthesis of pyrimidines from electron-deficient alkynes, anilines and formaldehyde by a domino reaction. Under optimized conditions, the multicomponent reactions were accomplished with high regioselectivity and excellent yields. A computational study was carried out by using the B3LYP density functional theory to elucidate the mechanisms of the catalyst-free hydroamination reaction. Calculations showed the activation free energies of aliphatic amines were lower than those of anilines, which is consistent with the experimental results.
- Cao, Hua,Wang, Xiujun,Jiang, Huanfeng,Zhu, Qiuhua,Zhang, Min,Liu, Haiyang
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scheme or table
p. 11623 - 11633
(2009/12/07)
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- Divergent pathways in the reaction of fischer carbenes and palladium
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The Pd-catalyzed reaction of β-arylaminochromium(0) carbene complexes produces by transmetalation the first isolated and X-ray structurally characterized bis-Pd(II) carbene complex, as well as other alternative reaction pathways, such as the oxidative addition-transmetalation sequence, not seen before in this chemistry.
- Lopez-Alberca, Maria P.,Mancheno, Maria J.,Fernandez, Israel,Gomez-Gallego, Mar,Sierra, Miguel A.,Torres, Rosario
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p. 1757 - 1759
(2008/02/02)
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- VCl3 catalysed efficient synthesis of β-enamine esters and ketones from β-keto esters
-
VCl3 is a useful and efficient catalyst for the synthesis of β-enamine esters and ketones from β-keto esters with primary amines.
- Rajitha, Bavanthula,Reddy, Penthala Narsimha,Kumar, Buridapad Sunil,Srinivasulu, Neeladri,Reddy, Yerram Reddy Thirupathi
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p. 535 - 536
(2007/10/03)
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- Efficient synthesis of β-aminoacrylates and β-enaminones catalyzed by Zn(OAc)2·2H2O
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The direct condensation of amines with β-ketoesters and β-diketones to produce functional enamine derivatives has been investigated with zinc Lewis acid catalysts. Zn(OAc)2·2H2O shows good catalytic activity and leads to a chemo- and stereoselective formation of (Z)-enamine derivatives from aliphatic primary amines and ring-substituted anilines under mild conditions.
- Vohra, Ramandeep Kaur,Renaud, Jean-Luc,Bruneau, Christian
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p. 1943 - 1952
(2007/10/03)
-
- Efficient rhodium-catalyzed asymmetric hydrogenation for the synthesis of a new class of N-aryl β-amino acid derivatives
-
(Chemical Equation Presented) N-Aryl β-amino esters were obtained by asymmetric hydrogenation of a new class of N-aryl β-enamino esters. High conversions and up to 96.3% ee values were achieved with a Rh-TangPhos catalyst.
- Dai, Qian,Yang, Weiran,Zhang, Xumu
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p. 5343 - 5345
(2007/10/03)
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- PYRIDIN-4-YLAMINE COMPOUNDS USEFUL IN THE TREATMENT OF NEUROPATHIC PAIN
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The present invention is directed to a method of use of triazolo-pyridazine compounds in the treatment of neuropathic pain. The present invention is also directed to the use of triazolo-pyridazine compounds in the treatment of psychiatric and mood disorde
- -
-
Page/Page column 45
(2010/02/11)
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- Synthesis of asymmetric iron-pybox complexes and their application to aziridine forming reactions
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The synthesis of a series of iron-pybox complexes and their employment in the catalytic asymmetric aziridine forming reaction is presented. When AgSbF6 is used as an initiator, the i-pr- and t-bu-pybox complexes produce 47% of the cis-aziridine
- Redlich, Mark,Hossain, M. Mahmun
-
p. 8987 - 8990
(2007/10/03)
-
- Synthesis of aziridines from imines and ethyl diazoacetate in room temperature ionic liquids
-
The synthesis of aziridines from imines and ethyl diazoacetate in room temperature ionic liquids is reported. The reactions proceed readily under mild conditions with high cis selectivities and high yields.
- Sun, Wei,Xia, Chun-Gu,Wang, Hong-Wang
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p. 2409 - 2411
(2007/10/03)
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- An explanation for the apparent cis-aziridine selectivity in the iron Lewis acid-catalyzed reaction of N-benzylidene aniline and ethyl diazoacetate
-
The reason for the apparent cis-aziridine selectivity in the reaction of ethyl diazoacetate with N-benzylidene aniline, catalyzed by [(η5-C5H5)(CO)2Fe(THF)] +[BF4]-, is reported. The catalytic reaction produces both cis and trans-aziridines. Once the imine has been consumed, the trans-isomer is shown to undergo a catalytic decomposition, leaving cis-aziridine and by-products. The reaction is graphically profiled to illustrate the relative quantity of reactants and products as a function of time. A new mechanistic model is proposed in order to explain the observed selectivity.
- Mayer, Michael F.,Wang, Qinwei,Hossain, M. Mahmun
-
-
- InCl3 catalyzed reactions of ethyl diazoacetate with aldimines: A highly diastereoselective synthesis of cis-aziridine carboxylates
-
InCl3 catalyzed reactions of ethyl diazoacetate with aldimines give aziridine carboxylates under mild conditions, low catalyst loading and with high cis-selectivity. (C) 2000 Elsevier Science Ltd.
- Sengupta,Mondal
-
p. 6245 - 6248
(2007/10/03)
-
- Aziridine synthesis in protic media by using lanthanide triflates as catalysts
-
Ln(OTf)3-catalyzed aziridine synthesis from imines and diazo compounds was studied in a variety of protic media. The reactions proceeded readily under mild conditions and were highly selective, affording predominantly cis aziridines. The imines used were typically those derived from aromatic aldehydes and aromatic amines, with either electron-donating or electron- withdrawing substituents. N-benzyl aryl aldimines and imines derived from aromatic amines and hindered aliphatic aldehydes were also found to work well. Among the three diazo compounds examined, ethyl diazoacetate (EDA) and 3-nitrophenyl diazomethane were effective reagents for the aziridination. However, the reactions of ethyl diazoacetoacetate failed to give any desired product. Six lanthanides triflates as well as Sc(OTf)3 and Y(OTf)3 were tested as catalyst in the aziridination reaction. The formation of the by- products was also discussed.
- Xie, Wenhua,Fang, Jianwen,Li, Jun,Wang, Peng George
-
p. 12929 - 12938
(2007/10/03)
-
- Catalytic preparation of aziridines with an iron lewis acid
-
The iron Lewis acid, [(;75-C5H5)Fe(CO)2(THF)]+[BF4]-) was found to be an effective catalyst for the preparation of aziridines. This new method provides a facile, one-step route to predominantly cisaziridines, with yields up to 95%, from compounds with a diazo functionality and a variety of substituted AT-benzylidene imines with N-aryl or AT-alkyl groups. The reaction mechanism is believed to proceed through an electrophilic iminium ion intermediate. To support this idea, the iron Lewis acid-imine complex [(?75-C5H5)Fe(CO)2(PhCH=NPh)]+[BF.j]- was prepared, characterized, and reacted with different diazo compounds to provide the resultant czs-aziridines. Alternatively, it may be possible that the aziridines were derived from an electrophilic carbenoid intermediate, as is often proposed. Thus, the iron carbene [(2-CsIWFeCCOMCHPhOl+LSOaCFg]- was prepared and treated with AT-benzylideneaniline; however, the resultant aziridine was not formed.
- Mayer, Michael F.,Mahmun Hossain
-
p. 6839 - 6844
(2007/10/03)
-
- Facile synthesis of aziridines from imines and diazoesters or aldehydes, amines, and diazoesters using a catalytic amount of lanthanide triflate
-
In the presence of a catalytic amount of lanthanide triflate (Ln(OTf)3), imines reacted with ethyl diazoester in hexane at room temperature to afford the corresponding aziridines in high yields with high diastereoselectivities. Based on these r
- Nagayama, Satoshi,Kobayashi, Shu
-
p. 685 - 686
(2007/10/03)
-
- Synthesis and structure-activity relationships of 9-substituted acridines as endothelin-A receptor antagonists
-
Screening of a compound library against endothelin receptors (ET(A) and ET(B)) revealed PD 102566 (compound 1) as an ET(A) selective antagonist. Synthesis and structure-activity relationships (SAR) of a series of analogs are described.
- Cheng,Lee,Klutchko,Winters,Reynolds,Welch,Flynn,Doherty
-
p. 2999 - 3002
(2007/10/03)
-
- Synthesis and cytotoxicity of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-quinolones and related compounds: Identification as antimitotic agents interacting with tubulin
-
A series of 1,6,7,8-substituted 2-(4'-substituted phenyl)-4-quinolones and related compounds have been synthesized and evaluated as cytotoxic compounds and as antimitotic agents interacting with tubulin. The 2-phenyl-4-quinolones (22-30) with substituents
- Kuo,Lee,Juang,Lin,Wu,Chang,Lednicer,Paull,Lin,Hamel,Lee
-
p. 1146 - 1156
(2007/10/02)
-
- Dioxopyrrolines. XXVII. Syntheses of 2-Aryl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-diones
-
2-Aryl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-diones (3) were easily prepared in good yields by condensation of enamino-esters (2) with oxalyl chloride.The products were characterized by ultraviolet and infrared spectroscopy. Keywords - Δ2-pyrroline-4,5-dione; dioxopyrroline; enamino-ester; ethyl 3-aryl-3-aminopropenoate; 2-aryl-3-ethoxycarbonyl-Δ2-pyrroline-4,5-dione; UV; restricted rotation
- Sano, Takehiro,Horiguchi, Yoshie,Toda, Jun,Imafuku, Kazue,Tsuda, Yoshisuke
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p. 497 - 503
(2007/10/02)
-