- Selective reductive annulation reaction for direct synthesis of functionalized quinolines by a cobalt nanocatalyst
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Due to the extensive applications of quinolines, the search for selective construction of such products has long been an attractive subject in scientific community. Herein, by developing a new N-doped ZrO2@C supported cobalt nanomaterial, it has been successfully applied as an efficient catalyst for the reductive annulation of 2-nitroaryl carbonyls with alkynoates and alkynones. The catalytic transformation allows synthesizing a wide array of funcitonalized quinolines with the merits of broad substrate scope, good functional group tolerance, excellent hydrogen transfer selectivity, reusable earth-abundant metal catalyst, and operational simplicity. The developed chemistry paves the ways for further design of hydrogen transfer-mediated coupling reactions by developing heterogeneous catalysts with suitable supports.
- Xie, Rong,Lu, Guang-Peng,Jiang, Huan-Feng,Zhang, Min
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p. 239 - 243
(2020/02/15)
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- Diethyloxalate as “CO” Source for Palladium-Catalyzed Ethoxycarbonylation of Bromo- and Chloroarene Derivatives
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Palladium(II)-catalyzed ethoxycarbonylation of aryl bromides with diethyloxalate oxalate is described. Functionalized aromatic esters can be efficiently synthesized with only 0.65 mol % PdCl2(PPh3)2 catalyst under microwav
- Monrose, Amandine,Salembier, Helori,Bousquet, Till,Pellegrini, Sylvain,Pélinski, Lydie
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supporting information
p. 2699 - 2704
(2017/08/16)
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- Polythiophene-Encapsulated Bimetallic Au-Fe3O4 Nano-Hybrid Materials: A Potential Tandem Photocatalytic System for Nondirected C(sp2)-H Activation for the Synthesis of Quinoline Carboxylates
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Hetero-oligophenylene derivative 3 appended with thiophene moieties has been designed and synthesized which undergoes aggregation to form J-type fluorescent aggregates in in H2O/THF (7/3) media. These aggregates served as reactors for the preparation of bimetallic Au-Fe3O4 NPs. During the reduction process, aggregates of derivative 3 were oxidized to the polythiophene species 4. Interestingly, the polythiophene species 4, having a fibrous morphology, served as a shape- and morphology-directed template for assembly of bimetallic Au-Fe3O4 NPs in a flower-like arrangement. Furthermore, polythiophene-encapsulated bimetallic 4:Au-Fe3O4 nanohybrid materials served as an efficient and recyclable catalytic system for C(sp2)-H bond activation of unprotected electron-rich anilines for the construction of synthetically versatile quinoline carboxylates via C-H activation, carbonylation, and subsequent annulation under mild and eco-friendly conditions (aqueous media, room temperature, visible-light irradiation, and aerial conditions).
- Kaur, Mandeep,Pramanik, Subhamay,Kumar, Manoj,Bhalla, Vandana
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p. 2007 - 2021
(2017/08/17)
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- 5-AMINO-4-CARBAMOYL-PYRAZOLE COMPOUNDS AS SELECTIVE AND IRREVERSIBLE T790M OVER WT-EGFR KINASE INHIBITORS AND USE THEREOF????
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Disclosed are compounds of Formula (I), pharmaceutical compositions comprising the same, processes for the preparation thereof, and the use thereof.
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Paragraph 0143
(2016/03/13)
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- Acid Chloride Synthesis by the Palladium-Catalyzed Chlorocarbonylation of Aryl Bromides
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We report a palladium-catalyzed method to synthesize acid chlorides by the chlorocarbonylation of aryl bromides. Mechanistic studies suggest the combination of sterically encumbered PtBu3 and CO coordination to palladium can rapidly equilibrate the oxidative addition/reductive elimination of carbon-halogen bonds. This provides a useful method to assemble highly reactive acid chlorides from stable and available reagents, and can be coupled with subsequent nucleophilic reactions to generate new classes of carbonylated products. The Good, the Bad and the Bulky! By employing a sterically encumbered phosphine ligand, tri-tert-butyl phosphine, under palladium catalysis inert aryl bromides are chlorocarbonylated to create reactive acid chlorides by reversible carbon-halogen bond reductive elimination. This general platform allows for an expanded scope of the Heck carbonylation reaction to include previously incompatible nucleophiles.
- Quesnel, Jeffrey S.,Kayser, Laure V.,Fabrikant, Alexander,Arndtsen, Bruce A.
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supporting information
p. 9550 - 9555
(2015/06/30)
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- Copper-catalyzed domino SN2′/coupling reaction: A versatile and facile synthesis of cyclic compounds from baylis-hillman acetates
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A variety of substituted quinoline/pyridine, thiochromene and naphthalene derivatives, which might be of biological and medicinal value, were synthesized by copper-catalyzed domino SN2′/coupling, SN2′ /deacylation/coupling and SN2′/coupling/elimination reactions. The method provides a general and convenient approach to the synthesis of various substituted cyclic compounds from the corresponding Baylis-Hillman (B-H) acetates and N-/S-/C-nucleophiles. Copyright
- Niu, Qingsheng,Mao, Hui,Yuan, Guodong,Gao, Jilong,Liu, Haiquan,Tu, Yawei,Wang, Xiaoxia,Lv, Xin
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supporting information
p. 1185 - 1192
(2013/05/22)
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- Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process
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A convenient synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters via a domino process is described. The synthesis employs arylmethyl azides as the precursor which undergoes an acid-promoted rearrangement to give an N-aryl iminium ion. Following the addition with ethyl 3-ethoxyacrylate, intramolecular electrophilic aromatic substitution, elimination and subsequent oxidation, the quinoline products were obtained in moderate to excellent yields.
- Tummatorn, Jumreang,Thongsornkleeb, Charnsak,Ruchirawat, Somsak,Gettongsong, Tanita
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supporting information
p. 1463 - 1467
(2013/05/08)
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- Iodine-mediated intramolecular electrophilic aromatic cyclization in allylamines: A general route to synthesis of quinolines, pyrazolo[4,3-b] pyridines, and thieno[3,2-b]pyridines
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An unprecedented synthesis of aromatic ring annulated pyridines from suitably substituted primary allylamines via intramolecular electrophilic aromatic cyclization mediated by molecular iodine under mild conditions is described.
- Batchu, Harikrishna,Bhattacharyya, Soumya,Batra, Sanjay
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supporting information
p. 6330 - 6333
(2013/02/23)
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- Using Morita-Baylis-Hillman acetates of 2-azidobenzaldehydes for the synthesis of 2-alkoxy-3-cyanomethylquinolines and alkyl quinoline-3-carboxylates
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Figure represented. A simple method for the synthesis of several 2-alkoxy-3-cyanomethylquinolines and alkyl quinoline-3-carboxylates using iminophosphorane-mediated cyclization reactions of 3-(2-azidophenyl)-2- cyanomethylpropenoates and 3-(2-azidophenyl)-2-nitromethylpropenoates has been developed. These compounds were readily obtained from the Morita-Baylis-Hillman acetates of 2-azidobenzaldehydes using potassium cyanide or sodium nitrite, respectively. J. Heterocyclic Chem., (2011)
- Kim, Hea Jung,Jeong, Eun Mi,Lee, Kee-Jung
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p. 965 - 972
(2011/10/04)
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- A one-step synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid esters from o -nitrobenzaldehydes
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A straightforward and efficient one-step procedure for the synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters is described. The simple reductive cyclization is carried out by treating various substituted o-nitrobenzaldehydes with inex
- Venkatesan, Hariharan,Hocutt, Frances M.,Jones, Todd K.,Rabinowitz, Michael H.
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supporting information; experimental part
p. 3488 - 3491
(2010/08/03)
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- BETA-SECRETASE MODULATORS AND METHODS OF USE
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The present invention comprises a new class of compounds useful for the modulation of Beta-secretase enzyme activity and for the treatment of Beta-secretase mediated diseases, including Alzheimer's disease (AD) and related conditions. In one embodiment, the compounds have a general Formula I wherein A, B, R3, R4, R5, i and j are defined herein. The invention also comprises pharmaceutical compositions including one or more compounds of Formula I, methods of use for these compounds, including treatment of AD and related diseases, by administering the compound(s) of Formula I, or compositions including them, to a subject. The invention also comprises further embodiments of Formulas II and III, intermediates and processes useful for the preparation of compounds of the invention.
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Page/Page column 100
(2010/11/27)
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- Synthesis of quinolines from the Baylis-Hillman acetates via the oxidative cyclization of sulfonamidyl radical as the key step
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Ethyl 3-quinolinecarboxylates 5 were synthesized in good to moderate yields from the Baylis-Hillman acetates 1 via the oxidative cyclization reaction of the N-tosylamidyl radical, which was generated from the rearranged tosylamide derivatives 2 by iodoben
- Kim, Jae Nyoung,Chung, Yun Mi,Im, Yang Jin
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p. 6209 - 6211
(2007/10/03)
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- Synthesis of 3-quinolinecarboxylic acid esters from the Baylis-Hillman adducts of 2-halobenzaldehyde N-tosylimines
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3-Quinolinecarboxylic acid ethyl esters 4 were prepared from 1, the Baylis-Hillman adducts of o-halobenzaldehyde N-tosylimines, in a one-pot reaction.
- Kim, Jae Nyoung,Lee, Hong Jung,Lee, Ka Young,Kim, Hyoung Shik
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p. 3737 - 3740
(2007/10/03)
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- A NOVEL PHOTO-INDUCED SUBSTITUTION OF ALKYL 2-CYANO-3-QUINOLINECARBOXYLATES
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Irradiation of 2-quinolinecarbonitriles having an alkoxycarbonyl group at the 3-position afforded five-membered and/or six-membered lactones in normal alcohols depending on their alkyl-chain-length, whereas the irradiation in 2-propanol and t-butyl alcohol did not cause any cyclization, but instead decyanated and methylated products were obtained, respectively.
- Ono, Isao,Fujiki, Yoshiyuki,Fujinami, Naoki,Hoshi, Toshihiko
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p. 371 - 374
(2007/10/02)
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- Photochemical Reaction of Ethoxycarbonyl-Substituted Quinolines
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The photochemical reactions of the quinoline derivatives substituted by an ethoxycarbonyl group at the 2-, 3-, and 4-positions of a quinoline nucleus have been investigated in several alcohols and cyclohexane.Irradiation of ethyl 4-quinolinecarboxylate (1) yielded ethyl 2-hydroxyalkyl-4-quinolinecarboxylates (4a-c) in alcohols and ethyl 2-cyclohexyl-4-quinolinecarboxylate (4d) in cyclohexane in a good yield, respectively.The photochemical reactions of ethyl 3-quinolinecarboxylate (2) showed remarkable solvent dependency.Irradiation in methanol and cyclohexane afforded a solvent-additive product, ethyl 4-hydroxymethyl-1,4-dihydro-3-quinolinecarboxylate (5a) and ethyl 4-cyclohexyl-1,4-dihydro-3-quinolinecarboxylate (5b), while such photoaddition of the solvent did not proceed in ethanol and 2-propanol but instead ethyl 1,4-dihydro-3-quinolinecarboxylate (6) and dimeric compounds were formed, both of which were unstable and finally reverted to 2 at room temperature in air.In the case of ethyl 2-quinolinecarboxylate two types of the products, ethyl 4-hydroxyalkyl-1,4-dihydro-2-quinolinecarboxylate (7) and ethyl 1,4-dihydro-2-quinolinecarboxylate (8) were obtained in ethanol and 2-propanol but the yields of those products were poor.On the basis of triplet quenching experiments, the photochemical reactions of those ethyl quinolinecarboxylates are suggested to occur through hydrogen abstraction from the solvents by the ring nitrogen in the S1 state.
- Ono, Isao,Hata, Norisuke
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p. 2891 - 2898
(2007/10/02)
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