- One-pot, three-component synthesis of polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridine and benzo[g]pyrazolo[3,4-b]quinoline derivatives in the presence of silver nanoparticles (AgNPs)
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An efficient and straightforward protocol for one-pot, three-component reaction of aryl glyoxal monohydrates 1a-h, 5-amino-1-aryl-3-methylpyrazoles 2a,b and 4-hydroxyquinoline-2(1H)-one (3) or 2-hydroxy-1,4-naphthoquinone (4) using silver nanoparticles (AgNPs) as a high performance nanocatalyst in H2O/EtOH at 60°C afforded the corresponding polyfunctionalized benzo[h]pyrazolo[3,4-b][1,6]naphthyridines 5a-h and benzo[g]pyrazolo[3,4-b]quinolines 6a-i, respectively. Excellent catalytic activity, high yields, employing green media and green nanocatalyst, cost-effective and simple procedure are some notable advantages of using AgNPs as a noble metal nanocatalyst in this synthetic strategy. The structures of fused heterocycles were confirmed by their Fourier transform infrared, proton nuclear magnetic resonance (1H-NMR), and 13C-NMR spectral data and microanalysis.
- Khalafy, Jabbar,Majidi Arlan, Fatemeh,Poursattar Marjani, Ahmad,Sarchami, Vahid
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p. 3961 - 3969
(2020/09/01)
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- Series of Functionalized 5-(2-Arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1 H,3 H)-diones: A Water-Mediated Three-Component Catalyst-Free Protocol Revisited
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A water-mediated and catalyst-free practical method for the synthesis of a new series of pharmaceutically interesting functionalized 5-(2-arylimidazo[1,2-a]pyridin-3-yl)pyrimidine-2,4(1H,3H)-diones has been accomplished based on a one-pot multicomponent reaction between arylglyoxal monohydrates, 2-aminopyridines/2-aminopyrimidine, and barbituric/N,N-dimethylbarbituric acids under reflux conditions. The salient features of this protocol are avoidance of any additive/catalyst and toxic organic solvents, use of water as reaction medium, clean reaction profiles, operational simplicity, ease of product isolation/purification without the aid of tedious column chromatography, good to excellent yields, and high atom-economy and low E-factor.
- Brahmachari, Goutam,Nayek, Nayana,Karmakar, Indrajit,Nurjamal, Khondekar,Chandra, Swapan K.,Bhowmick, Anindita
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p. 8405 - 8414
(2020/07/16)
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- Preparation methods of aprepitant impurity
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The invention discloses preparation methods of an aprepitant impurity, which comprise isomer impurity synthesis method of six aprepitant key intermediates (2R, 3S)-2-[(1R)-1-[3, 5-bis (trifluoromethyl)-phenyl] ethoxy]-3-(4-fluorophenyl) morpholine, respectively, synthesis of four diastereomer impurities, synthesis of one enantiomer impurity and synthesis of one by-product impurity. The methods have the beneficial effects that the five synthesis methods are simple and feasible, the raw materials are easy to obtain, the conditions are mild, the cost is low, the production is facilitated, and meanwhile, the isomer impurities of the synthesized aprepitant key intermediate provide a new intermediate raw material for the preparation of aprepitant.
- -
-
Paragraph 0105; 0109
(2020/07/13)
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- Synthesis of Ethyl 2-Amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates by a One-pot, Three-Component Reaction in the Presence of TPAB
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In this research, in order to synthesize a series of ethyl 2-amino-4-benzoyl-5-oxo-5,6-dihydro-4H-pyrano[3,2-c]quinoline-3-carboxylates, a green and an efficient method is proposed through one-pot three-component reaction of substituted arylglyoxals, ethyl cyanoacetate, and 4-hydroxyquinolin-2(1H)-one in the presence of terapropylammonium bromide as a catalyst in good yields. All synthesized new substances were characterized by FTIR, 1H-NMR, and 13C-NMR spectral data and elemental analysis.
- Poursattar Marjani, Ahmad,Khalafy, Jabbar,Farajollahi, Ayda
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p. 268 - 274
(2018/11/30)
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- A simple protocol for the green synthesis of a new series of pyrimido[4,5b][1,6]naphthyridines in the presence of silver nanoparticles (AgNPs)
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Eight polyfunctionalized pyrimidonaphthyridine derivatives has been synthesized, in 79-92% yields, via the one-pot, three-component reaction of aryl glyoxal monohydrates, 6-aminouracil and 4-hydroxyquinolin-2(1H)-one in H2O/EtOH in the presence of AgNPs under mild conditions. In this work colloidal AgNPs acts as an efficient, economical, green nanocatalyst, leading to a simple method of preparation.
- Marjani, Ahmad Poursattar,Khalafy, Jabbar,Arlan, Fatemeh Majidi,Eyni, Elham
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- Pyridinylimidazoles as GSK3β Inhibitors: The Impact of Tautomerism on Compound Activity via Water Networks
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Glycogen synthase kinase-3β (GSK3β) is involved in many pathological conditions and represents an attractive drug target. We previously reported dual GSK3β/p38α mitogen-activated protein kinase inhibitors and identified N-(4-(4-(4-fluorophenyl)-2-methyl-1
- Heider, Fabian,Pantsar, Tatu,Kudolo, Mark,Ansideri, Francesco,De Simone, Angela,Pruccoli, Letizia,Schneider, Taiane,Goettert, Marcia Inês,Tarozzi, Andrea,Andrisano, Vincenza,Laufer, Stefan A.,Koch, Pierre
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supporting information
p. 1407 - 1414
(2019/10/11)
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- A Facile and Effective Procedure for Synthesis of Polyfunctionalized Bis (imidazolyl) Pyrrole/Imidazolyl Indole from Pyrrole/Indole with Arylglyoxals and N-aryl amidines
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Heterocyclic systems containing bis (imidazolyl) pyrrole or imidazolyl indole moieties were synthesized by heterocyclization of pyrrole or indole with arylglyoxal monohydrates and N-aryl amidines in ethanol catalyzed by FeCl3 at room temperature. The paper reports a facile, efficient, and environmentally friendly protocol for the synthesis of new products. Products were isolated by simple filtration, and their structures were established from their spectroscopic data.
- Masoudi, Mozhgan,Shahbazi-Manshadi, Mohammad Reza,Anary-Abbasinejad, Mohammad
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p. 2772 - 2778
(2019/11/03)
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- One-pot three-component synthesis of a series of 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]pyridine-5-carbonitriles in the presence of aluminum oxide as a nanocatalyst
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[Figure not available: see fulltext.] One-pot three-component reaction of arylglyoxals, 3-aryl-3-oxopropanenitriles, and 5-amino-1-aryl-3-methylpyrazoles using various solvent systems and different catalysts under reflux conditions afforded the corresponding 4-aroyl-1,6-diaryl-3-methyl-1H-pyrazolo[3,4-b]- pyridine-5-carbonitrile derivatives. The best yields (70–91%) were obtained using Al2O3 as a nanocatalyst in H2O–EtOH, 1:1, under reflux conditions. The simplicity of workup procedure, the novelty of pyrazolopyridines, green solvent system, easy preparation of a nanocatalyst, and good to excellent yields of the products are the advantages of this synthetic strategy. The structures of all products were confirmed by FT-IR, 1H and13C NMR, and mass spectral data.
- Arlan, Fatemeh Majidi,Khalafy, Jabbar,Maleki, Ramin
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- Gabapentin-base synthesis and theoretical studies of biologically active compounds: N-cyclohexyl-3-oxo-2-(3-oxo-2-azaspiro[4.5] decan-2-yl)-3-arylpropanamides and N-(tert-butyl)-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)-2-arylacetamide derivatives
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An intermolecular Ugi reaction of 2-(1-(aminomethyl)cyclohexyl)acetic acid (gabapentin) with glyoxal and cyclohexyl isocyanide or aromatic aldehyde and tertbutyl isocyanide under mild conditions in ethanol have been developed to produce two novel class of N-cyclohexyl-3-(aryl)-3-oxo-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)propanamideins and N-(tert-butyl)-2-(3-oxo-2-azaspiro[4.5]decan-2-yl)-2-arylacetamide derivatives in good to excellent yields. This presents the first report for the intermolecular Ugi three component reaction of gabapentin, glyoxal, and an isocyanide. Also according to the theoretical studies the electron-donating groups increase the strength of intramolecular hydrogen bond and electron-withdrawing groups decrease the strength of intramolecular hydrogen bond.
- Amirani Poor, Mahboobe,Darehkordi, Ali,Anary-Abbasinejad, Mohammad,Mohammadi, Marziyeh
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- One-pot, Three-component Synthesis of a New Series of 2-Amino-4-aroyl-5-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-carbonitrile in the Presence of SBA-15 as a Nanocatalyst
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One-pot, three-component reaction of arylglyoxals, malononitrile and 4-hydroxyquinolin-2(1H)-one in the presence of SBA-15 as a nanocatalyst and using green solvent systems under various temperatures afforded the 2-amino-4-aroyl-5-oxo-5,6-dihydro-2H-pyrano[3,2-c]quinoline-3-carbonitrile derivatives. The best yield (70-96%) were obtained using 20% mol of SBA-15 as a nanocatalyst in H2O/EtOH (1:1) at 80 °C. The simplicity of work up procedure, using green solvent system, and good to excellent yields of products are the main advantages of this synthetic strategy.
- Khalafy, Jabbar,Arlan, Fatemeh Majidi,Chalanchi, Shahin Soleimani
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p. 149 - 153
(2018/01/26)
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- A new synthesis of pyrrolo[3,2-d]pyrimidine derivatives by a one-pot, three-component reaction in the presence of L-proline as an organocatalyst
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A one-pot, three-component reaction of 4-hydroxycoumarin, arylglyoxals, and 6-aminouracil or 1,3-dimethyl-6-aminouracil in the presence of L-proline as an organocatalyst in acetic acid under reflux conditions provided a series of new pyrrolo[3,2-d]pyrimidine derivatives in good yields.
- Javahershenas, Ramin,Khalafy, Jabbar
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- A Green, Organometallic Catalyzed Synthesis of a Series of Novel Functionalized 4-Aroyl-4H-benzo[g]chromenes through One-pot, Three Component Reaction
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A new series of 4-aroyl-4H-benzo[g]chromene derivatives have been synthesized through an efficient, straightforward, and environmentally acceptable one-pot, three component reaction of malononitrile, different arylglyoxals, and 2-hydroxy-1,4-naphtoquinone (lawsone) in short reaction times and high to excellent yields. The zinc complex of amino acid L-proline, that is, Zn[L-proline]2 has been prepared and used as highly active, recyclable, noncorrosive, and water soluble Lewis acid catalyst for this transformation.
- Khalafy, Jabbar,Ilkhanizadeh, Siamand,Ranjbar, Masoumeh
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p. 951 - 956
(2018/02/15)
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- Regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates for the synthesis of indolyl diketones
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A highly regioselective N-1 and C-2 diacylation of 3-substituted indoles with arylglyoxal hydrates to afford N-1 and C-2 indolyl diketones in moderate to good yields is described. Notably, the control of regioselectivity is achieved by small changes in the Cu catalyst, additive and solvent. Importantly, the intermediates for N-1 and C-2 diacylation were detected and two plausible pathways were also proposed.
- Pan, Dalong,Chu, Jinpeng,Gao, Xianrui,Wang, Cuiping,Meng, Qingtao,Chi, Haijun,Dong, Yan,Duan, Chunying,Zhang, Zhiqiang
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supporting information
p. 6998 - 7003
(2018/10/17)
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- An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water
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An improved synthesis of 2-ethyl-5-(2-hydroxy-4-oxoquinolin-3(4H)-ylidene)-6-aryl-5,6-dihydroimidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxide derivatives 4a-k via the reaction of aryl glyoxal monohydrates 1a-k, quinoline-2,4-diol 2 and 2-amino-[1,3,4]thiadiazole (3) in the presence of Et3N/sulfamic acid in H2O is described. This green protocol is characterized by the use of the readily available catalyst and reactants, short reaction times, operational simplicity and high yields of products. The structures of all compounds were characterized by 1H NMR, 13C NMR and Fourier-transform infrared (FT-IR) spectral data and microanalyses.
- Khalafy, Jabbar,Etivand, Nasser,Khalillou, Neda
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p. 297 - 302
(2018/12/04)
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- Novel and convenient one-pot strategy for regioselective synthesis of new 5-aryl-3-methyl-1-phenyl-1,2-dihydro-7aH-pyrazolo[3,4-c]pyridazin-7a-ol derivatives
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Abstract: We describe a novel and simple regioselective synthesis of 5-aryl-3-methyl-1-phenyl-1,2-dihydro-7aH-pyrazolo[3,4-c]pyridazin-7a-ol derivatives via one-pot three-component reaction of arylglyoxalmonohydrates, 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one, and hydrazine hydrate in presence of 1,4-diazabicyclo[2.2.2]octane (DABCO) as base-organocatalyst at room temperature in acetonitrile. This one-pot method has the advantages of simple methodology, high atom economy, cost-effectiveness, high regioselectivity, and easy workup. Graphical Abstract: [Figure not available: see fulltext.].
- Rimaz, Mehdi,Mousavi, Hossein,Nikpey, Laya,Khalili, Behzad
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p. 3925 - 3937
(2017/06/20)
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- The catalyst-free syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by one-pot, three-component reactions
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Herein we report the syntheses of pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives by cyclocondensation of 1,3-diketones, 3-methyl-1-phenyl-1H-pyrazole-5-amine and arylglyoxals, under catalyst-free conditions in H2O/EtOH at reflux in 65–98% and 73–96% yields respectively. This protocol provides mild reaction conditions, good to high yields, non-catalytic, simple procedures and easy isolation of products to structurally diverse tricyclic pyrazolo[3,4-b]quinolin-5-one and pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidin-5,7-dione derivatives, which may have biological and pharmacological activities.
- Ezzati, Mahnaz,Khalafy, Jabbar,Marjani, Ahmad Poursattar,Prager, Rolf H.
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p. 6587 - 6596
(2017/10/23)
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- Catalytic asymmetric Meerwein-Ponndorf-Verley reduction of glyoxylates induced by a chiral N,N′-dioxide/Y(OTf)3 complex
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An asymmetric Meerwein-Ponndorf-Verley (MPV) reduction of glyoxylates was for the first time accomplished via an N,N′-dioxide/Y(OTf)3 complex with aluminium alkoxide and molecular sieves (MSs) as crucial additives. A variety of optically active α-hydroxyesters were obtained with excellent results. A possible reaction mechanism was proposed based on the experiments.
- Wu, Wangbin,Zou, Sijia,Lin, Lili,Ji, Jie,Zhang, Yuheng,Ma, Baiwei,Liu, Xiaohua,Feng, Xiaoming
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supporting information
p. 3232 - 3235
(2017/03/20)
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- Synthesis and antitumor evaluation of 2,3-diarylbenzofuran derivatives on HeLa cells
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2,2-Dihydroxyarylethanones, readily prepared from the commercially available aromatic ethyl ketones, were reacted with resorcinol, 3-methoxyphenol or 2-methoxyphenol in multi steps one-pot manner promoted by trifluoroacetic acid to furnish the 2,3-diarylbenzofuran derivatives in 22–95% yield. Sixteen targeted compounds were synthesized and characterized by 1H NMR, 13C NMR and HRMS. MTT assay indicated that most compounds possessed effectively inhibitory activities against the proliferation of HeLa cell. Among them, 4f had the highest inhibitory activities, with the IC50 being 13.40?±?2.04?μmol/L. Cell cycle analysis, Annexin V-FITC/propidium iodide dual staining assay and western blotting analysis revealed that 4f inhibited the proliferation of Hela cell through apoptosis induction in a dose-dependent manner via obviously up-regulated the levels of Bak and Bim, while striking down-regulated the level of Bcl-2 and Bcl-xL protein.
- He, Guo-Xue,Yuan, Jing-Mei,Zhu, Hai-Miao,Wei, Kai,Wang, Ling-Yun,Kong, Shi-Lin,Mo, Dong-Liang,Pan, Cheng-Xue,Su, Gui-Fa
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supporting information
p. 1660 - 1664
(2017/04/04)
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- Naphthol synthesis: Annulation of nitrones with alkynes: Via rhodium(III)-catalyzed C-H activation
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An efficient and redox-neutral naphthol synthesis has been realized via rhodium(iii) catalyzed C-H activation of α-carbonyl nitrones and annulation with alkynes, where the nitrone group functioned as a traceless directing group.
- Wang, Qiang,Xu, Youwei,Yang, Xifa,Li, Yunyun,Li, Xingwei
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supporting information
p. 9640 - 9643
(2017/09/01)
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- A facile and effective procedure for synthesis of polyfunctionalized pyrrolines from simultaneously stirring of carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls
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An efficient one-pot synthesis of 2H-pyrroline derivatives by a four-component reaction between carbon disulfide, aniline, arylglyoxals and β-enaminocarbonyls in acetonitrile at room temperature under mild reaction conditions is reported. The addition rea
- Masoudi, Mozhgan,Anary-Abbasinejad, Mohammad,Maleki, Alireza
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p. 2299 - 2304
(2017/10/30)
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- A Green Synthesis of 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile Derivatives by a One-pot Three-component Reaction
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The synthesis of polyfunctionalized 7-amino-5-(4-aroyl)-1,3-dimethyl-2,4-dioxo-1,2,3,4,5,8-hexahydropyrido[2,3-d]pyrimidine-6-carbonitrile derivatives by a green approach was achieved via one-pot three-component reaction of arylglyoxals, malononitrile, and 1,3-dimethyl-6-aminouracil in the presence of urea as organocatalyst in EtOH:H2O (1:1) at 60°C. This protocol provides a mild and fast procedure to structurally diverse bicyclic pyridopyrimidines in good to excellent yields.
- Javahershenas, Ramin,Khalafy, Jabbar
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p. 3163 - 3168
(2017/10/06)
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- A Green and Convenient Route for the Regioselective Synthesis of New Substituted 3-Aryl-5H-indeno[1,2-c]pyridazines as Potential Monoamine Oxidase Type A Inhibitors
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Several indeno[1,2-c]pyridazines were efficiently synthesised using the one-pot, three-component reaction of substituted indanones, arylglyoxalmonohydrates, and hydrazine in the presence of 1,5-diazabicyclo[4,3,0]non-5-ene (DBN) in water at room temperature. These substituted 3-aryl indeno[1,2-c]pyridazines can be considered as potential monoamine oxidase type A (MAOA) inhibitors. The advantages of this new strategy are the novelty of the indenopyridazine derivatives, high regioselectivity, use of water as the solvent, no requirement for toxic metal catalysts, and good to excellent yields.
- Rimaz, Mehdi,Aali, Farkhondeh,Khalili, Behzad,Prager, Rolf H.
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p. 660 - 668
(2017/05/31)
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- A direct phosphine-mediated synthesis of polyfunctionalized pyrroles from arylglyoxals and β-enaminones
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An efficient one-pot reaction for the synthesis of pyrroles from β-enaminones and arylglyoxals is reported. This reaction, which is mediated by triphenylphosphine, eliminates triphenylphosphine oxide resulting in aromatization and has been employed to access a broad range of pyrrole derivatives.
- Masoudi, Mozhgan,Anary-Abbasinejad, Mohammad
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supporting information
p. 103 - 104
(2015/12/23)
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- Regiospecific one-pot, combinatorial synthesis of new substituted pyrimido[4,5-c]pyridazines as potential monoamine oxidase inhibitors
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New 3-aryl-6-methylpyrimido[4,5-c]pyridazine-5,7(6H ,8H)-diones and 3-aryl-6-ethyl-7-thioxo-7,8-dihydropyrimido[4,5- c]pyridazin-5(6H)-ones were efficiently synthesized via a regiospecific one-pot reaction of N -methylbarbituric acid and N -ethyl-2-thiobarbituric acid with various arylglyoxal monohydrates in the presence of hydrazine dihydrochloride in ethanol at 50°C. The target compounds were obtained in high yields and were regioisomerically pure after recrystallization. These new heterocycles may act as potential MAOB inhibitors.
- Rimaz, Mehdi,Pourhossein, Paria,Khalili, Behzad
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p. 244 - 254
(2015/05/27)
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- Two efficient one-pot approaches for regioselective synthesis of new 3-arylpyridazino[4,3-c]quinolin-5(6H)-ones
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Two efficient regioselective approaches for the one-pot synthesis of 3-arylpyridazino[4,3-c]quinolin-5(6H)-one derivatives are reported, by the three-component reaction of arylglyoxal monohydrates, quinoline-2,4-diol, and hydrazinium dihydrochloride or hydrazine hydrate in ethanol and pyridine. In ethanol, the reactions were catalyzed by 1,4-diazobicyclo[2,2,2]octane. The features of both procedures are high regioselectivity, mild reaction conditions, good to high yields, and operational simplicity.
- Rimaz, Mehdi
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p. 1529 - 1534
(2015/10/20)
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- Molybdate sulfuric acid-catalyzed one-pot synthesis of substituted coumarins under solvent-free conditions
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An efficient method for the synthesis of new aryloylamido coumarins via a one-pot, three-component reaction of an aryl glyoxal, benzamide, and a 4-hydroxycoumarin in the presence of molybdate sulfuric acid under solvent-free conditions is reported. This h
- Khodabakhshi, Saeed,Karami, Bahador,Eskandari, Khalil
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p. 7263 - 7272
(2015/09/29)
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- Synthesis of the major isomers of Aprepitant and Fosaprepitant
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The synthesis of two isomers of Aprepitant (APT) and three isomers of Fosaprepitant (FPT), crucial components for quality control in manufacturing, is described. Herein, three chiral centers in the isomers of Aprepitant are established in high yield by in
- Wan, Wei-Li,He, Yun,Guan, Mei,Li, Xiao-Long,Cheng, Xu,Wu, Yong
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p. 1118 - 1122
(2014/01/06)
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- Regiospecific synthesis of novel furo[4,5- c ]coumarins in a one-pot reaction
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A new and expedient assembly of an interesting class of amido-substituted furo[4,5-c]coumarins has been successfully achieved through a one-pot sequential coupling and cyclization strategy starting from 4-hydroxycoumarin, aryl glyoxals and benz-amide. All
- Karami, Bahador,Khodabakhshi, Saeed,Eskandari, Khalil
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p. 998 - 1000
(2013/06/27)
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- A highly efficient and enantioselective intramolecular cannizzaro reaction under TOX/Cu(II) catalysis
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An asymmetric intramolecular Cannizzaro reaction of aryl and alkyl glyoxals with alcohols has been realized with an unprecedented high level of enantioselectivity, on the basis of a newly developed congested TOX ligand and a gradual liberation protocol of active glyoxals from glyoxal monohydrates. Preliminary results suggested a mechanism of enantioselective addition of alcohols to glyoxals contributing most to the stereoselectivity, other than by the dynamic kinetic resolution of hemiacetal intermediates.
- Wang, Pan,Tao, Wen-Jie,Sun, Xiu-Li,Liao, Saihu,Tang, Yong
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supporting information
p. 16849 - 16852
(2013/12/04)
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- Microwave-assisted selenium dioxide oxidation of aryl methyl ketones to aryl glyoxals
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We report an improved procedure for the synthesis of phenyl glyoxal and a series of para-substituted aryl glyoxals by microwave-assisted selenium dioxide oxidation. The reaction time has been reduced from several hours to three minutes for activated aryl methyl ketone substrates and 18 min for deactivated substrates, with all reactions affording quantitative conversion into the corresponding aryl glyoxals.
- Young, Ryan M.,Davies-Coleman, Michael T.
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experimental part
p. 4036 - 4038
(2011/08/09)
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- Catalytic oxidations of enolizable ketones using 2-alkylidene-4- oxothiazolidine vinyl bromide
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Direct oxidation of enolizable ketones to α-hydroxy derivatives, vicinal dicarbonyls or tricarbonyl compounds has been achieved by a catalytic amount of 2-alkylidene-4-oxothiazolidine vinyl bromide in DMSO as a solvent. The yields range from moderate to good.
- Baranac-Stojanovi?, Marija,Markovi?, Rade,Stojanovi?, Milovan
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experimental part
p. 8000 - 8008
(2011/11/06)
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- Practical asymmetric synthesis of aprepitant, a potent human NK-1 receptor antagonist, via a stereoselective Lewis acid-catalyzed trans acetalization reaction
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A streamlined and high-yielding synthesis of aprepitant (1), a potent substance P (SP) receptor antagonist, is described. The enantiopure oxazinone 16 starting material was synthesized via a novel crystallization-induced dynamic resolution process. Conversion of 16 to the penultimate intermediate cis-sec-amine 9 features a highly stereoselective Lewis acid-catalyzed trans acetalization of chiral alcohol 3 with trichloroacetimidate 18 followed by inversion of the adjacent chiral center on the morpholine ring. The six-step process for the synthesis of 9 was accomplished in extremely high overall yield (81%) and with only two isolations.
- Zhao, Matthew M.,McNamara, James M.,Ho, Guo-Jie,Emerson, Khateeta M.,Song, Zhiguo J.,Tschaen, David M.,Brands, Karel M. J.,Dolling, Ulf-H,Grabowski, Edward J. J.,Reider, Paul J.,Cottrell, Ian F.,Ashwood, Michael S.,Bishop, Brian C.
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p. 6743 - 6747
(2007/10/03)
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- Fluorine Containing Bioactive Heterocycles. Part II. Synthesis of Some New Fluorine Containing Arylglyoxals, Their Hydrates and 1,5-Disubstituted Hydantoins
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Eight new fluorine containing arylglyoxals have been synthesized by the oxidation of the active methyl group of fluorinated acetophenones by selenium dioxide in dioxan-water medium.The corresponding hydrates were obtained by dissolving arylglyoxals in minimum amounts of benzene and adding hot water.Seventeen new fluorine containing 1,5-disubstituted hydantoins were subsequently prepared by the condensation of these glyoxals with arylureas in ethanol and characterized by ir, pmr and mass spectral studies.Representative compounds have been screened for their possible anticonvulsant and analgesic activities.None of the compounds show significant analgesic activity.
- Joshi, Krishna C.,Pathak, Vijai N.,Goyal, Mahendra K.
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p. 1651 - 1653
(2007/10/02)
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