- Rhodium-Catalyzed Asymmetric Hydrogenation of 3-Benzoylaminocoumarins for the Synthesis of Chiral 3-Amino Dihydrocoumarins
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An asymmetric hydrogenation of 3-benzoylaminocoumarins was achieved for the first time using our BridgePhos-Rh catalytic system, providing chiral 3-amino dihydrocoumarins in high yields (up to 98 %) and with excellent enantioselectivities (up to 99.7 % ee). The relationship between the enantioselectivities of the hydrogenations and the dihedral angles and the resulting π-π stacking effects of the BridgePhos-Rh complexes, which were determined by X-ray diffraction analysis, are discussed. The corresponding hydrogenated products allow for many transformations, providing several chiral skeletons with important physiological and pharmacological activities.
- Xu, Yunnan,Liu, Delong,Deng, Yu,Zhou, Yi,Zhang, Wanbin
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supporting information
p. 23602 - 23607
(2021/10/05)
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- Evaluation of trypanocidal and antioxidant activities of a selected series of 3-amidocoumarins
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Background: Neglected diseases are becoming more prevalent due to globalization. This has inspired active research in the development of new drugs for the treatment of parasitic diseases such as Chagas disease. Objectives: With the aim of finding new tryp
- Moncada-Basualto, Mauricio,Lapier, Michel,Maya, Juan Diego,Matsuhiro, Betty,Olea-Azar, Claudio,Delogu, Giovanna L.,Uriarte, Eugenio,Santana, Lourdes,Matos, Maria Jo?o
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p. 573 - 584
(2018/08/17)
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- Development of novel adenosine receptor ligands based on the 3-amidocoumarin scaffold
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With the aim of finding new adenosine receptor (AR) ligands presenting the 3-amidocoumarin scaffold, a study focusing on the discovery of new chemical entities was carried out. The synthesized compounds 1-8 were evaluated in radioligand binding (A1/
- Matos, Maria J.,Vilar, Santiago,Kachler, Sonja,Celeiro, Maria,Vazquez-Rodriguez, Saleta,Santana, Lourdes,Uriarte, Eugenio,Hripcsak, George,Borges, Fernanda,Klotz, Karl-Norbert
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- 3-Amidocoumarins as Potential Multifunctional Agents against Neurodegenerative Diseases
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Monoamine oxidase (MAO) generates reactive oxygen species (ROS), which cause neuronal cell death, causing neurodegeneration. Agents that are able to concurrently inhibit MAO and scavenge free radicals represent promising multifunctional neuroprotective ag
- Matos, Maria Jo?o,Rodríguez-Enríquez, Fernanda,Borges, Fernanda,Santana, Lourdes,Uriarte, Eugenio,Estrada, Martín,Rodríguez-Franco, María Isabel,Laguna, Reyes,Vi?a, Dolores
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p. 2071 - 2079
(2015/12/23)
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- A one-pot [Bmim]OH-mediated synthesis of 3-benzamidocoumarins
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The first example of an ionic liquid-promoted one-pot synthesis of 3-benzamidocoumarins from salicylaldehydes and 2-pheny-1,3-oxazolan-5-one via Knoevenagel condensation-ring transformation cascades has been reported. No by-product formation, operational
- Yadav, Lal Dhar S.,Singh, Santosh,Rai, Vijai K.
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experimental part
p. 2208 - 2212
(2009/08/07)
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- Synthesis and antihyperglycemic activity of novel N-acyl-2-arylethylamines and N-acyl-3-coumarylamines
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A series of novel N-acyl-2-arylethylamines and N-acyl-3-coumarylamines were synthesized and evaluated for their antihyperglycemic activity. Compounds 3g and 6d exhibited lowering of postprandial plasma glucose by 30.7%, 23.3% in SLM and 25.6%, 25.4% in STZ models respectively which is significant compared to metformin and glybenclamide. Other compounds exhibited moderate to good activity ranging from 19.5% to 32.8% in SLM and 3.26% to 25.4% in STZ models.
- Dwivedi, Atma P.,Kumar, Shailesh,Varshney, Vandana,Singh, Amar B.,Srivastava, Arvind K.,Sahu, Devi P.
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p. 2301 - 2305
(2008/09/21)
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- An efficient and facile synthesis of substituted 3-aminocoumarins under mw irradiation in dry media
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A variety of 3-aminocoumarins were prepared by reaction of salicylaldehyde derivatives with benzoylglycine catalyzed by piperidine under microwave irradiation (MWI) and subsequent acid hydrolysis. The structure of products was proven by elemental analysis, IR, NMR and Mass spectra. These investigations will contribute to development of environmentally friendly and inexpensive processes in organic synthesis.
- Valizadeh, Hassan,Shockravi, Abbas
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p. 475 - 478
(2007/10/03)
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- Synthesis of 2-methyl-9-oxo-9H-furo[2,3-c]benzo pyrans and 2-methyl- 3H,4H[1]benzopyrano[3,4-b]pyrrol-4-ones
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3:4-Fused furocoumarins and pyrrolocoumarins are synthesised from 3- hydroxy and 3-benzamido- substituted coumarins by a novel two step sequence.
- Raghu Ram,Krupadanam,Srimannarayana
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p. 2421 - 2428
(2007/10/03)
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- A facile synthesis of 2(H)-oxo-3-substituted-1-benzopyrans
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A simple and efficient synthesis of 2(H)-oxo-1-benzopyrans 3 in asingle step from salicylaldehyde and malonate derivatives catalysed by anhydrous zinc chloride has been described.
- Srinivas, K.,Krishna, K. L.,Sivaprasad, A.,Rao, P. Shanthan
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p. 936 - 938
(2007/10/03)
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- Reaction of unsaturated azlactones with sulfur nucleophiles: some observations
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Unsaturated azlactones undergo thiolysis with toluene-α-thiol, but 2-substituted (Z)-4-o-acetoxybenzylidene-4,5-dihydrooxazol-5-ones form 3-acylaminocoumarins in the presence of triethylamine.Sodium sulfide in ethanol brings about ethanolysis of the 1,5 b
- Mukerjee, Arya K.,Rao, Laxmi,Homami, Seyed Saied,Joseph, Kiran
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p. 1383 - 1387
(2007/10/02)
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- 4-(2'-Hydroxyphenylmethylene)-2-phenyloxyzol-5(4H)-one: A Comedy of Errors
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Eighteen publications since 1955 have described properties and reactions of the title compound.All these reports are erroneous and refer, variously, to three other substances.All literature reports of the analogous 4-(2'-hydroxyphenylmethylene)-2-methyloxazol-5(4H)-one also need revision.A convenient synthesis of the title compound 3 (R=H), its chemical and physical properties, and its rearrangement to 3-benzoylamino-1-benzopyran-2-one 1, are reported here for the first time.A mechanism is presented for the observed course of Ploechl-Erlenmeyer syntheses with salicylaldehyde and with 2-acetoxybenzaldehyde.
- Cornforth, Sir John,Ming-hui, Du
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p. 2183 - 2187
(2007/10/02)
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- Thiol-induced Conversion of (Z)-4-o-Acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-ones into 3-Benzoylaminocoumarins
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Toluene-α-thiol induces cleavage of the 1,5-bond of (Z)-4-o-acetoxybenzylidene-2-phenyl-4,5-dihydrooxazol-5-ones in triethylamine-containing ethanol to give 3-benzoylaminocoumarins.
- Mukerjee, Arya K.,Joseph, Kiran,Rao, Laxmi
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p. 2611 - 2612
(2007/10/02)
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- A Facile Synthesis of 3-Acylaminocoumarins
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2-Methyl/phenyl-2-oxazolin-5-ones (2a,b), generated by cyclising aceturic and hippuric acids respectively with benzenesulphonyl chloride and triethylamine in benzene, undergo condensation with salicylaldehyde to give 3-acetyl/benzoylaminocoumarins (4a,b) which afford 3-aminocoumarin (5) on acid hydrolysis.Hydrolysis of 4b with KOH gives 3-hydroxycoumarin (6) and/or 2-benzoylamino-o-hydroxycinnamic acid (9).
- Tripathy, Pradeep K.,Mukerjee, Arya K.
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- Phenyl Isothiocyanate - Mediated Cyclocondensation of Hippuric Acid in the Presence of Salicylaldehyde / o-Hydroxyacetophenone
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Hippuric acid (1), when heated with phenyl isothiocyanate (2) and salicylaldehyde (3a) at 170 deg for 30 min, affords 3-N-benzoylaminocoumarin (4a) and (Z)-4-(o-hydroxybenzylidene)-1,2-diphenyl-2-imidazolin-5-one (5). o-Hydroxyacetophenone affords hippuranilide as the main product, though 4b is discernible by TLC.
- Ashare, Ram,Mukerjee, Arya K.
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p. 423 - 424
(2007/10/02)
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- Reactions of 2-Phenyl-2-oxazolin-5-ones with Imines and Their Corresponding Carbonyl Compounds
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The addition of 2-phenyl-2-oxazolin-5-ones (3) to benzylideneaniline, salicylideneaniline, benzaldehyde or salicylaldehyde affords different products depending upon the nature of the reactants.
- Kumar, Pradeep,Mukerjee, Arya K.
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p. 418 - 420
(2007/10/02)
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- Reactions of 2-Substituted 5-Oxazolones with Imines Carrying a Vicinal Hydroxyl Group & Salicylaldehyde
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5-Oxazolones, generated by cyclising N-acylglycines with ethyl chloroformate, react with imines carrying a vicinal hydroxyl group and also with salicylaldehyde.Unsaturated 5-oxazolone or 3-N-acylaminocoumarin is obtained depending on the type of reactants.
- Kumar, Pradeep,Mukerjee, Arya K.
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p. 704 - 707
(2007/10/02)
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