- A highly efficient copper-catalyzed method for the synthesis of 2-hydroxybenzamides in water
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An efficient copper-catalyzed synthetic method for the preparation of 2-hydroxybenzamides is described for the first time from 2-chlorobenzamide substrates using copper iodide/1,10-phenanthroline and a base, potassium hydroxide, in neat water. By using this reaction, a series of 2-hydroxybenzamides with functional groups such as fluoro, chloro, iodo, methoxy, amide, and alcohol have been obtained in 33-96% yield. Other aromatic 2-chloroarylamides such as naphthalene, pyridine, and thiophene are found to be equally compatible to the reaction. It is proposed that the reaction proceed via formation of copper-amide complex, which may facilitate the hydroxylation in water. Overall, the first report on copper-catalyzed hydroxylation reaction in water and first catalytic route for the synthesis of 2-hydroxybenzamides is presented. Simple purification procedure and convenience of employing low-cost reagents in neat water make this method practical and economical for the synthesis of 2-hydroxybenzamides. Georg Thieme Verlag Stuttgart · New York.
- Balkrishna, Shah Jaimin,Kumar, Sangit
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experimental part
p. 1417 - 1426
(2012/06/30)
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- Cu-catalyzed efficient synthetic methodology for ebselen and related se-N heterocycles
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An efficient copper-catalyzed method for the synthesis of biologically important ebselen and related analogues containing a Se-N bond has been developed. This is the first report of a catalytic process of selenation and Se-N bond formation reaction. Copper-catalyzed reaction tolerates functional groups such as amides, hydroxyls, ethers, nitro, fluorides, and chlorides. The best results are obtained by using a combination of potassium carbonate as a base, iodo- or bromo-arylamide substrates, selenium powder, and copper iodide catalyst.
- Balkrishna, Shah Jaimin,Bhakuni, Bhagat Singh,Chopra, Deepak,Kumar, Sangit
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supporting information; body text
p. 5394 - 5397
(2011/02/26)
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- PYRAZOLE COMPOUNDS AND USE THEREOF
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The pyrazole compound of the present invention is represented by the following general formula (I). The pyrazole compound of the present invention or a salt thereof or a solvate thereof potently inhibits liver glycogen phosphorylase, and, therefore, is useful as a therapeutic or prophylactic agent for diabetes. wherein each symbol denotes as described in the specifications.
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Page/Page column 21
(2009/05/29)
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- NOVEL COMPOUNDS
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The invention relates to substituted phenylacetic acids as useful pharmaceutical compounds for treating respiratory disorders, pharmaceutical compositions containing them, and processes for their preparation.
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Page/Page column 76
(2008/06/13)
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- PYRAZOLE COMPOUND AND THERAPEUTIC AGENT FOR DIABETES COMPRISING THE SAME
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A pyrazole compound represented by the general formula (I) or a salt thereof which has a hepatic glycogen phosphorylase inhibitory activity and therefore is useful as a therapeutic or prophylactic agent for diabetes or a pharmacologically salt thereof : wherein the ring Q represents an aryl group or an aromatic heterocyclic group; R1 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group or a C1-6 alkoxy group; R2 represents a halogen atom, a C1-6 alkyl group, a C1-6 alkoxy group or an azide group; R3 represents a halogen atom, a hydroxyl group, a C1-6 alkyl group, a halo-C1-6 alkyl group, a C1-6 alkoxy group, an azide group, an amino group, an acylamino group or a C1-6 alkylsulfonylamino group; R4 and R5 independently represent a hydrogen atom, a C1-6 alkyl group which may be substituted, a a C3-8 cycloalkyl group, a saturated heterocyclic group which may be substituted, an aryl group which may be substituted, a C7-14 aralkyl group, an aromatic heterocyclic group or the like.
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Page/Page column 245-246
(2008/06/13)
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- PROCESSES FOR THE PREPARATION OF PYRAZOLO[1,5-a]-1,3,5-TRIAZINES AND INTERMEDIATES THEREOF
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The present invention provides novel processes and intermediates for preparing corticotropin releasing factor (CRF) receptor antagonists having the structure below which are useful in treating CRF-related disorders such as anxiety and depression.
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Page/Page column 34
(2010/02/11)
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- Method of preparing fluoroaromatic compounds
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The present invention provides a method of preparing ortho-difluorobenzene derivatives, which comprises (a) providing a mixture of cyclohexenes by reacting chlorotrifluoroethylene (CTFE) and 1,3-diene in a flow reactor and distilling the resultant, and (b) dehydrohalogenating the mixture of cyclohexenes with a phase transition catalyst in the presence of alkali metal hydroxide at temperature range of 40 to 150 °C without using any organic solvent. The distillate having low boiling point, which is obtained during distillation of the resultant, is recycled into the flow reactor. The present invention also provides a method of preparing 2-chloro-4,5-difluorobenzoic acid, which comprises (a) providing a mixture of 4-chloro-1-methyl-4,5,5-trifluorocyclohexene and 5-chloro-1-methyl-4,4,5-trifluorocyclohexene by reacting chlorotrifluoroethylene (CTFE) and isoprene and distilling the resultant, (b) dehydrohalogenating said mixture in the presence of alkali metal hydroxide and a phase transition catalyst to form 3,4-difluorotoluene, (c) reacting said 3,4-difluorotoluene with chlorine gas without using any organic solvent to form 2-chloro-4,5-difluorotoluene, (d) photo-reacting said 2-chloro-4,5-difluorotoluene with chlorine gas under a lighting mercury lamp without using any organic solvent to form 2-chloro-4,5-difluorobenzotrichloride, and (e) reacting said 2-chloro-4,5-difluorobenzotrichloride with aqueous acid solution without using any organic solvent. The present invention also provides a method of preparing 2-chloro-4,5-difluorobenzoyl chloride by reacting the 2-chloro-4,5-difluorobenzotrichloride of step (e) above with zinc oxide.
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- Method of preparing fluoroaromatic compounds
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The present invention provides a method of preparing ortho-difluorobenzene derivatives, which comprises (a) providing a mixture of cyclohexenes by reacting chlorotrifluoroethylene (CTFE) and 1.3-diene in a flow reactor and distilling the resultant, and (b) dehydrohalogenating the mixture of cyclohexenes with a phase transition catalyst in :he presence of alkali metal hydroxide at temperature range of 40 to 150° C. without using any organic solvent. The distillate having low boiling point, which is obtained during distillation of the resultant, is recycled into the flow reactor. The present invention also provides a method of preparing 2-chloro-4,5-difluorobenzoic acid, which comprises (a) providing a mixture of 4-chloro-1-methyl-4,5,5-trifluorocyclohexene and 5-chloro-1-methyl-4,4,5-trifluorocyclohexene by reacting chlorotrifluoroethylene (CTFE) and isoprene and distilling the resultant. (b) dehydrohalogenating said mixture in the presence of alkali metal hydroxide and a phase transition catalyst to form 3,4-difluorotoluene, to reacting said 3,4-difluorotoluene with chlorine gas without using any organic solvent to form 2-chloro-4,5-difluorotoluene, (d) photo-reacting said 2-chloro-4,5-difluorotoluene with chlorine gas under a lighting mercury lamp without using any organic solvent to form 2-chloro-4,5-difluorobenzotrichloride, and (e) reacting said 2-chloro-4,5-difluorobenzotrichloride with aqueous acid solution without using any organic solvent. The present invention also provides a method of preparing 2-chloro-4,5-difluorobenzoyl chloride by reacting the 2-chloro-4,5-difluorobenzotrichloride of step (e) above with zinc oxide.
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- PREPARATION OF 1-HYDROXYXANTHEN-9(9H)-ONES AND 1-HYDROXYACRIDIN-9(10H)-ONES VIA CORRESPONDING 3,4-DIHYDRO-1,9(2H)-DIONES
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Target 10-cyclopropyl-7-fluoro-6-(4-methyl-1-piperazinyl)acridin-9(10H)-one (IVc) and 7-fluoro-1-hydroxy-6-(4-methyl-1-piperazinyl)-9H-xanthen-9-one (IVd) were obtained from corresponding difluoro derivatives IVa and IVb, respectively.These intermediates were synthesized via respective 3,4-dihydro-1,9(2H)-diones Va and Vb.Acridine derivative (10-cyclopropyl-6,7-difluoro-3,4-dihydro-1H-acridine-1,9(2H,10H)-dione, Va) was synthesized from 1-cyclopropyl-6,7-difluoroisatoic anhydride (XI) and xanthene derivative (6,7-difluoro-3,4-dihydro-1H-xanthen-1,9(2H)-dione, Vb) from cyclohexenone derivative VIb.Several unsuccessful attempts to prepare hydroxyacridone IVc and/or some useful intermediates of its synthesis are also described.
- Radl, Stanislav
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p. 2127 - 2136
(2007/10/03)
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- Fluorinated benzoyl compounds
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A 2-chloro-4,5-difluorobenzoyl compound of the formula: STR1 wherein R2 is a lower alkyl group, and R7 is a 2,4-difluorophenyl group or a 4-fluorophenyl group.
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- Process for preparing fluorinated benzoyl compounds
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Fluorinated benzoyl compounds of the formula: STR1 wherein Q is a lower alkyl group, a halogen atom, --CH2 CO2 R1 wherein R1 is a lower alkyl group, or STR2 wherein each of R2 and R3 is a lower alkyl group, are disclosed.
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- Intermediates for preparing 1,4-dihydro-4-oxo-quinoline-3-carboxylic acid esters
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Compounds of the formula: wherein Y is OR1, fluoro, chloro, methyl, R1, and R3 are independently selected from hydrogen and C1-C4 alkyl, R2 is C1-C4 alkyl and X is fluoro, chloro or bromo, with the proviso that when Y is OH, X cannot be bromo and with the proviso that X can be fluoro only if R2 is methyl.
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