- Combined KOH/BEt3Catalyst for Selective Deaminative Hydroboration of Aromatic Carboxamides for Construction of Luminophores
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The selective catalytic C-N bond cleavage of amides into value-added amine products is a desirable but challenging transformation. Molecules containing iminodibenzyl motifs are prevalent in pharmaceutical molecules and functional materials. Here we established a combined KOH/BEt3 catalyst for deaminative hydroboration of acyl-iminodibenzyl derivatives, including nonheterocyclic carboxamides, to the corresponding amines. This novel transition-metal-free methodology was also applied to the construction of Clomipramine and luminophores.
- Li, Jinshan,Wang, Jiali,Yang, Jianguo,Yao, Wubing,Zhong, Aiguo
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supporting information
p. 8086 - 8090
(2020/11/03)
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- Intermediate compound, carbamazepine and derivative thereof as well as preparation method of oxcarbazepine and derivative thereof
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The invention provides an intermediate compound, carbamazepine and a derivative thereof as well as a preparation method of oxcarbazepine and a derivative thereof. 2-substituted aminophenylacetate or 2-substituted aminophenylacetonitrile and 2-halobenzonitrile are used as raw materials, substitution reaction, intramolecular condensation reaction, hydrolysis and hydrochloric acid acidification are carried out to obtain the oxcarbazepine and the derivative 5-substituent-10-oxa-10, 11-dihydro-5H-dibenzo [b, f] aza thereof, and the derivative of the oxcarbazepine can be used as a raw material to prepare the carbamazepine and the derivative 5-substituted iminostilbene thereof, an intermediate compound iminostilbene and intermediate compounds 5-substituted-10-methoxyiminostilbene and 10-methoxyiminostilbene. The raw materials used in the method are cheap and easy to obtain, and the cost is low; the preparation method is simple, conditions are easy to realize, the method is simple, convenientand safe to operate, and the process flow is short; the production amount of three wastes is small, and thus, the method is environmentally friendly; and a target product has high yield and purity, and is suitable for industrial production.
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- Hydride-catalyzed selectively reductive cleavage of unactivated tertiary amides using hydrosilane
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The first hydride-catalyzed reductive cleavage of various unactivated tertiary amides, including the biologically active aryl-phenazine carboxamides and the challenging non-heterocyclic carbonyl functions, using low-cost hydrosilane as a reducing reagent has been developed. The novel catalyst system exhibits high efficiency and exclusive selectivity, providing the desired amines in useful to excellent yields under mild conditions. Overall, this transition metal-free process may offer a versatile alternative to currently employed expensive reducing reagents, high-pressure hydrogen or metal systems for the selective reductive cleavage of amides.
- Yao, Wubing,Li, Rongrong,Yang, Jianguo,Hao, Feiyue
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p. 3874 - 3878
(2019/08/07)
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- A disubstituted amide derivatives decarbonylation hydrogenation green new method (by machine translation)
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The invention relates to a high efficiency, high selectivity of the disubstituted amide derivatives of decarbonylation hydrogenation reaction green new method. For the first time to the metallic compound triethylborane as catalyst, under mild conditions can be conveniently catalytic N, N - di-aryl substituted amide and its derivative and cheap and easy to obtain organic silicon reagent selective preparation of secondary organic amine product. Compared with the traditional method, the new method generally has the wide substrate universality, functional group compatibility outstanding, simple operation and the like. For the first time in order to realize the organic silicon reagent as reducing agent and amide compounds decarbonylation hydrogenation reaction, is the reduction of amides and derivatives thereof, in particular the organic light-emitting diodes (OLEDs) material unit - diaryl amine compound of the laboratory preparation or industrial production provides a brand-new "green" response strategies. (by machine translation)
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Paragraph 0042; 0043; 0044; 0045
(2018/02/04)
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- A new industrial process for 10-methoxyiminostilbene: Key intermediate for the synthesis of oxcarbazepine
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A new industrial process, involving only two isolation and drying steps, for 10-methoxyiminostilbene (MISB), an advance intermediate of widely prescribed antiepileptic drug, oxcarbazepine, has been developed. A salient feature of this process is the novel use of 1,3-dibromo-5,5-dimethylhydantoin (DBDMH) to afford bro-mohydrin methyl ether from N-acetyliminostilbene. The byproducts of this process namely acetic acid, 5,5-dimethylhydantoin and Et3N HBr are recyclable as well as nontoxic This process is amenable for the large-scale production of MISB.
- Singh, Harnam,Gupta, Nitin,Kumar, Pramod,Dubey, Sushil K.,Sharma, Pawan K.
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experimental part
p. 870 - 874
(2010/04/22)
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- Process for the Preparation of 10,11-Dihydro-10-Oxo-5H-Dibenz[B,F] Azepine-5-Carboxamide
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A process for preparing 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxamide, compound of formula (I), said process comprising a. reacting compound of formula (Ivb) with alkali metal methoxide to yield compound of formula (II); and b. converting compound of formula (II) to compound of formula (I).
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Page/Page column 4
(2008/12/04)
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- PROCESS FOR PRODUCING OXCARBAZEPINE VIA AN 11-ALKOXY-10-HALO-DIHYDROIMINOSTILBENE INTERMEDIATE
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Disclosed herein is an economically viable and cost effective process for preparation of oxcarbazepine of formula (I) via a novel intermediate of formula (XVIII).
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Page/Page column 14
(2010/11/29)
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- A new industrial process for oxcarbazepine
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A novel industrial process for the antiepileptic drug oxcarbazepine 1 has been developed. Unlike the old process, the new process is free from halogenated solvents and can be performed in standard production equipment. It starts from commercially available 1,3-dihydro-1-phenyl-2H-indol-2-one 10. In the key step, an electrophilic ring closure reaction of 2-[(methoxycarbonyl)phenylamino] benzeneacetic acid 5 to 10,11-dihydro-10-oxo-5H-dibenz[b,f]azepine-5-carboxylic acid methyl ester 6 in poly phosphoric acid was applied. For the manufacture of 5, a highly efficient process using a dianion strategy was developed.
- Fuenfschilling, Peter C.,Zaugg, Werner,Beutler, Ulrich,Kaufmann, Daniel,Lohse, Olivier,Mutz, Jean-Paul,Onken, Ulrich,Reber, Jean-Louis,Shenton, David
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p. 272 - 277
(2012/12/24)
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- A new synthesis of oxcarbazepine using a Friedel-Crafts cyclization strategy
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A novel, simple, and straightforward process for the large-scale synthesis of oxcarbazepine, the active ingredient of Trileptal, a medicine for the treatment of epilepsy, has been developed. Starting from readily available 1,3-dihydro-1-phenyl-2H-indol-2-one, a Friedel-Crafts cyclization strategy provides a direct route to the tricyclic framework of the target molecule. Crucial to the success of the strategy was the choice of the proper nitrogen-protecting group.
- Kaufmann, Daniel,Fünfschilling, Peter C.,Beutler, Ulrich,Hoehn, Pascale,Lohse, Olivier,Zaugg, Werner
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p. 5275 - 5278
(2007/10/03)
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- Dibenzo(b,f)azepine derivatives and their preparation
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The invention relates to new processes for the preparation of the pharmaceutical oxcarbazepine, as well as novel intermediates prepared by or used for said processes, and the preparation of said intermediates.
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- New synthesis of oxcarbazepine via remote metalation of protected N-o-tolyl-anthranilamide derivatives
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Benzyl and allyl protected N-o-tolyl-anthranilamides were efficiently prepared by Buchwald-Hartwig C-N cross coupling reactions, followed by protection of the amino group. Under directed remote metalation conditions, protected dibenzoazepinones were obtained in good yields. Deprotection of the amine and conversion to an urea furnished a new and efficient synthesis of the antiepileptic drug Trileptal.
- Lohse, Olivier,Beutler, Ulrich,Fünfschilling, Peter,Furet, Pascal,France, Julien,Kaufmann, Daniel,Penn, Gerhard,Zaugg, Werner
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p. 385 - 389
(2007/10/03)
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- New synthesis of 10-alkoxy-5-H-dibenz[b,f]azepines
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The reaction of 5-acetyl-5H-dibenz[b,f]azepines with sodium-hypochlorite led to the 5-acetyl-10,11-epoxy-10,11-dihydro-5H-dibenz[b,f]azepine (1). The lithium iodide induced rearrangement of 1 gave the keton 2 which was reacted with trialkyl-orthoformates leading to the vinyl ethers 3a,b.
- Haasz,Galamb
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p. 683 - 687
(2007/10/02)
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- Imipramine derivatives and poly(amino acid) conjugates
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Imipramine functionalized compounds are provided for conjugation to antigenic compounds, particularly poly(amino acids), and enzymes. The antigenic conjugates are employed for the production of antibodies, which find particular use in immunoassays for the determination of imipramine, while the enzyme conjugate finds use in a homogeneous enzyme assay for the determination of imipramine.
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