4904-83-0

Usage

Uses

Used in Pharmaceutical Industry:
5,11-dihydro-5-methyl-10H-dibenz[b,f]azepin-10-one is used as a key intermediate in the synthesis of Metapramine (M225830), a norepinephrine reuptake inhibitor. It is specifically designed to inhibit the reuptake of norepinephrine without affecting the reuptake of serotonin or dopamine, making it a valuable compound for the development of medications to treat conditions related to the imbalance of these neurotransmitters, such as attention deficit hyperactivity disorder (ADHD) and certain mood disorders.

InChI:InChI=1/C15H13NO/c1-16-13-8-4-2-6-11(13)10-15(17)12-7-3-5-9-14(12)16/h2-9H,10H2,1H3

Upstream product

• 207802-82-2 N,N-diethyl-2-(2,N-dimethylanilino)benzamide 
• 5003-62-3 10-methoxy-5-methyl-5H-dibenzo[b,f]azepine 
• 1093239-41-8 N,N-dimethyl-2-(2,N-dimethylanilino)benzamide 
• 1093239-43-0 N,N-diisopropyl-2-(2,N-dimethylanilino)benzamide 
• 50777-64-5 2-(2-bromophenyl)-2-methyl-1,3-dioxolane 
• 1352449-00-3 2-chloro-N-(2-(2-methyl-1,3-dioxolan-2-yl)phenyl)aniline 
• 1352449-01-4 N-methyl-N-(2-chlorophenyl)-2'-aminoacetophenone 
• 95-51-2 o-chloroaniline 
• 4217-54-3 9,10-dihydro-10-methylacridine 
• 719-54-0 10-methyl-9, 10-dihydro-9-acridinone 
• 52249-32-8 N-methyldibenzazepine 
• 578-95-0 10H-acridin-9-one 
• 28291-62-5 5-methyl-10,11-dihydro-5H-dibenzo[b,f]azepin-10-ol 
• 88975-25-1 2-(2-(methylamino)phenyl)acetonitrile 

Downstream Products

• 52249-32-8 N-methyldibenzazepine 
• 84142-01-8 chloro-8 methyl-5 5H-dibenzylazepine-10-ethanamine 
• 28941-77-7 Dimethyl-(5-methyl-5H-dibenzo[b,f]azepin-10-ylmethyl)-amine; hydrochloride 
• 84142-00-7 methyl-4 benzene sulfonate de chloro-8 methyl-5 5H-dibenzazepine-10-ethanol 
• 52813-87-3 ethylthio-8 methyl-5 5H-dibenzazepine-10-acetate de nitro-4 phenyle 
• 52813-96-4 [2-(8-Ethanesulfonyl-5-methyl-5H-dibenzo[b,f]azepin-10-yl)-ethyl]-methyl-amine 

Relevant academic research and scientific papers

Intermediate compound, carbamazepine and derivative thereof as well as preparation method of oxcarbazepine and derivative thereof

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.

Oxidative C-H bond functionalization and ring expansion with TMSCHN2: A copper(I)-catalyzed approach to dibenzoxepines and dibenzoazepines

Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for the pharmaceutical industry and academic research. However, their syntheses are generally rather tedious, requiring several steps that involve a Wagner-Meerwein-type rearrangement under harsh conditions. Herein, we present the first copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion with TMSCHN2 to yield these important derivatives in a facile and straightforward way. Cut a long story short: Tricyclic dibenzoxepines and dibenzazepines are important therapeutic agents for pharmaceuticals, but their syntheses are generally rather tedious. A copper(I)-catalyzed oxidative C-H bond functionalization and ring expansion sequence with TMSCHN2 has been developed to yield these important derivatives in a facile and straightforward way.

Synthesis of benzo-fused heterocycles by intramolecular α-arylation of ketone enolate anions

A two-step synthesis of six-, seven-, eight-, and nine-member benzo-fused heterocycles in good to excellent yields is reported. The synthetic strategy involves the generation of a new intramolecular α-aryl ketone bond by the photostimulated SRN1 reaction of ketone enolate anions linked to a pendant haloarene as the key step. On the other hand, an intramolecular C Ar-CAr coupling led to the formation of five- and six-member benzo-fused heterocycles (9H-carbazole and phenanthridine) when an aromatic amide anion is competitively formed.

Carbanionic friedel-crafts equivalents. Regioselective directed Ortho and remote metalation-C-N cross coupling routes to acridones and dibenzo[b,f]azepinones

(Chemical Equation Presented) Carbanion-mediated general regioselective routes to acridones 4 (Table 2) and dibenzo[b,f]azepinones 20 (Table 4) are described. Buchwald-Hartwig C-N cross coupling of o-halo benzamides 1 with anilines 2 or 16, followed by simple N-methylation, dependably provides N-methyl diarylamines 3 (Table 1) and 18 (Table 3). Upon treatment with LDA, 3 and 18 are converted into acridones 4 and dibenzo[b,f]azepinones 20, respectively, in good to excellent yields with regioselectivity which depends upon the presence or absence of directed metalation groups (DMGs). Brief investigations as follows are described: the synthesis of desmethyl acridone 15 (Scheme 4), an attempt to effect a double-directed remote metalation sequence which leads only to a monocyclization product 13 (Scheme 3), and an analogous but nonregioselective route to a xanthone 22 and dibenzo[b,f]oxepinone 24 (Scheme 5). DFT calculations reveal low energy conformations for compounds 18b and 23 which account for product formation and indicate that the cyclization reactions are under kinetic control.

N-substituted azaheterocyclic carboxylic acids and alkylesters thereof

The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.

Directed ortho and remote Metalation - Cross coupling connections. Buchwald-Hartwig synthesis of 2-carbamoyl diarylamines. Regioselective anionic routes to acridones, oxindoles, dibenzo-[b,f]azepinones, and anthranilate esters

2-Carboxamido diarylamines 1f, 7, and 9, efficiently available by Buchwald-Hartwig C-N cross coupling reactions, serve as starting materials for new anionic routes to acridones 2d, oxindoles 10, dibenzo[b, f]azepinones 11, and anthranilate esters 8.

Heterocyclic compounds

The present invention relates to novel N-substituted azaheterocyclic carboxylic acids and esters thereof in which a substituted alkyl chain forms part of the N-substituent or salts thereof, to methods for their preparation, to compositions containing them, and to their use for the clinical treatment of painful, hyperalgesic and/or inflammatory conditions in which C-fibers play a pathophysiological role by eliciting neurogenic pain or inflammation.