1701-57-1

Usage

Uses

2,3,4,5-Tetrahydro-1H-1-benzazepine is a reactant in the synthesis of adamantane derivatives as cannabinoid receptor 2 agonists.

InChI:InChI=1/C10H13N/c1-2-7-10-9(5-1)6-3-4-8-11-10/h1-2,5,7,11H,3-4,6,8H2

Upstream product

• 20642-90-4 1-methyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine 
• 4424-80-0 2,3,4,5-tetrahydro-1H-1-benzo[b]azepin-2-one 
• 542-69-8 1-iodo-butane 
• 6940-76-7 1-iodo-3-chloro-propane 
• 3349-64-2 1-tetralone oxime 
• 88920-00-7 2,3,4,5-tetrahydro-1-phenacyl-1H-benzazepine 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 209967-17-9 4-(2-aminophenyl)-1-butanol 
• 566913-12-0 4-(2-chlorophenyl)butylamine 
• 68253-36-1 1-tetralone oxime 
• 3749-11-9 1-methyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one 
• 857601-81-1 N-(3-methoxycarbonyl-propyl)-anthranilic acid methyl ester 
• 74799-85-2 N-(3-methoxycarbonyl-propyl)-N-methyl-anthranilic acid methyl ester 
• 134-20-3 2-carbomethoxyaniline 

Downstream Products

• 4425-15-4 4,5,6,7-tetrahydro-azepino[3,2,1-hi]indole-1,2-dione 
• 99293-85-3 N-(p-toluoyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 88920-00-7 2,3,4,5-tetrahydro-1-phenacyl-1H-benzazepine 
• 137975-23-6 1,2,3,4-Tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepine 
• 200729-53-9 (2,3,4,5-tetrahydro-1H-1-benzazepin-1-yl)-2-chloro-4-nitrobenzamide 
• 65596-57-8 1-formyl-2,3,4,5-tetrahydro-1H-1-benzazepine 
• 17422-54-7 8-nitro-2,3,4,5-tetrahydro-1H-benzo[b]azepine 
• 65797-77-5 α,α-bis(trifluoromethyl)-2,3,4,5-tetrahydro-1H-1-benzazepine-7-methanol 
• 99293-99-9 5-hydroxy-N-(p-toluoyl)-2,3,4,5-tetrahydro-1H-1-benzazepine 

Relevant academic research and scientific papers

Regioselectivity in Forming Dipole-Stabilized Anions. Sites of Metalation of Indolines, Tetrahydroquinolines, and Benzazepines Activated by N-Formimidoyl or N-Boc Groups

Metalation of the title compounds indicated that the formamidine-equipped indolines or 1,2,3,4-tetrahydroquinolines give rise solely to C-2 alkylation products (5,6) whereas the corresponding N-t-Boc systems give only ortho aryl alkylation (7,8).

Dehydrogenative and Redox-Neutral N-Heterocyclization of Aminoalcohols Catalyzed by Manganese Pincer Complexes

A new manganese catalyzed heterocyclization of aminoalcohols has been accomplished. A wide range of heterocycles were synthesized, including 1,2,3,4-tetrahydroquinolines, dihydroquinolinones, and 2,3,4,5-tetrahydro-1H-benzo[b]azepines. The reaction is performed under mild reaction conditions using air and moisture stable manganese catalysts. The desired heterocycles were obtained in good to excellent yields.

Tetrahydroquinoline-Capped Histone Deacetylase 6 Inhibitor SW-101 Ameliorates Pathological Phenotypes in a Charcot-Marie-Tooth Type 2A Mouse Model

Histone deacetylase 6 (HDAC6) is a promising therapeutic target for the treatment of neurodegenerative disorders. SW-100 (1a), a phenylhydroxamate-based HDAC6 inhibitor (HDAC6i) bearing a tetrahydroquinoline (THQ) capping group, is a highly potent and sel

Indirect reduction of CO2and recycling of polymers by manganese-catalyzed transfer hydrogenation of amides, carbamates, urea derivatives, and polyurethanes

The reduction of polar bonds, in particular carbonyl groups, is of fundamental importance in organic chemistry and biology. Herein, we report a manganese pincer complex as a versatile catalyst for the transfer hydrogenation of amides, carbamates, urea derivatives, and even polyurethanes leading to the corresponding alcohols, amines, and methanol as products. Since these compound classes can be prepared using CO2as a C1 building block the reported reaction represents an approach to the indirect reduction of CO2. Notably, these are the first examples on the reduction of carbamates and urea derivatives as well as on the C-N bond cleavage in amides by transfer hydrogenation. The general applicability of this methodology is highlighted by the successful reduction of 12 urea derivatives, 26 carbamates and 11 amides. The corresponding amines, alcohols and methanol were obtained in good to excellent yields up to 97%. Furthermore, polyurethanes were successfully converted which represents a viable strategy towards a circular economy. Based on control experiments and the observed intermediates a feasible mechanism is proposed.

Reaction of Vinyl Aziridines with Arynes: Synthesis of Benzazepines and Branched Allyl Fluorides

We report the cycloaddition between vinyl aziridines and arynes. Depending on the reaction conditions and the choice of the aryne precursor, the aziridinium intermediate can be trapped through two distinct mechanistic pathways. The first one proceeds through a formal [5+2] cycloaddition to furnish valuable multi-substituted benzazepines. In the second pathway, the aziridinium is intercepted by a fluoride ion to afford allylic fluorides in good yields. Both reactions proceed stereospecifically and furnish enantiopure benzazepines and allylic fluorides.

Formal Deoxygenative Hydrogenation of Lactams Using PNHP-Pincer Ruthenium Complexes under Nonacidic Conditions

A formal deoxygenative hydrogenation of amides to amines with RuCl2(NHC)(PNHP) (NHC = 1,3-dimethylimizadol-2-ylidene, PNHP = bis(2-diphenylphosphinoethyl)amine) is described. Various secondary amides, especially NH-lactams, are reduced with H2 (3.0-5.0 MPa) to amines at a temperature range of 120-150 °C with 1.0-2.0 mol % of PNHP-Ru catalysts in the presence of Cs2CO3. This process consists of (1) deaminative hydrogenation of secondary amides to generate primary amines and alcohols, (2) dehydrogenative coupling of the transient amines with alcohols to generate imines, and (3) hydrogenation of imines to give the formally deoxygenated secondary amine products.

Mild, Metal-Free Oxidative Ring-Expansion Approach for the Synthesis of Benzo[ b]azepines

Benzo[b]azepines are important structural motifs for the pharmaceutical industry. However, their syntheses are usually lengthy, involving several steps, transition-metal catalysts, and/or harsh conditions. A novel, general, mild, and metal-free oxidative ring expansion tandem reaction of hydroquinolines with TMSCHN2 as a versatile soft nucleophile to gain access to these valuable compounds in a simple and straightforward manner is presented.

Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines

The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.

Sodium Triethylborohydride-Catalyzed Controlled Reduction of Unactivated Amides to Secondary or Tertiary Amines

The first transition-metal-free catalytic protocol for controlled reduction of amide functions using cheap and bench-stable hydrosilanes as reducing agents has been established. By altering the hydrosilane and solvent, the new method enables the selective cleavage of unactivated C-O bonds in amides and allows the C-N bonds to selectively break via the deacylated cleavage. Overall, this novel process may offer a versatile alternative to current methodologies employing stoichiometric metal systems for the controlled reduction of carboxamides.

LIT-001, the First Nonpeptide Oxytocin Receptor Agonist that Improves Social Interaction in a Mouse Model of Autism

Oxytocin (OT) and its receptor (OT-R) are implicated in the etiology of autism spectrum disorders (ASD), and OT-R is a potential target for therapeutic intervention. Very few nonpeptide oxytocin agonists have currently been reported. Their molecular and in vivo pharmacology remain to be clarified, and none of them has been shown to be efficient in improving social interaction in animal models relevant to ASD. In an attempt to rationalize the design of centrally active nonpeptide full agonists, we studied in a systematic way the structural determinants of the affinity and efficacy of representative ligands of the V1a and V2 vasopressin receptor subtypes (V1a-R and V2-R) and of the oxytocin receptor. Our results confirm the subtlety of the structure-affinity and structure-efficacy relationships around vasopressin/oxytocin receptor ligands and lead however to the first nonpeptide OT receptor agonist active in a mouse model of ASD after peripheral ip administration.