20011-90-9

Usage

Synthesis Reference(s)

Journal of the American Chemical Society, 77, p. 675, 1955 DOI: 10.1021/ja01608a040

InChI:InChI=1/C14H11NO/c16-14-9-10-5-1-2-6-11(10)12-7-3-4-8-13(12)15-14/h1-8H,9H2,(H,15,16)

Upstream product

• 406198-23-0 (2'-cyanomethylbiphenyl-2-yl)carbamic acid tert-butyl ester 
• 17294-89-2 2'-nitro-biphenyl-2-carboxylic acid 
• 1440427-23-5 N-(2'-methyl-[1,1'-biphenyl]-2-yl)pivalamide 
• 1203-41-4 2-(2-methylphenyl)aniline 
• 57486-69-8 methyl 2-(2-bromophenyl)acetate 
• 191171-55-8 2-anilineboronic acid pinacol ester 
• 540803-89-2 2-(2-iodophenyl)-N-phenylacetamide 
• 591-50-4 iodobenzene 
• 71237-36-0 2'-nitrobiphenyl acid chloride 
• 161117-84-6 tert-butyl 2-iodophenylcarbamate 
• 615-36-1 2-bromoaniline 
• 40400-15-5 2-(2-iodophenyl)acetonitrile 
• 683277-83-0 (2'-azido-biphenyl-2-yl)-acetic acid pentafluorophenyl ester 
• 325141-76-2 2-{2'-amino-[1,1'-biphenyl]-2-yl}acetonitrile 

Downstream Products

• 209984-30-5 N-methyl-5H-dibenzo[b,d]azepin-6(7H)-one 
• 847926-88-9 (S)-7-amino-5H-dibenzo[b,d]azepin-6(7H)-one 
• 847926-45-8 7-amino-5-(4-methoxybenzyl)-5H dibenzo[b,d]azepin-6(7H)-one 
• 847926-44-7 5-(4-methoxybenzyl)-5H-dibenzo[b,d]azepin-6(7H)-one 
• 111-25-1 1-bromo-hexane 
• 209984-97-4 5-amino-7-phenbutyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 
• 209994-99-0 7-(L-alaninyl)-amino-5-methyl-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 
• 209984-31-6 7-methyl-5-oximo-5,7-dihydro-6H-dibenz[b,d]azepin-6-one 
• 213024-76-1 7-amino-5-methyl-5H-dibenzo[b,d]azepin-6(7H)-one hydrochloride 

Relevant academic research and scientific papers

Atropisomeric properties of 7-, 8-, and 9-membered-ring dibenzolactams: Conformation, thermal stability, and chemical reactivity

The atropisomeric enantiomers of 7-, 8-, and 9-membered-ring dibenzolactams were separated by using chiral HPLC, and their stereochemistries were clarified by using X-ray crystallographic analysis. The atropisomers showed high stereochemical stability with the 8-membered ring being the most stable. In 7- and 8-membered dibenzolactams, highly stereoselective C7-methylation proceeded from the lower side of the ring to provide the products with a C7-methyl group in the pseudoaxial orientation, which converted to thermodynamically more stable isomers with the pseudoequatorial C7-methyl group. In 9-membered dibenzolactam, C7-methylation occurred from the opposite (upper) side of the ring to provide a thermodynamically stable product with the pseudoequatorial C7-methyl group.

Organocatalytic synthesis of (Het)biaryl scaffoldsviaphotoinduced intra/intermolecular C(sp2)-H arylation by 2-pyridone derivatives

A uniqueN,O-bidentate ligand 6-oxo-1,6-dihydro-pyridone-2-carboxylic acid dimethylamide (L1) catalyzed direct C(sp2)-H (intra/intermolecular) arylation of unactivated arenes has been developed to expedite access to (Het)biaryl scaffolds under UV-irradiation at room temperature. The protocol tolerated diverse functional groups and substitution patterns, affording the target products in moderate to excellent yields. Mechanistic investigations were also carried out to better understand the reaction pathway. Furthermore, the synthetic applicability of this unified approach has been showcasedviathe construction of biologically relevant 4-quinolone, tricyclic lactam and sultam derivatives.

Crystallization-Induced Dynamic Resolution toward the Synthesis of (S)-7-Amino-5H,7H-dibenzo[b,d]-azepin-6-one: An Important Scaffold for γ-Secretase Inhibitors

An enantioselective synthesis of (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one (S-1) is described. The key step in the sequence involved crystallization-induced dynamic resolution (CIDR) of compound 7 using Boc-d-phenylalanine as a chiral resolving agent and

Intramolecular C(sp3)-N coupling by oxidation of benzylic C,N-dianions

What a couple! An intramolecular, C(sp3)-N coupling to afford azacycles is reported. This reaction proceeds through the oxidation of benzylic C,N-dianions with iodine and builds on an earlier discovery during the synthesis of the natural produc

An efficient one-pot microwave assisted synthesis of dibenzoazepinones

Microwave assisted one-pot synthesis of substituted 5H-dibenzo[b,d]azepin- 6(7H)-ones from 2-(2-bromophenyl)acetic acid esters and 2-aminophenyl boronates has been described. This approach gives direct access to seven membered lactams with a shorter cycle time of synthesis and high yields.

KOtBu mediated synthesis of phenanthridinones and dibenzoazepinones

Synthesis of substituted phenanthridinones and dibenzoazepinones has been realized from 2-halo-benzamides in the presence of potassium tert-butoxide and a catalytic amount of 1,10-phenanthroline or AIBN. This new carbon-carbon bond forming reaction gives direct access to various biaryl lactams containing six- and seven-membered rings chemoselectively. Carbon-carbon coupling seems to proceed by the generation of a radical in the amide ring which leads to C-H arylation of aniline.

Improved synthesis of (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one, a building block for γ-secretase inhibitors

An improved synthesis of (S)-7-amino-5H,7H-dibenzo[b,d]azepin-6-one (1), involving a selective crystallization of epimeric menthylcarbamates for the resolution step followed by simultaneous cleavage of the carbamate and the lactam protecting group is desc

Atropisomeric properties of the dibenzo[b,d]azepin-6-one nucleus

(Figure Presented) Dibenzo[b,d]azepin-6-ones (2a,b) were separated by chiral HPLC into the aR- and aS-atropisomers with high stereochemical stability, and methylation at C7 of 2a stereoselectively gave the (aR*,7R*) isomer (4a), which converted to the the

PROCESS FOR PREPARATION OF ENANTIOMERICALLY PURE COMPOUNDS

The invention relates to a process for the optical resolution of a dibenzo[b,d]azepinone derivative of formula II, wherein R1 is hydrogen or halogen and R2 is either C1-4-alkyl optionally substituted with C3-7-c