62717-90-2

Upstream product

• 56030-50-3 (+)-(R)-1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydro-3H-benzazepine 
• 55171-76-1 3,4-dimethoxybicyclo[4.2.0]octa-1,3,5-trien-7-one 
• 24395-14-0 (R)-2-phenyl-N-tosylaziridine 
• 20012-08-2 1-phenyl-N-methyl-7,8-dimethoxy-1,2,4,5-tetrahydro-3H-benzazepine 
• 81633-75-2 (R)-3-cyano-2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-1H-3-benzazepine 

Downstream Products

• 132697-86-0 (R)-(-)-3-(2-Chlorethylcarbamoyl)-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepin 
• 81702-42-3 (+)-SKF 38393 hydrochloride 
• 139689-14-8 (R)-(+)-6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 62717-13-9 (R)-3-benzyl-2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine 
• 139689-19-3 (+)-6-Br-APB hydrobromide 
• 139689-16-0 (R)-(+)-3-allyl-6-bromo-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine 
• 139689-12-6 (R)-(+)-3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 
• 139689-08-0 (R)-(+)-3-allyl-7,8-dimethoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine hydrochloride 
• 62717-92-4 (R)-3-benzyl-2,3,4,5-tetrahydro-7,8-dimethoxy-1-phenyl-1H-3-benzazepine 

Relevant academic research and scientific papers

A ring expansion strategy towards diverse azaheterocycles

The development of innovative strategies for the synthesis of N-heterocyclic compounds is an important topic in organic synthesis. Ring expansion methods to form large N-heterocycles often involve the cycloaddition of strained aza rings with π bonds. However, in some cases such strategies suffer from some limitations owing to the difficulties in controlling the regioselectivity and the accessibility of specific π-bond synthons. Here, we report the development of a general ring expansion strategy that involves a formal cross-dimerization between three-membered aza heterocycles and three- and four-membered-ring ketones through synergistic bimetallic catalysis. These formal cross-dimerizations of two different strained rings are efficient and scalable, and provide a straightforward and broadly applicable means of assembling diverse N-heterocycles, such as 3-benzazepinones, dihydropyridinones and uracils, which are versatile units in numerous drugs and biologically active compounds. Preliminary mechanistic studies revealed that the C–C bond of strained ring ketones is first cleaved by the Pd0 species during the reaction. [Figure not available: see fulltext.].

Stereoisomeric probes for the D1 dopamine receptor: synthesis and characterization of R-(+) and S-(-) enantiomers of 3-allyl-7,8-dihydroxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine and its 6-bromo analogue.

Substituted 1-phenyl-3-benzazepines (e.g., SKF 38393 and fenoldopam) exhibit stereoselectivity in moderately high-affinity binding to and partial agonist activation of D1 dopamine receptors. The 3-allyl (APB) and the 3-allyl-6-chloro (6-Cl-APB) analogues

Absolute stereochemistry and dopaminergic activity of enantiomers of 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine

Resolution of the unique dopamine receptor agonist 2,3,4,5-tetrahydro-7,8-dihydroxy-1-phenyl-1H-3-benzazepine (1) was achieved by a stereospecific multistep conversion of the readily separated enantiomers of its O,O,N-trimethylated diffractometric analysi