69743-45-9

Upstream product

• 42600-77-1 N-(3,4-dimethoxyphenethyl)cyclohexanecarboxamide 
• 72106-00-4 (rac)-1-cyclohexyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 120-20-7 2-(3,4-dimethoxyphenyl)-ethylamine 
• 2043-61-0 cyclohexanecarbaldehyde 

Downstream Products

• 1068158-43-9 (S)-6,7-dimethoxy-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline 
• 128425-94-5 1,5,6,10b-Tetrahydro-10b-hydroxy-8,9-dimethoxy-1,1-pentamethylene-3H-oxazolo<4,3-a>isoquinolin-3-one 
• 128425-96-7 1,5,6,10b-Tetrahydro-8,9-dimethoxy-1,1-pentamethylene-3H-oxazolo<4,3-a>isoquinolin-3-one 
• 128425-97-8 1-(1-Hydroxycyclohexyl)-1,2,3,4-tetrahydro-6,7-dimethoxyisoquinoline 
• 128425-93-4 Phenyl 1-Cyclohexylidene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 
• 128425-95-6 Methyl 1-Cyclohexylidene-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline-2-carboxylate 

Relevant academic research and scientific papers

Driving Recursive Dehydration by PIII/PV Catalysis: Annulation of Amines and Carboxylic Acids by Sequential C-N and C-C Bond Formation

A method for the annulation of amines and carboxylic acids to form pharmaceutically relevant azaheterocycles via organophosphorus PIII/PV redox catalysis is reported. The method employs a phosphetane catalyst together with a mild bromenium oxidant and terminal hydrosilane reductant to drive successive C-N and C-C bond-forming dehydration events via the serial action of a catalytic bromophosphonium intermediate. These results demonstrate the capacity of PIII/PV redox catalysis to enable iterative redox-neutral transformations in complement to the common reductive driving force of the PIII/PV couple.

Bioinspired aerobic oxidation of secondary amines and nitrogen heterocycles with a bifunctional quinone catalyst

Copper amine oxidases are a family of enzymes with quinone cofactors that oxidize primary amines to aldehydes. The native mechanism proceeds via an iminoquinone intermediate that promotes high selectivity for reactions with primary amines, thereby constraining the scope of potential biomimetic synthetic applications. Here we report a novel bioinspired quinone catalyst system consisting of 1,10-phenanthroline-5,6-dione/ZnI2 that bypasses these constraints via an abiological pathway involving a hemiaminal intermediate. Efficient aerobic dehydrogenation of non-native secondary amine substrates, including pharmaceutically relevant nitrogen heterocycles, is demonstrated. The ZnI2 cocatalyst activates the quinone toward amine oxidation and provides a source of iodide, which plays an important redox-mediator role to promote aerobic catalytic turnover. These findings provide a valuable foundation for broader development of aerobic oxidation reactions employing quinone-based catalysts.