1132765-74-2

Upstream product

• 1745-07-9 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 5720-05-8 4-methylphenylboronic acid 
• 624-31-7 4-tolyl iodide 
• 106-38-7 para-bromotoluene 
• 2328-12-3 6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline monohydrochloride 

Downstream Products

• 1132765-79-7 6,7-dimethoxy-1-(nitromethyl)-2-(p-tolyl)-1,2,3,4-tetrahydroisoquinoline 

Relevant academic research and scientific papers

Porphyrin-Catalyzed Oxidation of N-Substituted Tetrahydroisoquinolines to Dihydroisoquinolones

A visible-light-induced direct α-oxygenation of N-substituted 1,2,3,4-Tetrahydroisoquinoline derivatives has been successfully developed. Tetraphenylporphyrinatozinc(II) has been identified as an effective and inexpensive photocatalyst for this transformation with a wide range of substrates. This protocol provides a convenient route to the desired products in moderate to good yields at room temperature under air.

Reactions Catalysed by a Binuclear Copper Complex: Relay Aerobic Oxidation of N-Aryl Tetrahydroisoquinolines to Dihydroisoquinolones with a Vitamin B1 Analogue

N-Aryl tetrahydroisoquinolines were oxidised to dihydroisoquinolones through the relay catalysis of a binuclear paddle-wheel copper complex and a vitamin B1 analogue with oxygen as oxidant. Mechanistic studies revealed that the copper catalyst oxidises amines to the corresponding iminium salts, which are then oxygenated to lactam products by catalysis of the vitamin B1 analogue.

Visible light catalyzed Mannich reaction between: Tert -amines and silyl diazoenolates

The present work documents the α-C-H functionalization of tertiary amines via the visible light catalyzed Mannich reaction with silyl diazoenolates. The reaction takes place at room temperature with an organic dye, Rose Bengal, as a photocatalyst and oxygen as the oxidant. The resulting multifunctional products bearing an α-diazo-β-keto group undergo Rh-carbenoid mediated cyclization, affording stable ammonium ylides in high yields.

Bifunctional organic sponge photocatalyst for efficient cross-dehydrogenative coupling of tertiary amines to ketones

A novel bifunctional organic sponge photocatalyst can enable the efficient coupling of tertiary amines with ketones in water. The asymmetric transformation can be also achieved by using this sponge photocatalyst.

Enantioselective oxidative cross-dehydrogenative coupling of tertiary amines to aldehydes

Cooperative catalysts: An enantioselective and direct oxidative coupling of aldehydes to tertiary amines to give β-amino alcohols is described. Catalyzed by copper(II), the reaction proceeds to give a racemic mixture of products; however, by using a combination of copper(II) and a chiral amine catalyst, the reaction gives the desired products with high enantioselectivity (see scheme).

Facile synthesis of vicinal diamines via oxidation of N-phenyltetrahydroisoquinolines with DDQ

The oxidation of N-phenyltetrahydroisoquinolines occurs rapidly with DDQ. Under ambient conditions and in the presence of nitromethane, the corresponding β-nitroamine derivatives are isolated in good to excellent yields. Variation in the electronic nature of the isoquinoline and the N-phenyl substituent showed that a broad range of substituents are tolerated, with electronic communication between the isoquinoline aromatic ring and the C1 carbon being stronger than with the N-aryl ring. Reduction of the β-nitroamines to the corresponding novel chiral vicinal diamines are straightforward. Examination of the reaction by 1H NMR spectroscopy suggested that the reaction proceeds via an iminium ion, which then reacts with nitromethane upon work-up. This information was used to shorten the required reaction time.