23818-73-7

Upstream product

• 15248-39-2 6,7-dimethoxyisoquinoline 
• 108-88-3 toluene 
• 100-44-7 benzyl chloride 
• 4722-08-1 3,4-dimethoxy-β-methoxybenzeneethanamine 
• 57542-91-3 phenyl-acetic acid-(3,4,β-trimethoxy-phenethylamide) 
• 10025-87-3 trichlorophosphate 
• 71-43-2 benzene 
• 3423-37-8 1-benzyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline 
• 4876-00-0 1-benzyl-6,7-dimethoxy-3,4-dihydro-isoquinoline 
• 1370593-50-2 C₂₅H₂₄O₃ 
• 1370593-37-5 4,5-dimethoxy-2-(3-phenylallyl)benzaldehyde 

Downstream Products

• 20359-09-5 (6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)(phenyl)methanone 

Relevant academic research and scientific papers

Ruthenium-Mediated Dual Catalytic Reactions of Isoquinoline via C?H Activation and Dearomatization for Isoquinolone

We have unraveled the ruthenium-promoted prototype reaction based on C(sp2)?C(sp3) bond formation through the reigoselective C?H activation of isoquinoline and pyridine derivatives with various alkyl halides, leading to 1-substituted isoquinoline products in good yield. This C?H catalytic reaction did not rely on chelation assistance of the directing group of the substrates. The dimer [RuCl2(p-cymene)]2in combination with an N-heterocyclic carbene ligand, adamantanecarboxylic acid and K2CO3base in N-methyl-2-pyrrolidone solution at 150 °C are the best conditions. Simultaneously, we are also able to chemically tune the reaction mode to dearomatization by adding water, leading to isoquinolone products. This reaction methodology is not suitable for other nitrogen-containing heteroarenes such as pyridazines and pyrimidines. (Figure presented.).

C1-Benzyl and benzoyl isoquinoline synthesis through direct oxidative cross-dehydrogenative coupling with methyl arenes

An oxidative cross-dehydrogenative coupling (CDC) of isoquinolines with methyl arenes has been developed, allowing for the facile synthesis of a broad range of structurally diverse C1-benzyl and -benzoyl isoquinolines. The direct use of readily available methyl arenes as coupling partners avoids unproductive steps for preactivating the functional group installation, and is therefore attractive. The method exhibits excellent chemoselectivity, affording exclusive benzylated products in the presence of DTBP and a catalytic amount of Y(OTf)3, and yielding benzoylated ones with TBHP and a catalytic amount of MnO2.

Facile synthesis of substituted isoquinolines

A facile three-step protocol toward methoxy isoquinolines 7 starting with substituted 2-allylbenzaldehydes 9 was described. The overall synthetic process of skeleton 7 was carried out using the Grignard addition, PCC-oxidation, and one-pot oxidative cleavage of the olefinic group of skeleton 9 with OsO 4-NaIO4 followed by the condensation of the resulting 1,5-dicarbonyl compounds with NH4OAc. Skeleton 9 was prepared in high yield via the known Claisen rearrangement of skeleton 8 and O-methylation. Papaverine 2 is also synthesized via the simple three-step synthetic protocol.

Photoaromatization of 1,2,3,4-tetrahydroisoquinolines

Irradiation of 1,2,3,4-tetrahydroisoquinolines (1a-d) in the presence of phenanthraquinone or benzophenone affords the corresponding isoquinolines (3a-d) in about 50percent yield.

New structural analogs of papaverine: 3 benzyl 6,7 dimethoxy (di and tetrahydro) isoquinolines

Syntheses of 3 benzyl 3,4 dihydroisoquinolines by cyclisation of a N acyl α benzylhomoveratrylamine by means of polyphosphoric acid ester, in boiling toluene, gave yields between 60 and 90%. While the hydrogenation of these dihydroisoquinolines to tetrahydroisoquinolines with an alkaline borohydride gave satisfactory result, their dehydrogenation into isoquinolines could not be accomplished. Pharmacological properties of the hydrobromides or hydrochlorides of the bases of the two series of the aforementioned 3 benzylisoquinolines and comparison of their activities with those of papaverine and the analogues 1 and 4 benzylisoquinolines are reported.