22190-47-2

Upstream product

• 193551-54-1 (2-Bromo-phenyl)-(6,7-dimethoxy-isoquinolin-1-yl)-methanone 
• 260552-69-0 (±)-(2-bromophenyl)(6,7-dimethoxyisoquinolin-1-yl)methanol 
• 15248-39-2 6,7-dimethoxyisoquinoline 

Relevant academic research and scientific papers

Photochemical C?H Hydroxyalkylation of Quinolines and Isoquinolines

We report herein a visible light-mediated C?H hydroxyalkylation of quinolines and isoquinolines that proceeds via a radical path. The process exploits the excited-state reactivity of 4-acyl-1,4-dihydropyridines, which can readily generate acyl radicals upon blue light absorption. By avoiding the need for external oxidants, this radical-generating strategy enables a departure from the classical, oxidative Minisci-type pattern and unlocks a unique reactivity, leading to hydroxyalkylated heteroarenes. Mechanistic investigations provide evidence that a radical-mediated spin-center shift is the key step of the process. The method's mild reaction conditions and high functional group tolerance accounted for the late-stage functionalization of active pharmaceutical ingredients and natural products.

Aryl radical cyclizations of 1-(2′-bromobenzyl)isoquinolines with AIBN-Bu3SnH: Formation of aporphines and indolo[2,1-a]isoquinolines

(matrix presented) Radical cyclization of alkoxy-substituted 1-(2′-bromobenzyl)-3,4-dihydroisoquinolines 1 with AIBN-Bu3SnH gave 6a,7-dehydroaporphines 2 preferentially. A steric repulsion between the respective alkoxy groups at the 7- and 3′-positions gave 5,6-dihydroindolo[2,1-a]isoquinolines 3 in a disfavored 5-endo cyclization mode. Radical cyclizations of the related substrates, such as 1-(2′-bromobenzoyl)isoquinolines or 1-(2′-bromo-α-hydroxybenzyl)isoquinolines, were also found to give the corresponding oxoaporphines or oxyaporphines.