22190-47-2Relevant articles and documents
Photochemical C?H Hydroxyalkylation of Quinolines and Isoquinolines
Bieszczad, Bartosz,Perego, Luca Alessandro,Melchiorre, Paolo
supporting information, p. 16878 - 16883 (2019/11/13)
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.
Synthesis of some 6,7-dimethoxy isoquinolines containing benzoyl or alpha-hydroxybenzyl substitutions at position 1
Mahuzier,Hamon
, p. 687 - 690 (2007/10/04)
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