Visible-light promoted intramolecular carboamination of alkynes for the synthesis of oxazolidinone-fused isoquinolinones

Abstract

An efficient method for the synthesis of isoquinolinone derivatives via photopromoted carboamination of alkynes is developed. Starting from the readily available propargyl alcohol derivatives, the polycyclic isoquinolinone derivatives could be...

Photocatalysis as a green alternative toolkit for the construction of nitrogen-enriched heterocycles via the direct and indirect activation of alkynes/alkenes

“…This study produced polycyclic isoquinolinone derivatives ( 290 ) with good aryl and heterocycle tolerance beginning from easily accessible propargyl alcohol derivatives (Table 10J). 68 When exposed to blue light, excited Ir( iii ) ( PC23* ) could cleave the N–O bond of 289 via reduction and produce intermediate nitrogen radical species 332 . Intramolecular cyclization and deprotonation steps produced the required oxazolidinone-fused isoquinolinone ( 290 ) with good regioselectivity (Fig.…”

Photoredox-catalyzed oxytrifluoromethylation of alkenes toward CF3-containing five-membered cyclic carbonates

“…In our previous work, 11 we achieved the non-activated C(sp 3 )–H oxygenation of carbamates to form alkyl-substituted cyclic carbonates through photoinduced nitrogen radical-mediated 1,5-HAT. Inspired by a series of elegant photocatalytic CF 3 radical-mediated addition/cyclization reactions used to synthesize various biologically meaningful CF 3 -containing oxygen heterocycles, 12,13 we envision the synthesis of functionalized cyclic carbonates through the addition of CF 3 radical to allyl carbamates, followed by the oxidative radical-polar crossover and nucleophilic cyclization.…”

Photoredox-Enabled Deconstructive [5 + 1] Annulation Approach to Isoquinolones from Indanones in Water

“…Therefore, extensive efforts to develop synthetic strategies for their construction have emerged . Transition-metal-catalyzed C–H/N–H annulation of aromatic amides with alkynes or other alkyne surrogates has become one of the most straightforward methods (Scheme b, left) due to its atom- and step-economical nature. An unexplored approach involves a [5 + 1] disconnection, (Scheme b, right), which makes use of a nitrogen insertion into indanones.…”