Photo-triggered self-catalyzed fluoroalkylation/cyclization of unactivated alkenes: synthesis of quinazolinones containing the CF₂R group

Abstract

A photo-triggered self-catalyzed fluoroalkylation/cyclization of quinazolinones containing unactivated alkenes with various fluoroalkyl bromides has been developed.

Synthesis of Polycyclic Quinazolinones through C(sp3)−H Functionalization of Inert Alkanes or Visible‐Light‐Promoted Oxidation Decarboxylation of N‐Hydroxyphthalimide Esters

“…According to the above experimental results and relevant literature, [11c–d,13−14] we come up with the feasible mechanism in Scheme 3. The reaction is initiated by the alkyl radical, which is caused by the α ‐C(sp 3 )−H cleavage of alkanes in the presence of DTBP under heating ( Path 1 ) or through electron transfer from the iodide to alkyl NHP‐esters 4 ( Path 2 ) [13–14] .…”

“…The alkyl radical is selectively added to the C=C bond of 1 a to generate the radical intermediate I . Then, I is added to the C=N bond of electron‐deficient heterocyclic ring to obtain the cyclization intermediate II , which then undergoes a 1,2‐hydrogen shift to produce carbon radical III [11c–d] . Eventually, the radical III experiences oxidation or deprotonation procedure to offer the desired product 3 [11c–d,13–14] …”

Greener Synthesis of Pyrroloquinazoline Derivatives: Recent Advances

“…The reaction scope consisted of a wide range of compounds, of which they have six‐membered ring, complex molecules such as cholesterol, and 17 examples consisting of five‐membered rings 69 with yields between 44–82 % (Scheme 37). [53] The method studied can be evidenced once it allowed to obtain dihydropyrrolo[2,1‐ b ]quinazolin‐9(1 H )‐ones 69 with simplicity of operation. The developed protocol tolerated several functional groups, thus reaching a wide scope, in addition to the fact that the reaction proceeded without photocatalyst and ligands.…”

Revisiting aromatic diazotization and aryl diazonium salts in continuous flow: highlighted research during 2001–2021

“…The strategy of spontaneous formation of free radicals by light-induced compounds has attracted great interest of scholars. 121…”