Divergent Construction of Diverse Scaffolds through Catalyst‐Controlled C−H Activation Cascades of Quinazolinones and Cyclopropenones

Abstract

A transition-metal-catalyzed CÀ H activation cascade strategy to rapidly construct diverse quinazolinone derivatives in a one-pot manner is reported. The catalysts play an important role in the different transformations. Additionally, the procedure is scalable, proceeds with high efficiency and good chemo-/regio-selectivity, and tolerates a range of functional groups.

Heterocycles from cyclopropenones

“…120 Moreover, in 2021, Shi et al succeeded to synthesize the heterocyclic substituted 2-phenyl-10 0 H-spiro[indene-1,12 0 -isoindolo[1,2-b]quinazolin]-10 0 -ones 133a-j in 58-87% yield by reacting 2-phenylquinazolin-4-ones 132a-j with cyclopropenones 1 in reuxing DCE for 24 h, and a (cymene)ruthenium dichloride dimer [Ru(p-cymene)Cl] 2 was used as a metal catalyst (Scheme 83). 121 Shi et al Reuxing 137 with 2,3-substituted cyclopropenones 1 in DCM yielded quinazoline derivatives 138a-i in 44-85% yield. The reaction was catalyzed using (Cp*RhCl 2 ) 2 and AgSbF 6 , as shown in Scheme 85.…”

“…Moreover, in 2021, Shi et al succeeded to synthesize the heterocyclic substituted 2-phenyl-10′ H -spiro[indene-1,12′-isoindolo[1,2- b ]quinazolin]-10′-ones 133a–j in 58–87% yield by reacting 2-phenylquinazolin-4-ones 132a–j with cyclopropenones 1 in refluxing DCE for 24 h, and a (cymene)-ruthenium dichloride dimer [Ru( p -cymene)Cl] 2 was used as a metal catalyst (Scheme 83). 121…”

“…The reaction was performed in trifluoroethanol (TFE) at 110 °C for 48 h. Subsequently, treatment of compound 135a–f with trifluoroacetic acid (TFA) at 140 °C and in the presence of Rh[Cp*(OAc)] and Ag 2 O yielded compounds 136a–f (Scheme 84). 121…”

Ir(III)-Catalyzed Dual C–H Activation of 2-Aryl Phthalazinediones and 3-Aryl-2H-benzo[e][1,2,4]thiadiazine-1,1-dioxides for the Construction of Spiro-Fused Cyclic Frameworks

“…Based on previous reports, a plausible mechanism is proposed in Scheme . Initially, a monomeric Ir­(III) complex is formed from the dimeric [Cp*IrCl 2 ] 2 and AgSbF 6 .…”