Rh-Catalyzed Cascade C-H Activation/Annulation of N-Hydroxybenzamides and Propargylic Acetates for Modular Access to Isoquinolones.

A sequential Rh(III)-catalyzed C-H activation/annulation of N-hydroxybenzamides with propargylic acetates leading to the formation of NH-free isoquinolones is described. This reaction proceeds through a sequential C-H activation/alkyne insertion/intramolecular annulation/N-O bond cleavage procedure, affording a broad spectrum of products with diverse substituents in moderate-to-excellent yields. Notably, this protocol features the simultaneous formation of two new C-C/C-N bonds and one heterocycle in one pot with the release of water as the sole byproduct.

Ru(II)/Ir(III)-Catalyzed C-H Bond Activation/Annulation of Cyclic Amides with 1,3-Diketone-2-diazo Compounds: Facile Access to 8H-Isoquinolino[1,2-b]quinazolin-8-ones and Phthalazino[2,3-a]cinnoline-8,13-diones.

Efficient access to 8H-isoquinolino[1,2-b]quinazolin-8-ones and phthalazino[2,3-a]cinnoline-8,13-diones through cyclic amide-directed Ru(II)/Ir(III)-catalyzed C-H bond activation, has been developed. Consecutive C-H bond activation, carbene insertion, and condensation annulation processes were realized, affording 8H-isoquinolino[1,2-b]quinazolin-8-one and phthalazino[2,3-a]cinnoline-8,13-dione derivatives in good-to-excellent yields under mild conditions, with H2O and N2 being generated as the only byproducts.