Iodine-promoted amide formation oxidative cleavage of indoles: novel quinazoline-4(3)-one and tryptanthrin syntheses.

A highly efficient method for the direct construction of amide bonds a selective cleavage of C-H and C[double bond, length as m-dash]C bonds in indole structures using an iodine-promoted approach was developed. Mechanistic studies indicated the formation of superoxide radicals obtained from molecular oxygen activation as a key intermediate step, which provided a precursor for subsequent oxidative ring-opening and intermolecular cyclization. A broad range of quinazolin-4(3)-ones and tryptanthrins were synthesized in moderate to good yields under mild and environmentally benign conditions.

Copper-catalyzed one-pot domino reactions C-H bond activation: synthesis of 3-aroylquinolines from 2-aminobenzylalcohols and propiophenones under metal-organic framework catalysis.

A Cu(OBA)(BPY) metal-organic framework was utilized as a productive heterogeneous catalyst for the synthesis of 3-aroylquinolines one-pot domino reactions of 2-aminobenzylalcohols with propiophenones. This Cu-MOF was considerably more active towards the one-pot domino reaction than a series of transition metal salts, as well as nano oxide and MOF-based catalysts. The MOF-based catalyst was reusable without a significant decline in catalytic efficiency.