N-Amino-7-azaindole as the N,N'-Bidentate Directing Group: Ruthenium-Catalyzed Oxidative Annulation of N-(7-Azaindole)benzamides with Alkynes via C-H Bond Activation.

Abstract

We report a new application of N-amino-7-azaindole as a new bidentate-directing group for [Ru(p-cymene)Cl2]2-catalyzed C(sp2)-H alkenylation/annulation of N-(1H-pyrrolo[2,3-b]pyridin-1-yl)benzamides with internal alkynes to afford N-isoquinolono-7-azaindole via the formation of C-C and C-N bonds. The reaction shows a wide range of substrate scope with different symmetrical and unsymmetrical alkynes, affording the desired product in good to excellent yields. In the case of unsymmetrical alkynes, a highly regioselective product was obtained, which was confirmed by single-crystal X-ray crystallography. A new ruthenium-4-methyl-N-(1H-pyrrolo[2,3-b]pyridin-1-yl)benzamide complex was isolated, and its structure was confirmed by single-crystal X-ray crystallography.