American Chemical Society
jo9b01598_si_001.pdf (5.76 MB)

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

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journal contribution
posted on 2019-09-25, 12:04 authored by Prateep Singh Sagara, Prem Felix Siril, Ponneri Chandrababu Ravikumar
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.