Catalyst and solvent switched divergent C-H functionalization: oxidative annulation of -aryl substituted quinazolin-4-amine with alkynes

The development of site-selective C-H functionalizations/annulations is one of the most challenging practices in synthetic organic chemistry particularly for substrates bearing several similarly reactive C-H bonds. Herein, we describe catalyst and solvent controlled ortho / peri site-selective oxida...

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Bibliographic Details
Published in:Organic & biomolecular chemistry 2020-04, Vol.18 (16), p.332-337
Main Authors: Meesa, Siddi Ramulu, Naikawadi, Praveen Kumar, Gugulothu, Kishan, Shiva Kumar, K
Format: Article
Language:English
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Summary:The development of site-selective C-H functionalizations/annulations is one of the most challenging practices in synthetic organic chemistry particularly for substrates bearing several similarly reactive C-H bonds. Herein, we describe catalyst and solvent controlled ortho / peri site-selective oxidative annulation of C-H bonds of N -aryl substituted quinazolin-4-amines with internal alkynes. The ortho C-H selective annulation was observed using Pd-catalyst in DMF to give indole-quinazoline derivatives, while, Ru-catalyst in PEG-400 favoured the peri C-H bond annulation exclusively to furnish pyrido-quinazoline derivatives. Catalyst and solvent controlled ortho / peri site-selective oxidative annulation of C-H bonds of N -aryl substituted quinazolin-4-amines with internal alkynes.
ISSN:1477-0520
1477-0539
DOI:10.1039/d0ob00318b