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Issue 16, 2020
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Catalyst and solvent switched divergent C–H functionalization: oxidative annulation of N-aryl substituted quinazolin-4-amine with alkynes

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Abstract

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.

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

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Supplementary files

Article information


Submitted
13 Feb 2020
Accepted
27 Mar 2020
First published
27 Mar 2020

Org. Biomol. Chem., 2020,18, 3032-3037
Article type
Communication

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

S. R. Meesa, P. K. Naikawadi, K. Gugulothu and K. Shiva Kumar, Org. Biomol. Chem., 2020, 18, 3032
DOI: 10.1039/D0OB00318B

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