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Updated: Jan 15, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
DABCO-directed EDA-complex mediated regioselective C4-sulfonylation of quinoline N-oxide
Dinabandhu Barik1, Pritishree Panigrahi1, Supriya Manna1
1Department of Chemistry, Indian Institute of Technology Guwahati, 781039, Assam, India. patel@iitg.ac.in.
Abstract:
A visible light-mediated, electron donor-acceptor (EDA) complex-enabled regioselective C4-sulfonylated quinoline N-oxide is presented. In this transformation, organic thiosulfonates serve as a sulfonyl radical (RSO2˙) precursor, enabling the formation of either C4 sulfonylated quinoline N-oxide or C4 sulfonylated quinoline (deoxygenated) by slight variation of the solvent composition. The base DABCO acts as an electron donor, forming an EDA complex with the acceptor thiosulfonate, generating an RSO2˙. DABCO also serves as a transient directing group in dictating the C4-regioselectivity by temporarily blocking the more reactive C2 site.
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