Abstract
A simple and efficient metal-free arylation of imidazo[1,2-a]pyridines at the C-3 position with arylhydrazine has been achieved at room temperature under ambient air conditions. Various 2,3-disubstituted imidazopyridines and imidazothiazoles were synthesized with high yields. The present methodology demonstrates the usefulness of commercially available aryl hydrazine as an arylating agent.
Highlights
The development of efficient methodologies for the arylation of biological active heterocycles has been of great importance over the years.[1]
The present methodology offers a practical route for the synthesis of various 2,3-disubstituted imidazo[1,2-a] pyridines with a wide range of functional groups
Reagents were purchased from commercial sources and used without further puri cation. 1H and 13C{1H} nuclear magnetic resonance (NMR) spectra were determined on a 400 MHz spectrometer. 1H NMR spectra were determined on a 400 MHz spectrometer as solutions in CDCl3
Summary
The development of efficient methodologies for the arylation of biological active heterocycles has been of great importance over the years.[1]. The synthesized product was further functionalized employing Sonogashira and Suzuki coupling reactions (Scheme 6).8c 6-Bromo-2,3-diphenylimidazo[1,2-a]pyridine (3ra) was reacted with ethynylbenzene (Scheme 6, eqn A) to afford 2,3-diphenyl-6(phenylethynyl)imidazo[1,2-a]pyridine (5) in excellent yield (95%).
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