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Published on: May 26, 2019
Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon
Sandip Balasaheb Wakade1,2, Dipak Kumar Tiwari1,2, Pothapragada S K Prabhakar Ganesh1
1Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology , Hyderabad 500007, India.
Abstract:
A transition-metal-free method for the construction of functionalized quinolines from readily available acetophenones and anthranils is reported. This one-pot reaction cascade involves in situ generation of α,β-unsaturated ketones from the acetophenone via one-carbon homologation by DMSO followed by the aza-Michael addition of anthranils and subsequent annulation. DMSO acted in this reaction not only as solvent but also as one carbon source, thus providing a highly atom-economical and environmentally benign approach for the synthesis of 3-substituted quinolines.
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