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Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon Homologation/Conjugate Addition/Annulation Cascade

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journal contribution
posted on 07.09.2017, 14:20 by Sandip Balasaheb Wakade, Dipak Kumar Tiwari, Pothapragada S. K. Prabhakar Ganesh, Mandalaparthi Phanindrudu, Pravin R. Likhar, Dharmendra Kumar Tiwari
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.