Organic Letters
Organic Letters
5 years ago

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

Transition-Metal-Free Quinoline Synthesis from Acetophenones and Anthranils via Sequential One-Carbon Homologation/Conjugate Addition/Annulation Cascade
Dharmendra Kumar Tiwari, Pravin R. Likhar, Pothapragada S. K. Prabhakar Ganesh, Dipak Kumar Tiwari, Sandip Balasaheb Wakade, Mandalaparthi Phanindrudu
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.

Publisher URL: http://dx.doi.org/10.1021/acs.orglett.7b02429

DOI: 10.1021/acs.orglett.7b02429

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