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

Sandip Balasaheb Wakade, Dipak Kumar Tiwari, Pothapragada S. K. Prabhakar Ganesh, Mandalaparthi Phanindrudu, Pravin R. Likhar and Dharmendra Kumar Tiwari*

*Medicinal Chemistry and Biotechnology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500007, India, Email: dkt80.orggmail.com

S. B. Wakade, D. K. Tiwari, P. S. K. P. Ganesh, M. Phanindrudu, P. R. Likhar, D. K. Tiwari, Org. Lett., 2017, 19, 4948-4951.

DOI: 10.1021/acs.orglett.7b02429 (free Supporting Information)



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Abstract

A one-pot reaction cascade reaction enables a transition-metal-free construction of functionalized quinolines from readily available acetophenones and anthranils. The reaction 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 acts not only as solvent but also as one carbon source.

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proposed mechanism



Key Words

quinolines, potassium peroxydisulfate, multicomponent reactions


ID: J54-Y2017