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.org
gmail.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
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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
