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Synthesis of 4-Quinolones via a Carbonylative Sonogashira Cross-Coupling Using Molybdenum Hexacarbonyl as a CO Source

Linda Åkerbladh, Patrik Nordeman, Matyas Wejdemar, Luke R. Odell and Mats Larhed*

*Organic Pharmaceutical Chemistry, and §Science for Life Laboratory, Department of Medicinal Chemistry, BMC, Uppsala University, Box-574, SE-751 23 Uppsala, Sweden, Email: mats.larhedorgfarm.uu.se

L. Åkerbladh, P. Nordeman, M. Wdjdemar, L. R. Odell, M. Larhed, J. Org. Chem., 2015, 80, 1464-1471.

DOI: 10.1021/jo502400h (free Supporting Information)



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Abstract

Two different protocols for a palladium-catalyzed CO gas-free carbonylative Sonogashira/cyclization sequence enable the preparation of functionalized 4-quinolones from 2-iodoanilines and alkynes in the presence of molybdenum hexacarbonyl as a solid source of CO. The first method yields the cyclized products after only 20 min of microwave heating at 120°C. The second method is a one-pot two-step sequence which runs at room temperature.

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Key Words

4-quinolones


ID: J42-Y2015