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Synthesis of 2,4-Diiodoquinolines via the Photochemical Cyclization of o-Alkynylaryl Isocyanides with Iodine

Takenori Mitamura and Akiya Ogawa*

*Department of Applied Chemistry, Graduate School of Engineering, Osaka Prefecture University, 1-1 Gakuen-cho, Nakaku, Sakai, Osaka 599-8531, Japan, Email: ogawachem.osakafu-u.ac.jp

T. Mitamura, A. Ogawa, X. Pan, J. Org. Chem., 2011, 76, 1163-1166.

DOI: 10.1021/jo1021772 (free Supporting Information)


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Abstract

Upon photoirradiation of o-alkynylaryl isocyanides in the presence of iodine, an intramolecular cyclization affords the corresponding 2,4-diiodoquinolines in good yields. 2,4-Diiodoquinolines can be employed in regioselective transition metal-catalyzed cross-coupling reactions.

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Key Words

Quinolines


ID: J42-Y2011-0330