Synthesis 2013; 45(16): 2328-2336
DOI: 10.1055/s-0033-1339191
paper
© Georg Thieme Verlag Stuttgart · New York

Selective Synthesis of Polysubstituted Dihydroquinolines and α,β-Unsaturated Amidines by a Catalytic Reaction of Ynamides with Ketimines

Yuusuke Kuroda
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8571, Japan   Fax: +81(75)7535604   Email: kay-t@pharm.kyoto-u.ac.jp
,
Naoya Shindoh
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8571, Japan   Fax: +81(75)7535604   Email: kay-t@pharm.kyoto-u.ac.jp
,
Yoshiji Takemoto
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8571, Japan   Fax: +81(75)7535604   Email: kay-t@pharm.kyoto-u.ac.jp
,
Kiyosei Takasu*
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8571, Japan   Fax: +81(75)7535604   Email: kay-t@pharm.kyoto-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 01 May 2013

Accepted after revision: 16 May 2013

Publication Date:
25 June 2013 (online)


Abstract

Ynamides reacted with benzophenone imines in the presence of triflic imide as a catalyst. Ynamides bearing a sulfonamide moiety gave the corresponding 2-amino-3,4-dihydroquinolines selectively in good to high yields. In contrast, yne-carbamates gave the corresponding α,β-unsaturated amidines exclusively. These methods permit simple preparation of sterically crowded polysubstituted quinolines and α,β-unsaturated amidines.

Supporting Information