Transition metal-catalyzed reaction of N-propargyl anilines: Synthesis of heteroaromatic compounds

ORGN 572

Yuji Hanzawa, hanzaway@ac.shoyaku.ac.jp, Ayumi Kanno, and Akio Saito. Laboratory of Organic Reaction Chemistry, Showa Pharmaceutical University, 3-3165 Higashi-tamagawagakuen, Machida, Tokyo, 194-8543, Japan

Rh(I)-Catalyzed reactions of N-propargyl aniline derivatives afforded 2,3-disubstituted indole compounds in good yields under mild conditions. The indoles are formed via o-allenyl aniline intermediate generated through the Rh(I)-catalyzed aromatic N-Claisen rearrangement of the N-propargyl aniline. The scope and limitations of the reaction are disclosed.

 

 

Physical Organic Chemistry, Metal-Mediated Reactions, Asymmetric Reactions and Syntheses
8:00 PM-10:00 PM, Tuesday, August 21, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007