Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
Synfacts 2010(2): 0161-0161
DOI: 10.1055/s-0029-1219124
DOI: 10.1055/s-0029-1219124
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Copper-Catalyzed Synthesis of Indole-2-carboxylates
Q. Cai*, Z. Li, J. Wei, C. Ha, D. Pei, K. Ding*
Guangzhou Institute of Chemistry, Guangzhou Science Park, P. R. of China
Further Information
Publication History
Publication Date:
21 January 2010 (online)
Significance
Reported is the straightforward synthesis of indole-2-carboxylate derivatives 3 from the reaction of 2-halo aryl aldehydes or ketones 1 with ethyl isocyanoacetate 2 under ligand-free copper(I) catalysis. The reaction proceeds at room temperature (for X = I) or elevated temperature (for X = Cl, Br) and is tolerant of both EDG and EWG on the aromatic ring. In general, higher yields were observed from ketone substrates compared to the aldehydes. The reaction was extended to the synthesis of 7-azaindole 4 and the unusual thienopyrroles 5 and 6 in good yield.