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 2007(7): 0687-0687
DOI: 10.1055/s-2007-968689
DOI: 10.1055/s-2007-968689
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York
Two-Carbon Annulation of N-Arylpyrroles to Benzoindoles and Pyrroloquinolines
D. G. Hulcoop, M. Lautens*
University of Toronto, Canada
Further Information
Publication History
Publication Date:
22 June 2007 (online)
Significance
Reported is a Pd-catalyzed synthesis of nitrogen-containing condensed heterocycles 3 which involves an annulation of N-arylpyrrole 1 with a strained alkene, followed by an in situ retro-Diels-Alder reaction of the intermediate 2. Achievement of heteroaromaticity appears to be the driving force. It is an interesting one-step process, based on the Catellani methodology (M. Catellani Synlett 2003, 298-313) to give heterocycles 3 in good to excellent yields. The functional group tolerance and scope of substrates were not sufficiently investigated.