We acknowledge with gratitude the NSERC Canada for support through the Discovery Grant program. We warmly thank Merck Frosst Canada for unrestricted grant support. J.P. would like to thank the NSERC for an Undergraduate Student Research Award (USRA).
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Communication
Carbamoyl Translocations by an Anionic ortho-Fries and Cumulenolate α-Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3- and 8-Carboxamides†
Article first published online: 11 FEB 2008
DOI: 10.1002/anie.200704360
Copyright © 2008 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim
Issue
Angewandte Chemie International Edition
Volume 47, Issue 11, pages 2097–2101, February 28, 2008
Additional Information
How to Cite
Macklin, Todd K., Panteleev, J. and Snieckus, V. (2008), Carbamoyl Translocations by an Anionic ortho-Fries and Cumulenolate α-Acylation Pathway: Regioselective Synthesis of Polysubstituted Chromone 3- and 8-Carboxamides. Angew. Chem. Int. Ed., 47: 2097–2101. doi: 10.1002/anie.200704360
- †
Publication History
- Issue published online: 22 FEB 2008
- Article first published online: 11 FEB 2008
- Manuscript Received: 21 SEP 2007
Funded by
- NSERC Canada
- Merck Frosst Canada
- NSERC
Keywords:
- anionic reactions;
- heterocycles;
- metalation;
- organolithium reagents;
- synthetic methods
Completing the circle: A synthesis of chromone 3- and 8-carboxamides (3 and 4) from 2-but-2-ynoyl aryl O-carbamates 1 has been achieved via common intermediate 2 in a regioselective manner. Repetitive metalation reactions and an iridium-catalyzed B2pin2 borylation lead to the construction of polysubstituted chromones, which are key components of many bioactive compounds.