Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 7, Pages 1805-1809Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201611024
Keywords
[4+2] annulation; heterocycles; naphthyridines; phenanthrolines; quinolones
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Funding
- NSFC [21672034]
- Shandong Normal University [108-100801]
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A silver-catalyzed chemoselective [4+2] annulation of aryl and heteroaryl isocyanides with -substituted isocyanoacetamides was developed for the facile and efficient synthesis of 2-aminoquinolones, naphthyridines, and phenanthrolines. A mechanism for this multistep domino reaction is proposed on the basis of a C-13-labeling experiment, according to which an unprecedented chemoselective heterodimerization of two different isocyanides generates an -amidoketenimine intermediate, which undergoes 1,3-amino migration to form an -imidoylketene, followed by 6 pi electrocyclization.
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