Journal
ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 22, Pages 3586-3599Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600503
Keywords
annulation; diamines; diazodicarbonyls; heterocycles; N-H insertion
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Funding
- National Research Foundation of Korea (NRF) grant - Korea government (MSIP) [NRF-2014R1A2A1A11052391]
- Nano Material Technology Development Program [2012M3A7B4049675, 2014R1A6A1031189]
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A novel and facile iron-catalyzed tandem annulation of o-phenylenediamines and diazocarbonyls in water for the construction of polyfunctionalized quinoxalines has been developed. The key strategy includes the one-pot domino N-H insertion, cyclization, and oxidation reactions. This protocol offers a safe and mild synthetic approach to access a variety of quinoxaline derivatives in high yields. This methodology also allows the formation of biologically interesting pyrazines and benzoquinoxalines.
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