Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 141, Issue 15, Pages 6247-6253Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.8b13481
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Funding
- National Institutes of Health [DK072517, DK067003]
- NSF XSEDE program [CHE030089]
- National Science Foundation [DBI722538, CHE9808183]
- NIH National Institute of Environmental Health Sciences [ES00570713]
- UC Davis Tara K. Telford CF Fund
- UC Davis Dissertation Year Fellowship
- R. Bryan Miller Graduate Fellowship
- UC Davis Provost's Undergraduate Fellowship
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The Cadogan cyclization is a robust but harsh method for the synthesis of 2H-indazoles, a valuable class of nitrogen heterocycles. Although nitrene generation by exhaustive deoxygenation is widely accepted as the operating mechanism in the reductive cyclization of nitroaromatics, non-nitrene pathways have only been theorized previously. Here, 2H-indazole N-oxides were synthesized through an interrupted Cadogan/Davis-Beirut reaction and are presented as direct evidence of competent oxygenated intermediates; mechanistic implications for both reactions are discussed. Isolation and characterization of these N-oxides enabled a formal Cadogan cyclization at room temperature for 2H-indazole synthesis.
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