Journal
ORGANIC LETTERS
Volume 11, Issue 4, Pages 1015-1018Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol802952e
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Funding
- National Natural Science Foundation of China [20711130229, 20872136]
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A convenient and efficient synthesis of spiro-fused pyrazolin-5-one N-oxides starting from readily available 1-carbamoyl-1-oximylcycloalkanes is developed. This general protocol features a novel and facile way for access to the five-membered azaheterocycles by formation of a new N-N single bond. The key cyclization step utilizes the formation of an N-oxonitrenium intermediate, mediated by the hypervalent iodine reagent PIFA, and its subsequent intramolecular trapping by the amide moiety under rather mild experimental conditions.
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