期刊
ADVANCED SYNTHESIS & CATALYSIS
卷 360, 期 16, 页码 3157-3163出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201800407
关键词
heterocycles; furoxan; pyridine; rearrangement; N-oxide oxygen transfer
资金
- Russian Science Foundation [14-50-00126]
A new approach to hetaryl carbamates through a tandem condensation/rearrangement reaction of 2-aminohetarene N-oxides was developed. The developed reaction is suitable for both five- and six-membered heterocycles and proceeds through the condensation of 2-aminohetarene N-oxide with trimethyl orthoformate followed by intramolecular N-oxide oxygen transfer. For five-membered hetarene N-oxides (furoxans), the intramolecular rearrangement is catalyzed by a cyanide anion, while for six-membered hetarene N-oxides (azines), Lewis acid catalysis is sufficient. The developed protocol is characterized by operational simplicity and high efficiency, resulting in carbamoyl derivatives in good and high yields.
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