ChemInform Abstract: Non-photochemical Rearrangements of o-Nitrobenzyl Compounds

Autor:	George Papageorgiou, Michael J. Gradwell, John E. T. Corrie
Rok vydání:	2010
Předmět:	chemistry.chemical_compound chemistry Ether General Medicine Cyanation Trifluoromethanesulfonate Medicinal chemistry Cyanohydrin
Zdroj:	ChemInform. 31
ISSN:	1522-2667 0931-7597
DOI:	10.1002/chin.200005056
Popis:	Three rearrangements of 2-nitrobenzyl compounds with increasingly complex structural changes are described. The first is a remarkably facile conversion of 2-nitrobenzyl triflate to 2-nitrosobenzaldehyde. The second is an unexpected formation of 1-acetyl-2,1-benzisoxazolone 7 during attempted preparation of the tert-butyl ester of O-acetyl 2-nitromandelic acid. The third, found in the reaction of 2-nitrobenzaldehyde cyanohydrin TMS ether 10 with cyclic secondary amines, results in oxidative cyanation of the position alpha to the amino group, giving the novel N-arylamino-α-cyanoamines 12a–e.
Databáze:	OpenAIRE
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