The addition of N-protected O-sulfonyl hydroxylamine derivatives on 2-alkylidene 3-oxo nitrites gives 2,5-disubstituted 4-cyano 2,3-dihydrooxazoles (4-oxazolines) by a practical and efficient synthetic procedure under very mild conditions in high yields. Likely. the formation of N,O-heterocycles proceeds through a domino reaction involving a fast rearrangement of unstable 2-acyl 2-cyano aziridines.
Efficient synthesis of 4-cyano 2,3-dihydrooxazoles by direct amination of 2-alkylidene 3-oxo nitriles / E., Burini; Fioravanti, Stefania; Morreale, Alberto; Pellacani, Lucio; Tardella, Paolo Antonio. - In: SYNLETT. - ISSN 0936-5214. - STAMPA. - (2005), pp. 2673-2675. [10.1055/s-2005-917097]
Efficient synthesis of 4-cyano 2,3-dihydrooxazoles by direct amination of 2-alkylidene 3-oxo nitriles
FIORAVANTI, Stefania;MORREALE, Alberto;PELLACANI, Lucio;TARDELLA, Paolo Antonio
2005
Abstract
The addition of N-protected O-sulfonyl hydroxylamine derivatives on 2-alkylidene 3-oxo nitrites gives 2,5-disubstituted 4-cyano 2,3-dihydrooxazoles (4-oxazolines) by a practical and efficient synthetic procedure under very mild conditions in high yields. Likely. the formation of N,O-heterocycles proceeds through a domino reaction involving a fast rearrangement of unstable 2-acyl 2-cyano aziridines.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
