Synthesis of Spiro-lactams and Polysubstituted Pyrroles via Ceric Ammonium Nitrate-Mediated Oxidative Cyclization of N-Furan-2-ylmethyl-ß-Enaminones.
J Org Chem
; 81(12): 4939-46, 2016 06 17.
Article
em En
| MEDLINE
| ID: mdl-27206153
ABSTRACT
Spiro-lactams and polysubstituted pyrroles were synthesized by reactions of furfurylamines with ynones followed by oxidation. Specifically, the protocol involved in situ generation of N-furan-2-ylmethyl-ß-enaminones and their subsequent oxidation by ceric ammonium nitrate (6 equiv for spiro-lactam formation, 3 equiv for pyrrole formation). This useful dearomatizing oxidation, which likely proceeds via a free-radical pathway, can be expected to extend the synthetic applications of furan and pyrrole derivatives.
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Base de dados:
MEDLINE
Idioma:
En
Revista:
J Org Chem
Ano de publicação:
2016
Tipo de documento:
Article