IQUIR 05412
INSTITUTO DE QUIMICA ROSARIO
Unidad Ejecutora - UE
artículos
Título:
A straightforward synthesis of 5-methylaaptamine from eugenol, employing a 6π-electrocyclization reaction of a 1-azatriene
Autor/es:
DANIEL A. HEREDIA; TEODORO S. KAUFMAN; ENRIQUE L. LARGHI
Revista:
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Editorial:
WILEY-V C H VERLAG GMBH
Referencias:
Lugar: Weinheim; Año: 2016 p. 1397 - 1404
ISSN:
1434-193X
Resumen:
5-Methylaaptamine, an analog of the naturally-occurring aaptamine, was synthesized from eugenol, employing an A->AC->AC-B ring system constructive strategy. The synthetic sequence entailed building a 2,3-dihydro-1H-quinolin-4-one through an aza-Michael/sulfonamidation/Friedel-Crafts cyclization, whilst the 6phi-electro cyclization of a 1-azatriene was the final key step served to construct the remaining C-ring.
