New heterocyclic skeletons derived from the aporphine alkaloid boldine

Sobarzo-Sanchez, E; Jullian C.; CASSELS, BK; Saitz C.

Abstract

The abundant aporphine alkaloid (S)-(+)-boldine (1) was selectively nitrosated with sodium nitrite in acetic acid affording 8-nitrosoboldine (2) which was hydrogenated catalytically to give 8-aminoboldine (3). The latter was used as the starting material for annulations with ethyl ortho-formate to afford the corresponding oxazole ("boldine-9,8-oxazole", 4), and with methyl benzoylformate giving the phenyl-oxazinone ("boldine-9,8-phenyloxazinone", 5). This later product was treated with KOH/EtOH at room temperature and converted quickly into the ring-contracted phenyloxazole ("boldine-9,8-phenyloxazole", 6) in moderate yield.

Más información

Título según WOS: New heterocyclic skeletons derived from the aporphine alkaloid boldine
Título según SCOPUS: New heterocyclic skeletons derived from the aporphine alkaloid boldine
Título de la Revista: SYNTHETIC COMMUNICATIONS
Volumen: 32
Número: 23
Editorial: TAYLOR & FRANCIS INC
Fecha de publicación: 2002
Página de inicio: 3687
Página final: 3693
Idioma: English
URL: http://www.tandfonline.com/doi/abs/10.1081/SCC-120014990
DOI:

10.1081/SCC-120014990

Notas: ISI, SCOPUS