Details

Autor(en) / Beteiligte

• Anitha, Mandala
• Gangadhararao, G
• Kumara Swamy, K. C

Titel

Base catalysed intermolecular cyclisation of N-protected o-amino benzaldehyde/acetophenone with phosphorus/sulphur based allenes: facile synthesis of substituted quinolinesElectronic supplementary information (ESI) available: Experimental details, copies of 1H/13C NMR spectra and CIF data. CCDC 1447739-1447745. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c6ob00259e

Erscheinungsjahr

2016-03

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• Reaction of N -Bz protected o -aminobenzaldehyde or acetophenone with allenylphosphonates in the presence of a simple base leads to quaternary carbon substituted phosphono-quinolines which undergo thermal rearrangement to O -phosphorylated quinolines. The present one-pot reaction involves intermolecular cyclisation, dehydration, and benzoyl group rearrangement followed by a novel phosphoryl group migration. The migration was less facile/not observed in the reactions using allenylphosphine oxides and sulphur based allenes wherein only substituted quinolines were obtained in good yields. X-ray structures have been determined for the key products. Base catalyzed reaction of N -Bz protected o -aminobenzaldehyde with allenylphosphonates affords O -phosphorylated quinolines via a route involving a thermal rearrangement.