2007 Fused pyridine derivatives R 0450 Synthesis of 2,3-Dihydro-10bH-oxazolo[2,3-a]isoquinolines from ortho-Lithiated Phenyloxazolinyloxiranes. — Treatment of cis-configurated oxiranes of type (I) with organolithiums offers a new and simple method to prepare oxazoloisoquinoline derivatives. The reaction proceeds via formation of spirocyclic oxazolidine intermediates which can be trapped at low temperature. In contrast, trans-configurated analogues such as (V) behave differently. They do not form spirocyclic oxazolidines. Trapping of their lithiated derivatives with carbonyl compounds leads to dihydrobenzofurans like (VII). — (CAPRIATI, V.; FLORIO*, S.; LUISI, R.; PERNA, F. M.; J. Org. Chem. 72 (2007) 16, 6316-6319; Dip. Farmacochim., Univ. Bari, I-70125 Bari, Italy; Eng.) — Jannicke 51- 180

Synthesis of 2,3-Dihydro-10bH-oxazolo[2,3-a]isoquinolines from ortho-Lithiated Phenyloxazolinyloxiranes

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Page 1: Synthesis of 2,3-Dihydro-10bH-oxazolo[2,3-a]isoquinolines from ortho-Lithiated Phenyloxazolinyloxiranes

2007

Fused pyridine derivativesR 0450 Synthesis of 2,3-Dihydro-10bH-oxazolo[2,3-a]isoquinolines from ortho-Lithiated

Phenyloxazolinyloxiranes. — Treatment of cis-configurated oxiranes of type (I) with organolithiums offers a new and simple method to prepare oxazoloisoquinoline deriv-atives. The reaction proceeds via formation of spirocyclic oxazolidine intermediates which can be trapped at low temperature. In contrast, trans-configurated analogues such as (V) behave differently. They do not form spirocyclic oxazolidines. Trapping of their lithiated derivatives with carbonyl compounds leads to dihydrobenzofurans like (VII). — (CAPRIATI, V.; FLORIO*, S.; LUISI, R.; PERNA, F. M.; J. Org. Chem. 72 (2007) 16, 6316-6319; Dip. Farmacochim., Univ. Bari, I-70125 Bari, Italy; Eng.) — Jannicke

51- 180