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64349116547
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-subsituted C=N double bond via domino isomerization of a gem-dichloroaziridine-intramolecular Friedel-Crafts acylation of the O-tethered benzene ring and subsequent intramolecular cyclization induced by hydride, was realized for 1-aryl-1, 11b-dihydroazirino[1, 2-d]dibenz[b, f][1, 4]oxazepines. The latter are excellent precursors of azomethine ylides, especially in solvent-free conditions, which can undergo a completely stereoselective 1, 3-dipolar cycloaddition to C=C dipolarophiles giving derivatives of dibenzo[b, f]pyrrolo[1, 2-d][1, 4]oxazepine. © 2009 American Chemical Society 10.1021/ol802813a CCC: 40.75
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(arylchloromethyl) -subsituted C=N double bond via domino isomerization of a gem-dichloroaziridine-intramolecular Friedel-Crafts acylation of the O-tethered benzene ring and subsequent intramolecular cyclization induced by hydride, was realized for 1-aryl-1, 11b-dihydroazirino[1, 2-d]dibenz[b, f][1, 4]oxazepines. The latter are excellent precursors of azomethine ylides, especially in solvent-free conditions, which can undergo a completely stereoselective 1, 3-dipolar cycloaddition to C=C dipolarophiles giving derivatives of dibenzo[b, f]pyrrolo[1, 2-d][1, 4]oxazepine. © 2009 American Chemical Society 10.1021/ol802813a CCC: 40.75
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