期刊
TETRAHEDRON
卷 60, 期 48, 页码 11029-11039出版社
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2004.07.107
关键词
isoindole; imidazole; benzimidazole; [1,4]diazepine; N-acyliminium ion; alpha-aza-amidoalkylation; kinetic versus thermodynamic control
Efficient assembly of substituted imidazo[2,1-a]isoindolones I is reported from suitable alpha,beta-diamine IV (or corresponding (beta-nitroamine) and phthalic anhydride (1) in a three- or four-step sequence in good yields. The key step of this methodology is based on an intramolecular alpha-aza-amidoalkylation of the N-acyliminium species. Furthermore, when R-2 is an aromatic moiety a competing alpha-amidoalkylation took place and imidazo[2,1-a]isoindolones (or benzimidazo[2,1-a]isoindolones) I and/or isoindolo[1,4]benzodiazepines III were obtained under kinetic or thermodynamic control. The chemoselectivity of these transformations is also discussed. (C) 2004 Elsevier Ltd. All rights reserved.
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