PREPARATION AND STERIC STRUCTURE ELUCIDATION OF PARTIALLY SATURATED ISOINDOLO[2,1-A][3,1]BENZOXAZINONES AND -[1,2-B][2,4]BENZOXAZEPINONES

摘要

The reactions of 2-carboxybenzaldehyde (1) with different 1,3- or 1,4-aminoalcohols (2a-i, 3a,b) were used to prepare partially saturated terra-and pentacyclic compounds containing a condensed 1,3-oxazino- or oxazepinoisoindolone moiety and one terminal saturated carbocycle. Isoindolo[2,1-a][3,1]benzoxazinones (4a-d, 6, 7), stereoisomeric isoindolo[1,2-b] [2,4] benzoxazepinones (5a-c) and pentacyclic derivatives (4e-g) were obtained. The diastereomers 5a-c differ in the ring annelation or in the positions of the NCHO hydrogens and annelational hydrogens. The stereostructures of these compounds were elucidated by means of H-1 and C-13 NMR spectroscopy, including DNOE, DEFT and 2D-HSC measurements. (C) 1997 Elsevier Science B.V. [References: 35]