Preparation and structure of pyrrolo- and isoindoloquinazolinones

Aroylpropionic acids react with cis- and trans-2-aminocyclohexane- or 4-cyclohexene-1-carboxamides and diexo-norbornane/ene analogues to give saturated or partly saturated pyrroloquinazolinones and methylene-bridged derivatives. In the reactions of 2-formylbenzoic acid or 2-aroylbenzoic acid with aminocarboxamides, the isoindoloquinazolinones were formed. Bisacyl derivatives were also isolated. The product aminocarboxamides always retained their starting cis, trans, diexo or diendo configurations. The structures, including the ring annelations and the position of the aryl group or, for the reaction of formylbenzoic acid, that of the H atom on the new chiral centre, were established by means of NMR spectroscopy. q 2004 Elsevier B.V. All rights reserved.