Preparation and structure of pyrrolo[2,1-b]-and isoindolo[1,2-b][3,1]epoxyquinazolines

Various gamma-oxocarboxylic acids [aroylpropionic acids, cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid, diendo-3-benzoylbicyclo[2.2.1] heptane-2-carboxylic acid, formylbenzoic acid, methanobenzenecyclooctencarboxylic acid and the cyclopentadiene adduct of 3-trans-(4-methylbenzoyl)acrylic acid] were reacted with diexo-3-aminomethyl-7-oxabicyclo[2.2.1]hept-5-en-2-ylamine 2 to result in condensed pyrroloepoxyquinazolines 3-10. The starting 2 retained the diexo configuration, but cis -> trans isomerization took place when cis-2-(4-methylbenzoyl)cyclohexanecarboxylic acid was applied. The structures, including the ring annelations and the position of the aryl group on the new chiral centre, were established by means of NMR spectroscopy, and in the cases of the trans-3-(4-methylbenzoyl)acrylic acid-cyclopentadiene adduct for 10a, 10b and 10c by X-ray crystallography. (c) 2006 Elsevier B.V. All rights reserved.