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

✍ Scribed by Iván Kanizsai; Ferenc Miklós; Pál Sohár; Antal Csámpai; Reijo Sillanpää; Géza Stájer

Publisher: Elsevier Science
Year: 2007
Tongue: English
Weight: 400 KB
Volume: 831
Category: Article
ISSN: 0022-2860
DOI: 10.1016/j.molstruc.2006.07.019

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✦ Synopsis

Various -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 conWguration, 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.

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