[Reaction between 2-nitrobenzoylaminomalonate and acrylic aldehyde for the synthesis of compounds with the pyrrolo/2,1-ch h 1,4/benzodiazepine structure].
The synthesis of 5,11-dioxo-1,2,3,10,11,11a-hexahydro-5H-pyrrolo (2,1-c) (1,4)benzodiazepine and 2-bromo-5,11-dioxo-1,10,11,11a-tetrahydro-5H-pyrrolo (2,1-c) (1,4)benzodiazepin-11a-ethylcarboxylate, structurally related to anthramycin and tomaymycin, was achieved by forming in situ the pyrrolidine nucleus instead of using proline or its derivatives. The most important intermediate was 1-(2-nitrobenzoyl)-delta4-pyrrolin-2,2-dicarboxylate which was then easily transformed into the above-mentioned tricyclic systems, starting with catalytic reduction or bromination.
D000179:Acrylates; D001569:Benzodiazepines / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D008314:Malonates; D009578:Nitrobenzenes; D011759:Pyrrolidines / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared
D000179:Acrylates; D007202:Indicators and Reagents; D008314:Malonates; D009578:Nitrobenzenes; D011759:Pyrrolidines; D001569:Benzodiazepines
La reazione tra 2-nitrobenzoilaminomalonato ed aldeide acrilica per la sintesi di composti a struttura pirrolo (2,1-c) (1,4) benzodiazepinica