New Synthesis of 1,4 Benzodiazepine-2,5-diones by Means of HCL Gas Catalyst
作者:M. Akssira、M. Boumzebra、H. Kasmi、A. Dahdouh、M. L. Roumestant、Ph. Viallefont
DOI:10.1080/00397919308013783
日期:1993.8
Abstract A new synthesis of 1,4- benzodiazepinediones 4 , particularly 1,4-dihydro1H-1,4-benzodiazepine-2,5-dione, 4c key intermediate of metabolites cyclopenin 9 , cyclopenol 10 , cyclopeptine 11 and dehydrocyclopeptine 12 , was achieved by action of dry HCl gas in DMF on compound 3 prepared from anthranilic acid derivative 1 and amino ester 2 .
synthetic pathway was applied in solid phase, from commercially available anthranilic acid that was bound to hydroxymethyl polystyrene resin via a carbamate linker. In both cases, cyclisation occurred underbasicconditions to afford non-racemized quinazolinediones in high purity.
1,4-benzodiazepin-2,5-diones have been synthesized in good overall yields by two routes, the first one by cyclisation of dipeptides prepared from Boc anthranilic acid and alpha-amino acid methyl esters, the second one by reaction of N-carboxy alpha-amino acid anhydrides with Boc anthranilic acid.
FEIGEL, MARTIN;LUGERT, GERHARD, LIEBIGS ANN. CHEM.,(1989) N1, C. 1089-1092