An Efficient Synthesis of New 2-Pyronyl-1,5-Benzodiazepine Derivatives

Moktar Fodili; Mohamed Amari; Bellara Kolli; Albert Robert; Michèle Baudy-Floc'h; Philippe Le Grel

doi:10.1055/s-1999-3479

Synthesis 1999; 1999(5): 811-814
DOI: 10.1055/s-1999-3479

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An Efficient Synthesis of New 2-Pyronyl-1,5-Benzodiazepine Derivatives

Moktar Fodili^* , Mohamed Amari, Bellara Kolli, Albert Robert, Michèle Baudy-Floc'h, Philippe Le Grel

^*Groupe de Synthèse et Electrosynthèse Organiques, UMR CNRS 6510, Université de Rennes I, Campus de Beaulieu, F-35043 Rennes Cédex, France; Fax +33(2)99 28 67 38

Abstract

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A series of 3,4-dihydro-2-pyronyl-1,5-benzodiazepines 4 was prepared by the reaction of DHA (dehydroacetic acid), o-PDA (orthophenylenediamine) and aromatic aldehydes in the presence of a catalytic amount of TFA (trifluoroacetic acid). 2-Pyronyl-1,5-benzodiazepines 6 in turn were synthesised from DHA, o-PDA and acetal [dimethyl formamide-dimethyl acetal (DMF-DMA) or dimethyl acetamide-dimethyl acetal (DMA-DMA)] under basic catalysis.

dehydroacetic acid - orthophenylenediamine - aromatic aldehydes - acetal - pyronyl side chain - 1,5-benzodiazepines

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