Abstract
Novel tricyclic substituted 5,6-dihydro-4H-[1,2,4]oxadiazolo[4,3-a][1,5]benzodiazepin-1-one derivatives were prepared by the thermal intramolecular cyclization of tetrahydro-1,5benzodiazepin-2-one O-(ethoxycarbonyl)oximes. The latter were obtained from the corresponding hydroxyimino-1,5-benzodiazepines and ethyl chloroformate.
Highlights
The ability of the benzodiazepines as a chemical class to have an effect on different processes in the organism has found application as pharmaceutical.1 It is known, that the pharmaceutical activity appears to be exchanged when different heterocyclic rings are annelated to the basic 1,4-and 1,5-benzodiazepine systems.1,2 In previous papers we have reported the synthesis of polycyclic peri-annelated imidazo[1,5]benzodiazepines3 and derivatives containing imidazo4, triazolo5 and thiazolo6 nucleus fused to the “a” edge of the seven-membered ring of the 1,5-benzodiazepine system
Thiolactams 1a-i were synthesized to supplement the lack of reactivity of the corresponding lactams6,12 towards nucleophiles
Thiolactams 1a-i were converted to the hydroxyimino-1,5-benzodiazepines 2a-i in good yields by the action of hydroxylamine hydrochloride in boiling dry ethanol in the presence of sodium acetate (Scheme 1)
Summary
The ability of the benzodiazepines as a chemical class to have an effect on different processes in the organism has found application as pharmaceutical. It is known, that the pharmaceutical activity appears to be exchanged when different heterocyclic rings are annelated to the basic 1,4-and 1,5-benzodiazepine systems. In previous papers we have reported the synthesis of polycyclic peri-annelated imidazo[1,5]benzodiazepines and derivatives containing imidazo, triazolo and thiazolo nucleus fused to the “a” edge of the seven-membered ring of the 1,5-benzodiazepine system. The ability of the benzodiazepines as a chemical class to have an effect on different processes in the organism has found application as pharmaceutical.. The ability of the benzodiazepines as a chemical class to have an effect on different processes in the organism has found application as pharmaceutical.1 It is known, that the pharmaceutical activity appears to be exchanged when different heterocyclic rings are annelated to the basic 1,4-and 1,5-benzodiazepine systems.. In continuation of our investigation on tricyclic benzodiazepines, we have extended the cycloaddition strategy to develop a synthetic pathway towards 1,5benzodiazepines including a 1,2,4-oxadiazole nucleus. Compounds incorporating different oxadiazole rings have been attracting widespread attention due to their broad spectrum of biological activity in both agrochemical and pharmaceutical fields.. Some [1,2,4]oxadiazolo[1,5]benzodiazepine derivatives were prepared via the 1,3-dipolar cycloaddition to the dipolarophile C=N moiety of the diazepine skeleton.
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