1,2,3-TRIAZOLODIAZEPINES .1. PREPARATION AND BENZODIAZEPINE RECEPTOR-BINDING OF 1-BENZYL-1,2,3-TRIAZOLO-[4,5-B][1,4]DIAZEPINES AND 1-PHENETHYL-1,2,3-TRIAZOLO-[4,5-B][1,4]DIAZEPINES

Several new 1,2,3-triazolo[4,5-b][1,4]diazepines were prepared startin g from 1-benzyl-1 and 1-phenethyl-4,5-diamino-1,2,3-triazole 2 (Scheme 1), by condensation reactions with beta-diketones (Scheme 2), beta-ke toesters (Scheme 3), and diethyl malonates (Scheme 4). In the first ca se we obtained compounds 3 and 4 with basic properties, while the este r function condensations gave cyclic amide derivatives 7, 8, 10, 12 an d 13 with acid properties. Some N-methyl derivatives 11, 14 and 15 wer e obtained from the cyclic amide compounds. Most of compounds were tes ted for their ability to displace [H-3]flunitrazepam from bovine brain membranes but no compound showed benzodiazepine receptor binding affi nity.