S-triazolo-1,5-benzodiazpine-4-ones

Details S-triazolo-1,5-benzodiazpine-4-ones S-triazolo-1,5-benzodiazpine-4-ones

1973-09-27

1978-02-21

Jiles, Henry R.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2602393B, 424244, 424269, C07D48704

Patent

active

040752020

ABSTRACT:
A s-triazolo-1,5-benzodiazepin-4-one selected from the group of compounds of the formulae: ##STR1## wherein R.sub.o is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive, hydroxy, hydroxymethyl, and ##STR2## in which R" and R'" are hydrogen or alkyl defined as above, or together ##STR3## is selected from the group consisting of pyrrolidino, piperidino, morpholino, and N-methylpiperazino; wherein R is hydrogen, alkyl of 1 to 3 carbon atoms, inclusive and ##STR4## in which R" and R'" are hydrogen or alkyl as defined above or together ##STR5## is defined as above; wherein R.sub.1 is hydrogen or methyl; wherein R.sub.2, R.sub.3, R.sub.4, and R.sub.5 are selected from the group consisting of hydrogen, alkyl alkyl defined as above, halogen, nitro, trifluoromethyl, and alkylthio in which alkyl is defined as above are produced from the corresponding 4-hydrazino-2H-1,5-benzodiazepines-2-ones of the formula (11A) ##STR6## wherein R.sub.1, R.sub.2, R.sub.3, R.sub.4, and R.sub.5 have the significance of above, with an acetic acid chloride or if R.sub.o is hydrogen with ethyl ortho-formate, and heating to an elevated temperature to give the corresponding 4H-s-triazolo[4,3-a][1,5]benzodiazepin-5(6H)-one which by additional procedures can be converted to the various compounds presented by formula 111A. Compounds of formula 111B are best obtained by reacting a 4-thio-1H-1,5-benzodiazepine-2,4-(3H,5H)-dione (1A) ##STR7## with a selected carbazate, followed by heating to an elevated level. Additional steps are necessary to synthesize the various compounds presented by formula 111B.

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