Intermediates and process for the production of certain triazolo

Details Intermediates and process for the production of certain triazolo Intermediates and process for the production of certain triazolo

1974-06-19

1976-03-30

Narcavage, Joseph A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424269, C07D24908

Patent

active

039474666

ABSTRACT:
A multi-step process for the preparation of 1-[(amino - or substituted amino)methyl]-6-phenyl-4H-s-triazolo-[4,3-a][1,4]benzodiazepines of the formula VI: ##SPC1##
wherein R' is hydrogen or alkyl of 1 to 3 carbon atoms, inclusive, and wherein the rings A and B are unsubstituted or substituted by one or two substituents selected from the group consisting of chloro, fluoro, bromo, nitro, and trifluoromethyl, which comprises: treating a compound of the formula I: ##SPC2##
wherein rings A and B are defined as above, with acetic anhydride and formic acid to obtain compound II: ##SPC3##
wherein A and B rings have the significance as above, treating compound II with sufficient formaldehyde to produce compound III, the 3,5-bis(hydroxymethyl)derivative of II; treating III with phthalimide, triphenylphosphine and diethyl azodicarboxylate to give compound IV, the 3,5-bis(phthalimidomethyl) derivative of II; and treating IV with hydrazine hydrate to obtain a compound of formula V ##SPC4##
wherein rings A and B are defined, as herein above. Compound V can then be alkylated in known manner to give those compounds of formula VIa which corresponds to formula VI when R' is desired to be alkyl.
The compounds of formula VI have antidepressant and antianxiety effects in mammals and birds.

REFERENCES:
allgeier et al., Chem. Abstracts, 77:126711r (1972).
Okamoto et al., Chem. Abstracts, 77:126709w (1972).

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