Premium
Synthesis of 4‐piperidazinethiols as potential antiradiation agents
Author(s) -
Kornet Milton J.,
Daniels Ralph
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170721
Subject(s) - chemistry , aluminum hydride , hydrolysis , hydrochloride , lithium (medication) , acid hydrolysis , organic chemistry , medicinal chemistry , catalysis , methoxide , endocrinology , medicine
The free radical addition of thioacetic acid to 1,2‐dicarbethoxy‐1,2,3,6‐tetrahydropyridazines gave high yields of 1,2‐dicarbethoxy‐4‐ S ‐thiolacetoxypiperidazines. The latter compounds served as the key intermediates in the preparation of 4‐piperidazinethiols. The thiolacetoxy derivatives were partially hydrolyzed to afford the related 1,2‐dicarbethoxy‐4‐piperidazinethiols. Complete hydrolysis of the thiolacetates gave rise to 4‐piperidazinethiols. Finally, lithium aluminum hydride reduction of the thiolacetoxy esters produced a series of 1,2‐dimethyl‐4‐piperidazinethiols. Only 4‐piperidazinethiol hydrochloride showed appreciable anti‐radiation activity.