Hydroxyalkyl substituted triazolidin-3-ones (3, Y = O) and -3-thiones (3, Y = S) were synthesized employing either a one pot procedure using the ketone (1) or a stepwise reaction sequence starting from the a-hydroxyphenylhydrazones (2). In the case of benzoin phenylhydrazone an interesting AZOALKENE TYPE REACTION occured, leading to the imidazolinethione rather than to the triazolidine-3-thione. |
In these compounds the hydroxy group can be easily ACYLATED. Both the triazolidin-3-ones and -3-thiones (3, Y = O/S) could be acetylated and benzoylated using appropriate methods. In the case of triazolidin-3-ones (3, Y = O) the hydroxy group could also be TOSYLATED. When treated with base the tosylated heterocyclic systems underwent an interesting RING ENLARGEMENT REACTION.
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