We designed organoselenium analogs of pyridazine in which an allylselenium moiety was introduced at the 3-position of the pyridazine nucleus and the 6-position was substituted with an oxygen and sulfur atom. Novel 3-allylseleno-6-alkoxy(or alkylthio)pyridazines were prepared through the alkoxylation (or alkylthiolation) of 3-allylseleno-6-chloropyridazine and the related alcohol (or thiol) in order to discover potential antitumor candidates. Elemental selenium suspended in dimethylformamide reacts with hydrazine hydrate at rt to give dark green solution containing diselenide anion. The diselenide anion thus formed reacts in situ with the 3,6-dichlorpyridazine. The dichloropyridazinyl diselenide can be reduced to 3-chloropyridazinyl selenolate anion using hydrazine hydrate at rt. The anion thus formed reacts with allyl bromide to give the 3-allylseleno-6-chloropyridazine. The final 3-allylselenopyridazines were prepared from 3-allylseleno-6-chloropyridazine with a various nuclephillic agent. We searched another synthetic method to improve low yields. Another synthetic route for the targets was proceeded via alkylthiolation, deselenylation, hydrolysis and allylation from dichloropyridazine.

New organoseleniums for anticancer agents: Synthesis of alkylselenopyridazine derivatives via allyic alkylation of diselenides

245th National Meeting (2013)

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