Journal of the Chemical Society. Perkin transactions I p. 360 - 365 (1981)
Update date:2022-07-30
Topics:
Askari, Syed H.
Moss, Stephen F.
Taylor, David R.
1-Chloro-1,4-diaryldiazabutadienes (1) react with thiourea to give hydrochlorides of 4-amidino-2,5-diaryl-Δ2-1,3,4-thiadiazolines from which the corresponding free bases (2) are obtained by treatment with cold alkali.Imidazolidine-2-thione (ethylenethiourea) reacts similarly with the chlorodiazabutadienes (1a,b) to give, after treatment with cold alkali, 4-(4,5-dihydroimidazolin-2-yl)-2,5-diaryl-Δ2-1,3,4-thiadiazolines (6a,b).In the presence of an excess of sodium borohydride the reaction of (1a) with thiourea yielded some N2-benzylthiobenzoylhydrazine (12), compatible with the capture of an intermediate iminium ion.A mechanism is suggested for these reactions.
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