Abstract
Ethenetetracarbonitrile (2, in tetrahydrofuran solution), diethyl (E)-2,3-dicyanobutenedioate (10, in tetrahydrofuran solution), and 7,7′,8,8′-tetracyanoquinodimethane (16, in pyridine solution) act on 1-substituted-2,5-dithiobiureas 1a–c, forming the derivatives of imidazothiadiazole 5a–c, thiadiazine 11a–c and 12a–c, spiro(thiadiazolopyrimidinocyclohexadiene)malononitrile 17a–c and diazospiroundecatetraene 18a–c. Rationales for these conversions involving the nucleophilic addition on diycanomethylene carbon atom are presented.
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