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Ring closure reactions of diaminomaleonitrile (DAMN) with electrophilic aryl isocyanates and aryl isothiocyanates lead to the formation of the target 5,5′-diimino-1,1′-diaryl-4,4′-biimidazolidinylidene-2,2′-diones  2a,b  and 2,2′-diarylimino-4,4′-bithiazolidinylidenes  4a–e , respectively. The protocol provides a new strategy for the synthesis of a wide range of alkenes with two electron-donating and two withdrawing substituents of DAMN in moderate to good yields.

Diaminomaleonitrile as a versatile building block for the synthesis of 4,4′-biimidazolidinylidenes and 4,4′-bithiazolidinylidenes