Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides.

The applications of [Formula: see text]-tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], [Formula: see text]-tetrachlorobenzene-1,3-disulfonamide [TCBDA], and poly(N-chloro-N-ethyl-benzene-1,3-disulfonamide) [PCBS] as novel reagents for the preparation of spirocyclopropylbarbiturates from 2-arylidenemalononitriles and barbituric acids are described. In addition, an effective and simple domino procedure for the synthesis of 3-substituted-1,1,2,2-tetracyanocyclopropanes from carbonyl compounds and malononitrile in a one-pot manner is reported. These reactions involve Michael addition, halogenation, and intramolecular ring-closing (MHIRC) reaction sequences. We have developed an efficient procedure for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using TBBDA, PBBS, TCBDA, and PCBS as new reagents.