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.
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 65174, Iran. rgvaghei@yahoo.com.
Ramin
R
Ghorbani-Vaghei
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 65174, Iran.
Yaser
Y
Maghbooli
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 65174, Iran.
Azadeh
A
Shahriari
Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 65174, Iran.
Jafar
J
Mahmoodi
D001463:Barbiturates / Q000138:chemical synthesis* / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D003521:Cyclopropanes / Q000737:chemistry*; D015394:Molecular Structure; D013141:Spiro Compounds / Q000737:chemistry*; D013449:Sulfonamides / Q000737:chemistry*
D001463:Barbiturates; D003521:Cyclopropanes; D013141:Spiro Compounds; D013449:Sulfonamides
Carbonyl compounds; Intramolecular ring-closing reaction; N-Halosulfonamides; Spirocyclopropane; Spirocyclopropylbarbiturate