Facile and efficient approach for the synthesis of spirocyclopropylbarbiturates and 3-substituted-1,1,2,2-tetracyanocyclopropanes using N-halosulfonamides
| Autor: | Azadeh Shahriari, Jafar Mahmoodi, Ramin Ghorbani-Vaghei, Yaser Maghbooli |
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| Rok vydání: | 2016 |
| Předmět: |
Cyclopropanes
010402 general chemistry 01 natural sciences Medicinal chemistry Catalysis Domino Prime (order theory) Inorganic Chemistry chemistry.chemical_compound Drug Discovery Organic chemistry Combinatorial Chemistry Techniques Spiro Compounds Physical and Theoretical Chemistry Molecular Biology Malononitrile Sulfonamides Molecular Structure 010405 organic chemistry Chemistry Organic Chemistry Halogenation General Medicine 0104 chemical sciences Intramolecular force Reagent Barbiturates Michael reaction Information Systems |
| Zdroj: | Molecular diversity. 20(4) |
| ISSN: | 1573-501X |
| Popis: | The applications of $$N{,}N{,}N^{\prime }{,}N^{\prime }$$ -tetrabromobenzene-1,3-disulfonamide [TBBDA], poly(N-bromo-N-ethyl-benzene-1,3-disulfonamide) [PBBS], $$N{,}N{,}N^\prime {,}N^\prime $$ -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 |
| Databáze: | OpenAIRE |
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