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作为重要的双官能团化合物,合成新的邻溴代胺衍生物以及发展其新的合成方法具有重要意义,为此本研究建立了由β,β-二氰基苯乙烯衍生物、酰胺、N-溴代丁二酰亚胺(NBS)三组分一锅法合成相应邻溴代胺的新方法.在K2CO3催化下,β,β-二氰基苯乙烯衍生物与酰胺、NBS在二氯甲烷中、室温下反应(无需惰性气体保护),可高收率地得到邻溴代胺化合物(最高收率可达93%).考察了13种不同结构的β,β-二氰基苯乙烯衍生物与7种酰胺(丙烯酰胺、乙酰胺、戊酰胺、异丁酰胺、苯甲酰胺、对硝基苯甲酰胺、乌来糖)的反应,说明该方法不仅对β,β-二氰基苯乙烯具有广泛的适应性,也适用于不同类型的酰胺.所有产物结构均经核磁共振波谱、红外光谱及质谱确证,并提出了可能的反应机理.
As an important bifunctional compound, it is of great significance to synthesize new o-bromoamine derivatives and to develop new synthesis methods. To this end, it has been established that β, β-dicyanostyrene derivatives, amides, N- Bromosuccinimide (NBS) three-component one-pot synthesis of the corresponding o-bromoamine new method.Under K2CO3 catalysis, β, β-dicyanostyrene derivatives and amide, NBS in dichloromethane (Without the need of inert gas protection), the o-bromoamine compound can be obtained in high yield (the highest yield can reach 93%). Thirteen different structures of β, β-dicyanostyrene derived from The reaction of 7 kinds of amides (acrylamide, acetamide, valeramide, isobutyramide, benzamide, p-nitrobenzamide and raloid) shows that this method not only inhibits the formation of β, β-dicyanobenzene Ethylene has a wide range of adaptability, also applies to different types of amide.All product structures were confirmed by NMR, FTIR and mass spectrometry, and proposed a possible reaction mechanism.