Synthesis of Fused Diaziridine Derivatives from Cyclic Secondary Amines by Utilizing N-Bromosulfonamides as an Aminating Reagent
Synthesis of Fused Diaziridine Derivatives from Cyclic Secondary Amines by Utilizing N-Bromosulfonamides as an Aminating Reagent
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DOI：
10.1055/a-1468-8275
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发表时间：
2021-03-29
影响因子：
2.6
通讯作者：
Minakata，Satoshi
中科院分区：
文献类型：
--
作者：
Kiyosu，Yuuki;Tanaka，Shino;Minakata，Satoshi
在N-溴代丁二酰亚胺(NBS)和合适的碱存在下，通过环仲胺与对甲苯磺酰胺反应，合成了一系列现有方法难以获得的稠合二氮杂环丙烷。这一氧化体系能够有效地在原位形成关键中间体，即溴胺(环亚胺的前体)和N-溴磺酰胺。此外，还报道了以N-溴-N-钠-对甲苯磺酰胺(溴胺-T)为原料，在少量CF3CO2H催化下合成稠合二氮杂环丙烷的另一种方法。
The synthesis of a series of fused diaziridines, which are difficult to access by existing methods, was achieved by the reaction of cyclic secondary amines withp-toluenesulfonamide in the presence ofN-bromosuccinimide (NBS) and a suitable base. This oxidation system enables the efficient in situ formation of the key intermediates, which areN-bromoamines (a precursor of cyclic imines) andN-bromosulfonamides. In addition, an alternative method usingN-bromo-N-sodio-p-toluenesulfonamide (bromamine-T) in the presence of a catalytic amount of CF3CO2H for the synthesis of fused diaziridines is also reported.