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Purification free, chemoselective N-acylation of non-nucleophilic nitrogen heterocycles using oxyma and benzotriazole activations
Chemical Data Collections Pub Date : 2021-02-05 , DOI: 10.1016/j.cdc.2021.100654
Thoota Sandeep Kumar , Alice R. Robert , Himavathi Ganja , Pamerla Muralidhar , Kerru Nagaraju , Suresh Maddila

The chemoselective N-acylation of non-nucleophilic nitrogen heterocycles including indoles, pyrroles, pyrazole, and imidazole using ethyl 2-(tert-butoxycarbonyloxyimino)-2-cyanoacetate (Boc-Oxyma) under ambient conditions, which eludes purification and proceeds relatively fast with excellent yields, is reported. The substrate scope is broad, and the methodology is tolerant towards many other functional groups such as ester, aldehyde, nitro, iodo, bromo, cyano, and others. In addition to the methodology, the effect of base, solvent, temperature, and the mechanistic pathway is studied.



中文翻译:

使用氧化酶和苯并三唑的活化作用,对非亲核氮杂环进行无纯化的化学选择性N-酰化反应

在环境条件下使用2-(叔丁氧基羰基氧基亚氨基)-2-氰基乙酸乙酯(Boc-Oxyma)对非亲核氮杂环(包括吲哚,吡咯,吡唑和咪唑)进行化学选择性N-酰化,这使其难以纯化,并且在进行时相对较快地进行据报道,产量极高。底物范围广,并且该方法耐受许多其他官能团,例如酯,醛,硝基,碘,溴,氰基等。除了方法论之外,还研究了碱,溶剂,温度和机理途径的影响。

更新日期:2021-02-15
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