首页> 外文期刊>The Journal of Organic Chemistry >Novel Synthesis of 3,4-Diaminobutanenitriles and 4-Amino-2-butenenitriles from 2-(Cyanomethyl)aziridines through Intermediate Aziridinium Salts: An Experimental and Theoretical Approach
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Novel Synthesis of 3,4-Diaminobutanenitriles and 4-Amino-2-butenenitriles from 2-(Cyanomethyl)aziridines through Intermediate Aziridinium Salts: An Experimental and Theoretical Approach

机译:2-(氰基甲基)氮丙啶通过中间体氮丙啶鎓盐合成3,4-二氨基丁腈和4-氨基-2-丁腈的实验和理论方法

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摘要

1-Arylmethyl-2-(cyanomethyl)aziridines were transformed into 4-(N,N-bis(arylmethyl)ammo)-3-(pyrrolidin-1-yl)butanenitriles and 4-(N,N-bis(arylmethyl)amino)-2-butenenitriles via 4-(N,N-bis(arylmethyl)amino)-3-bromobutanenitriles in high yields and purity. The key steps involve the unprecedented regiospecific ring opening of intermediate 2-(cyanomethyl)aziridinium salts by bromide and pyrrolidine in acetonitrile, exclusively at the substituted aziridine carbon atom. The results were rationalized on the basis of ab initio calculations.
机译:将1-芳基甲基-2-(氰基甲基)氮丙啶转化为4-(N,N-双(芳基甲基)氨)-3-(吡咯烷-1-基)丁腈和4-(N,N-双(芳基甲基)氨基)-2-丁烯腈通过4-(N,N-双(芳基甲基)氨基)-3-溴丁腈腈以高收率和高纯度获得。关键步骤包括在溴腈和吡咯烷在乙腈中,仅在取代的氮丙啶碳原子上,中间体2-(氰基甲基)氮丙啶鎓盐的空位区域特异性开环。结果是从头算的基础上进行了合理化。

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