Radical Rearrangement of Aryl/Alkylidene Malononitriles via Aza Michael Addition/Decynoformylation/Addition Sequence: An Access to α-Aminonitriles and α-Aminoamides,The Journal of Organic Chemistry

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Radical Rearrangement of Aryl/Alkylidene Malononitriles via Aza Michael Addition/Decynoformylation/Addition Sequence: An Access to α-Aminonitriles and α-Aminoamides
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2020-11-04 , DOI: 10.1021/acs.joc.0c01358
Shubhangi P. Bhoite _{1,

2} , Ajay H. Bansode _{1,

2} , Gurunath Suryavanshi _{1,

2}

Affiliation

An efficient, safe, and environmentally friendly tertiary butyl hydrogen peroxide (TBHP)-mediated rearrangement of aryl/alkylidene malononitrile with anilines has been developed with in situ generation of HCN as the cyanide source for the synthesis of substituted α-aminonitriles and α-aminoamide. A diverse set of α-aminonitriles and α-aminoamides was efficiently synthesized in good to excellent yields. This method features a broad substrate scope and good functional group tolerance, and the in situ-generated HCN bypasses the use of an external cyanide source.

中文翻译：

通过Aza Michael加成/癸基甲酰化/加成序列对芳基/亚烷基丙二腈进行自由基重排：获得α-氨基腈和α-氨基酰胺

已经开发出一种高效，安全，环保的叔丁基过氧化氢（TBHP）介导的芳基/亚烷基丙二腈与苯胺的重排反应，并原位生成HCN作为氰化物来源，用于合成取代的α-氨基腈和α-氨基酰胺。有效地合成了多种多样的α-氨基腈和α-氨基酰胺，收率很高。该方法具有广泛的底物范围和良好的官能团耐受性，并且原位生成的HCN无需使用外部氰化物源。

更新日期：2020-12-04

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