Synthesis of <i>α</i>-Aryl Nitriles via Nucleophilic Substitution of <i>α</i>-Cyanohydrin Methanesulfonates with Malonates

Wang, Leigang; Zheng, Yanfang; Zhou, Xi; Wang, Haifeng; Yan, Qiongjiao; Wang, Wei; Chen, Fen‐Er

doi:10.6023/cjoc202208029

Chinese Journal of Organic Chemistry

2023

DOI: 10.6023/cjoc202208029

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Synthesis of α-Aryl Nitriles via Nucleophilic Substitution of α-Cyanohydrin Methanesulfonates with Malonates

Leigang Wang¹,

Yanfang Zheng²,

Xi Zhou³

et al.

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2024

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Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles

Zhang,

Tian,

Huang

et al. 2024

Chinese Journal of Organic Chemistry

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An efficient synthesis of α-aminonitriles via nucleophilic substitution of α-cyanohydrin methanesulfonates with aromatic amines was developed. This transition metal-free protocol has the advantages of cheap and easily available starting materials, broad substrate scope, excellent functional group compatibility, and very mild and simple operations. Furthermore, this strategy could also be applicable to quaternary α-cyanohydrin methanesulfonates and various nitrogen nucleophiles. A range of derivatives were readily obtained through subsequent elaboration of α-aminonitriles. Keywords α-aminonitrle; α-cyanohydrin methanesulfonate; aromatic amine; nucleophilic substitution α-氨基腈是一类同一碳原子含氨基和氰基双官能团的化合物, 由于氨基和氰基在合成化学中扮演着重要角色, 易于发生各种官能团转化, 使得 α-氨基腈类化合物逐渐成为各种重要有机化合物(如 α-氨基酸、α-氨基醛、α-氨基醇、1,2-二胺和多种含氮杂环化合物(吲哚、吡咯、咪唑和噻二唑等)的关键前体 [1] . 此外, 氨基和氰基官能团都是非常重要的药效基团, 氨基能充当氢键供体和受体并参与静电相互作用; 氰基由于较强的吸电子性质使其成为良好的氢键受体, 且体积较小使其能快速接近靶标蛋白参与氢键作用和 π-π 相互作用. 因此, 许多天然产物、已知药物和潜在的候选药物都含有 α-氨基腈这类结构片段, 如图 1 所示的天然产物 Sarframycin A [2] 、Phthalascitin 650 [3] 和 Girgensohnine [4] , 它们分别从淡紫色链霉菌、海洋被囊动物以及沙漠植物 Gensohnia oppositiflora 中提取, 在抗肿瘤和杀虫活性方面有很好功效. 近年来, 越来越多含 α-氨基腈结构的药物分子被开发出来, 如在临床上用于治疗骨质疏松症的组织蛋白酶 K 抑制剂 Odanacatib [5] , 它具有强力的药效且易于在体内代谢; 用于治疗Ⅱ型糖尿病的可逆型二肽激酶抑制剂 Saxagliptin [6] 和 Vildagliptin [7] , 两者结构虽然非常相似, 但药效却有很大差别. 基于 α-氨基腈类化合物重要的生物药理活性和应用价值, 对其合成方法的研究逐渐成为合成领域研究热点.

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Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles

Zhang,

Tian,

Huang

et al. 2024

Chinese Journal of Organic Chemistry

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Synthesis of α-Aryl Nitriles via Nucleophilic Substitution of α-Cyanohydrin Methanesulfonates with Malonates

Cited by 1 publication

References 43 publications

Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles

Application of α-Cyanohydrin Methanesulfonates for the Synthesis of α-Aminonitriles

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