Domino synthesis of 5-aminoimidazoles from Strecker multicomponent adducts via ytterbium-promoted isocyanide insertion/5-exo-dig cyclization

被引：2

作者：

Cannalire, Rolando ^{[1
]}

Russo, Camilla ^{[1
]}

Luciano, Paolo ^{[1
]}

Cerra, Bruno ^{[2
]}

Gioiello, Antimo ^{[2
]}

Brunelli, Francesca ^{[3
]}

Tron, Gian Cesare ^{[3
]}

Giustiniano, Mariateresa ^{[1
]}

机构：

[1] Univ Naples Federico II, Dept Pharm, Via Montesano 49, I-80131 Naples, Italy

[2] Univ Perugia, Dept Pharmaceut Sci, Lab Med & Adv Synthet Chem Lab MASC, Via Liceo 1, I-06123 Perugia, Italy

[3] Univ Piemonte Orientale, Dept Drug Sci, Largo Donegani 2, I-28100 Novara, Italy

来源：

MOLECULAR DIVERSITY | 2023年 / 27卷 / 01期

关键词：

Isocyanides; Domino reactions; Multicomponent reactions; Lewis acid catalysis; 5-Aminoimidazoles; ISONITRILES; PROPARGYLAMINES; POLYMERIZATION; IMIDAZOLES;

D O I：

10.1007/s11030-022-10418-4

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

A new Lewis acid promoted domino isocyanide insertion/5-exo-dig cyclization of readily available Strecker 3-component adducts to 4-substituted 5-aminoimidazole derivatives is herein reported. Despite their potential as relevant heterocyclic scaffolds in medicinal chemistry programs, this class of compounds is still underrepresented, with current synthetic strategies poorly efficient in terms of timing and yields. To this end, we show how the exploitation of unconventional reactivities of isocyanides, promoted by ytterbium-triflate, could represent a key resource to enable a fast and easy access to such an unexplored area of the chemical space.

引用

页码：511 / 515

页数：5

共 23 条

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