Imines with rare α-heteroatom substituted amine components generated <i>in situ via</i> the Staudinger/aza-Wittig tandem reaction and their application in multicomponent reactions
作者:Polina Paramonova、Ilia Eliseev、Dmitry Dar'in、Olga Bakulina
DOI:10.1039/d3ob01832f
日期:——
for the in situ generation of imines via the Staudinger/aza-Wittig tandem reaction with aldehydes and triphenylphosphine. The obtained imines were successfully introduced into four types of multicomponent reactions: the Staudinger β-lactam synthesis with diazo carbonyl compounds, the Castagnoli–Cushman reaction with cyclic anhydrides, and the Ugi and azido-Ugi reactions with isocyanides and carboxylic
制备了一系列结构多样的 α-杂原子取代的甲基叠氮化物(XCH 2 N 3 ,其中 X = 邻苯二甲酰亚氨基、苯并三唑基、芳基硫基、芳氧基、烷氧基),并评估了通过Staudinger/aza-Wittig 串联原位生成亚胺的情况与醛和三苯基膦反应。所获得的亚胺被成功引入四种类型的多组分反应中:与重氮羰基化合物的Staudinger β-内酰胺合成、与环酸酐的Castagnoli-Cushman反应以及与异氰化物和羧酸或TMS-叠氮化物的Ugi和叠氮基-Ugi反应。这些转化使得能够制备具有复杂且先前难以接近的外围的四至七元内酰胺、无环双酰胺和5-(氨甲基)-1-烷基四唑。此外,已证明邻苯二甲酰亚胺衍生物可以脱保护以提供药用相关的N-氨基甲基内酰胺。