RESUMO
A novel strategy via the triple process (multicomponent reactions (MCR)-domino)/tandem was developed for the synthesis of restricted and constrained bis-1,2,3-triazole-linked pyrrolo[3,4-b]pyridine peptidomimetics dimers in overall yields of 20-55%. This strategy allows the construction of six heterocycles in two stages of the reaction.
Assuntos
Química Click/métodos , Reação de Cicloadição/métodos , Dimerização , Peptidomiméticos/síntese química , Cromatografia em Camada Fina , Cianetos/química , Espectroscopia de Ressonância Magnética , Espectrometria de Massas , Estrutura Molecular , Piridinas , Espectrometria de Massas por Ionização por Electrospray , Especificidade por Substrato , TriazóisRESUMO
Isocyanide-based multicomponent reactions are a versatile tool in the synthesis of heterocycles. This review describes recently developed approaches based on the combination of consecutive or repetitive isocyanide-based multicomponent reactions for the synthesis of structurally diverse heterocycles. These strategies have also allowed the synthesis of a plethora of macroheterocycles in a reduced number of steps.
RESUMO
Isocyanide-based multicomponent reactions (IMCRs) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles. Our strategy was accomplished in only three steps: first, a one-pot hydrazino-Ugi-azide four-component reaction; second a hydrazinolysis and finally an additional hydrazino-Ugi-azide reaction. This sequence provides the title compounds in moderate to excellent yields. The products synthesized herein contain functional groups within their structures that can be easily modified to obtain new acylhydrazino 1,5-disubstituted tetrazoles.