RESUMO
A synthetic strategy to fused bicyclic piperidines-building blocks for medicinal chemistry-is developed. The key step was an intramolecular [2 + 2]-photocyclization. The photochemical step was performed on a gram scale. Crystallographic analysis of the obtained compounds revealed that they occupy a novel chemical space and can be considered as elongated analogues of 3-substituted piperidines.
Assuntos
Química Farmacêutica , Piperidinas , EstereoisomerismoRESUMO
Synthesis of the previously unknown conformationally rigid sultams fused with the cyclobutane ring was developed. The key transformation was an intramolecular photochemical cyclization of linear sulfonamides. Crystallographic analysis showed that the obtained structures populated the uncharted region in the chemical space.
RESUMO
A one-step synthesis of functionalized 3-azabicyclo[3.2.0]heptanes by [2+2]-photochemical intermolecular cycloaddition of N-benzylmaleimide to alkenes was elaborated. The obtained compounds were easily transformed into the bi- and tricyclic analogues of piperidine, morpholine, piperazine, and GABA, which are advanced building blocks for drug discovery.
RESUMO
We have developed a rapid two-step synthesis of substituted 3-azabicyclo[3.2.0]heptanes which are attractive building blocks for drug discovery. This new method utilizes very common chemicals, benzaldehyde, allylamine, and cinnamic acid, via intramolectular [2+2]-photochemical cyclization.
Assuntos
Benzaldeídos/síntese química , Cinamatos/síntese química , Descoberta de Drogas , Benzaldeídos/química , Cinamatos/química , Ciclização , Estrutura Molecular , Processos Fotoquímicos , SolubilidadeRESUMO
An efficient two-step multigram synthesis of the previously unknown 3-benzyl-3-azabicyclo[3.1.1]heptan-6-one is described. The compound is shown to be a promising building block for further selective derivatization of the cyclobutane ring providing novel conformationally restricted piperidine derivatives.
