RESUMO
Indole aziridines and their hydroxyl derivatives have been used for the preparation of a small library of novel functionalized bisindoles. Diversification of these building blocks by solvent-free C-C-bond formation on solid support yielded annulated Hymenialdisine analogues under mild reaction conditions. Indoles as C-nucleophiles form potentially pharmacologically active bisindoles through an electrophilic aromatic substitution pathway in good to excellent yields. Further transformations of the indole aziridines with H-, N-, and O-nucleophiles demonstrate their versatility as key intermediates in diversity oriented synthesis. The hydroxyl precursor leads also to unsymmetrical bisindoles under similar reaction conditions. Important intermediates and final library compounds were confirmed by X-ray analysis. Theoretical studies on these systems show the possible cationic intermediate in the substitution pathway.
Assuntos
Indóis , Cristalografia por Raios X , Indóis/síntese química , Indóis/química , Espectroscopia de Ressonância Magnética/métodos , Modelos Moleculares , Estrutura Molecular , Bibliotecas de Moléculas Pequenas , EstereoisomerismoRESUMO
A general copper-catalyzed method for the sulfonylation of arylboronic acids with sulfinate salts is described. A variety of alkyl-aryl, diaryl, and alkyl-heteroaryl sulfones were synthesized in good yield.
Assuntos
Ácidos Borônicos/química , Catálise , Cobre/química , Ácidos Sulfínicos/químicaRESUMO
Novel unsymmetrical bisindoles were synthesized by a solvent-free C-C bond-formation reaction under mild conditions. Starting from aziridines or hydroxyl precursors, indoles have been used as C-nucleophiles to form new pharmacologically interesting bisindoles via an electrophilic aromatic substitution pathway in good to excellent yields. [reaction: see text]
