Csp 2 -Csp 2 and Csp 2 -N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives

A novel, sequential, palladium-catalyzed, cross-coupling reaction using N-tosylhydrazone and bromonitrobenzene derivatives followed by reductive cyclization has been developed. This transformation providing an efficient route to unexpected N-arylindole derivatives involves, in a one-pot reaction, th...

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Published inOrganic letters Vol. 19; no. 24; pp. 6700 - 6703
Main Authors Bzeih, Tourin, Lamaa, Diana, Frison, Gilles, Hachem, Ali, Jaber, Nada, Bignon, Jerome, Retailleau, Pascal, Alami, Mouad, Hamze, Abdallah
Format Journal Article
LanguageEnglish
Published United States 15.12.2017
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Summary:A novel, sequential, palladium-catalyzed, cross-coupling reaction using N-tosylhydrazone and bromonitrobenzene derivatives followed by reductive cyclization has been developed. This transformation providing an efficient route to unexpected N-arylindole derivatives involves, in a one-pot reaction, the formation of one Csp -Csp bond and two Csp -N bonds together with the cleavage of one Csp -heteroatom bond. Evaluation of the biological activity led to the identification of compound 5a, which displays potent activity at nanomolar concentrations against human colon carcinoma cell line.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.7b03422