Csp2-Csp2 and Csp2-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives

Tourin Bzeih; Diana Lamaa; Gilles Frison; Ali Hachem; Nada Jaber; Jerome Bignon; Pascal Retailleau; Mouad Alami; Abdallah Hamze

doi:10.1021/acs.orglett.7b03422

Csp²-Csp² and Csp²-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives

Tourin Bzeih, Diana Lamaa, Gilles Frison, Ali Hachem, Nada Jaber, Jerome Bignon, Pascal Retailleau, Mouad Alami, Abdallah Hamze

Research output: Contribution to journal › Article › peer-review

Abstract

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 Csp²-Csp² bond and two Csp²-N bonds together with the cleavage of one Csp²-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.

Original language	English
Pages (from-to)	6700-6703
Number of pages	4
Journal	Organic Letters
Volume	19
Issue number	24
DOIs	https://doi.org/10.1021/acs.orglett.7b03422
Publication status	Published - 15 Dec 2017
Externally published	Yes

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title = "Csp2-Csp2 and Csp2-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives",

abstract = "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 Csp2-Csp2 bond and two Csp2-N bonds together with the cleavage of one Csp2-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.",

author = "Tourin Bzeih and Diana Lamaa and Gilles Frison and Ali Hachem and Nada Jaber and Jerome Bignon and Pascal Retailleau and Mouad Alami and Abdallah Hamze",

note = "Publisher Copyright: {\textcopyright} 2017 American Chemical Society.",

year = "2017",

month = dec,

day = "15",

doi = "10.1021/acs.orglett.7b03422",

language = "English",

volume = "19",

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journal = "Organic Letters",

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TY - JOUR

T1 - Csp2-Csp2 and Csp2-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes

T2 - An Unexpected Cyclization to Substituted Indole Derivatives

AU - Bzeih, Tourin

AU - Lamaa, Diana

AU - Frison, Gilles

AU - Hachem, Ali

AU - Jaber, Nada

AU - Bignon, Jerome

AU - Retailleau, Pascal

AU - Alami, Mouad

AU - Hamze, Abdallah

PY - 2017/12/15

Y1 - 2017/12/15

N2 - 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 Csp2-Csp2 bond and two Csp2-N bonds together with the cleavage of one Csp2-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.

AB - 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 Csp2-Csp2 bond and two Csp2-N bonds together with the cleavage of one Csp2-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.

U2 - 10.1021/acs.orglett.7b03422

DO - 10.1021/acs.orglett.7b03422

M3 - Article

C2 - 29206470

AN - SCOPUS:85038424909

SN - 1523-7060

VL - 19

SP - 6700

EP - 6703

JO - Organic Letters

JF - Organic Letters

IS - 24

ER -

Csp2-Csp2 and Csp2-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives

Abstract

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Csp²-Csp² and Csp²-N Bond Formation in a One-Pot Reaction between N-Tosylhydrazones and Bromonitrobenzenes: An Unexpected Cyclization to Substituted Indole Derivatives