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

被引：16

作者：

Bzeih, Tourin ^{[1
,2
,3
]}

Lamaa, Diana ^{[1
]}

Frison, Gilles ^{[4
]}

Hachem, Ali ^{[2
,3
]}

Jaber, Nada ^{[2
,3
]}

Bignon, Jerome ^{[5
]}

Retailleau, Pascal ^{[5
]}

Alami, Mouad ^{[1
]}

Hamze, Abdallah ^{[1
]}

机构：

[1] Univ Paris Saclay, CNRS, Univ Paris Sud, BioCIS, F-92290 Chatenay Malabry, France

[2] Lebanese Univ, Fac Sci 1, Lab Med Chem, Beirut, Lebanon

[3] Lebanese Univ, PRASE EDST, Beirut, Lebanon

[4] Univ Paris Saclay, Ecole Polytech, CNRS, LCM, F-91128 Palaiseau, France

[5] CNRS, UPR 2301, Inst Chim Subst Nat, F-91198 Gif Sur Yvette, France

来源：

ORGANIC LETTERS | 2017年 / 19卷 / 24期

关键词：

CROSS-COUPLING REACTIONS; AMINES SYNTHESIS; HYDRAZONES; CHEMISTRY; 1,1-DIARYLETHYLENES; ARYLINDOLES; REAGENTS; ROUTE;

D O I：

10.1021/acs.orglett.7b03422

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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(2)-Csp(2) bond and two Csp(2)-N bonds together with the cleavage of one Csp(2)-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.

引用

页码：6700 / 6703

页数：4

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