NaClO‐Mediated Cross Installation of Indoles and Azoles Benefits Anticancer Hit Discovery DOI

Changjun Yu,

E Ruiyao,

Xiaowei Zhang

et al.

ChemMedChem, Journal Year: 2022, Volume and Issue: 18(5)

Published: Dec. 31, 2022

Innovations in synthetic chemistry have a profound impact on the drug discovery process, and will always be necessary driver of development. As result, it is significance to develop novel simple effective installation medicinal modules promote discovery. Herein, we developed NaClO-mediated cross indoles azoles, both which are frequently encountered drugs natural products. This toolbox provides convenient route access library N-linked 2-(azol-1-yl) indole derivatives, can used for late-stage modification drugs, products peptides. Moreover, biological screening has revealed that several adducts showed promising anticancer activities against A549 NCI-H1975 cells, give us hit

Language: Английский

Iodine-dependent oxidative regioselective aminochalcogenation of indolines DOI
Xiaoxiang Zhang, Chenrui Liu, Wanxing Wei

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(9), P. 1152 - 1155

Published: Jan. 1, 2024

An efficient approach for the selective construction of C2,3- or C2,5-aminochalcogenated indole derivatives has been developed, which enables oxidative regioselective aminochalcogenation indolines with amines and dichalconides.

Language: Английский

Citations

7

Iodine-mediated oxidative triple functionalization of indolines with azoles and diazonium salts DOI
Yifeng Liu,

Xiaoting Gu,

Xiaoxiang Zhang

et al.

Chemical Communications, Journal Year: 2024, Volume and Issue: 60(34), P. 4613 - 4616

Published: Jan. 1, 2024

We report an innovative synthetic strategy for the generation of polysubstituted indoles from indolines, aryldiazonium salts, and azoles. The methodology encompasses electrophilic substitution reaction affording C5-indoline intermediates which undergo iodine-mediated oxidative transformation coupled with C-H functionalization to yield indole derivatives.

Language: Английский

Citations

7

Intermolecular C–H Aminocyanation of Indoles via Copper–iodine Cocatalyzed Tandem C–N/C–C Bond Formation DOI
Wenhua Yu, Xiaoxiang Zhang, Chenrui Liu

et al.

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(18), P. 12424 - 12433

Published: Sept. 1, 2022

An efficient copper–iodine cocatalyzed intermolecular C–H aminocyanation of indoles with a broad substrate scope has been developed for the first time. This method enables highly step-economic access to 2-amino-3-cyanoindoles in moderate good yields and provides complementary strategy regioselective difunctionalization carbon═carbon double bonds interest organic synthesis related areas. Mechanistic studies suggest that these transformations are initiated by iodine-mediated C2–H amination azoles, followed copper-catalyzed C3–H cyanation ethyl cyanoformate.

Language: Английский

Citations

17

Iron–iodine co-catalysis towards tandem C–N/C–C bond formation: one-pot regioselective synthesis of 2-amino-3-alkylindoles DOI
Yingying Zhang, Yating Huang,

Kewei Yu

et al.

Organic Chemistry Frontiers, Journal Year: 2022, Volume and Issue: 9(22), P. 6165 - 6171

Published: Jan. 1, 2022

An efficient intermolecular C2,3-H aminoalkylation of indoles with 9 H -xanthenes and azoles via iron–iodine co-catalyzed tandem C–N/C–C bond formation has been developed.

Language: Английский

Citations

15

Iodine-Mediated C2,3–H Aminoheteroarylation of Indoles DOI

Maoyi Dai,

Yingying Zhang, Xiaoxiang Zhang

et al.

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(21), P. 15106 - 15117

Published: Oct. 21, 2023

A metal-free one-pot oxidative cross-dehydrogenation coupling reaction for the formation of C-N/C-C bonds at C2,3-positions indoles with azoles and quinoxalinones has been developed. The proposed method several notable features, including catalysis, use N-H free as substrates, ease operation, mild conditions, compatibility a wide range substrates.

Language: Английский

Citations

9

Solvent-controlled switchable multicomponent tandem oxidative triple functionalization of indolines DOI
Xiaoxiang Zhang, Xiaoting Gu, Yingying Zhang

et al.

Organic Chemistry Frontiers, Journal Year: 2024, Volume and Issue: 11(7), P. 1933 - 1940

Published: Jan. 1, 2024

A new one-pot method for solvent-controlled switchable tandem oxidative triple functionalization of indolines has been developed via successive regioselective chalcogenation, oxidation, amination and halogenation.

Language: Английский

Citations

3

Iron-Catalyzed Friedel–Crafts-type 3,5-Diacylation of Indoles DOI

Xiaoting Gu,

Maoyi Dai,

Xirui Qing

et al.

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(14), P. 10272 - 10282

Published: July 5, 2024

The exploration of remote functionalization indoles is impeded by the inherently dominant reactivity intrinsic to pyrrole moiety. Herein, we delineate a novel strategy facilitated Lewis acid mediation, enabling C-H functionalization, which culminates in synthesis an array selectively functionalized indole derivatives, encompassing 3-trifluoroacetyl and 5-benzoyl motifs, utilizing trifluoroacetic anhydride various acyl chlorides. Notably, protocol exhibits versatility, as epitomized extension C5-acylation alkylation sulfonation reactions. This methodology distinguished its exemplary regio- chemo-selectivity, extensive substrate scope, commendable tolerance diverse functional groups, employment comparatively mild reaction conditions.

Language: Английский

Citations

3

One-pot Multicomponent Tandem Reaction for the Rapid Synthesis of 2-Amino-3-benzylindoles DOI
Pengyan Zhang, Chenrui Liu,

Maoyi Dai

et al.

Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown

Published: Jan. 1, 2025

A novel one-pot oxidative cross-dehydrogenation coupling (CDC) reaction has been developed for the selective construction of C–N and C–C bonds at C2,3-positions indoles.

Language: Английский

Citations

0

Pd(II)/Cu(I) Co-catalyzed Dual C–H Functionalization of Indoles at C2 and C3 Positions Using Bifunctional Arylsulfonyl Reagents DOI
Jiahui Huang,

Xiujuan Ai,

Shuai Zhou

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 20, 2025

A Pd(II)/Cu(I) co-catalyzed dual C-H functionalization strategy enables the one-pot synthesis of C2/C3-difunctionalized indoles using arylsulfonyl reagents. In this method, Cu(I) reduces S(VI) reagents to generate radicals, which react with Pd(II) form electrophilic Ar-Pd(III) intermediates. These intermediates regioselectively arylate at C2 position, followed by Cu(II)-mediated C3 deliver final products. This synergistic method enhances efficiency, waste, and streamlines complex indole functionalization.

Language: Английский

Citations

0

Synthesis of 2,3‐Diaminoindolesvia a Copper‐Iodine Co‐catalytic Strategy DOI
Wenhua Yu, Yingying Zhang, Xiaoxiang Zhang

et al.

Chinese Journal of Chemistry, Journal Year: 2023, Volume and Issue: 41(24), P. 3567 - 3572

Published: Aug. 28, 2023

Comprehensive Summary A one‐pot synthesis of vicinal diamines using indoles, azoles and phenothiazines in a tandem multi‐component reaction is developed. The utilization copper‐iodine co‐catalytic system enables the generation diverse range diaminoindoles with good selectivity moderate to yields. An attractive aspect this method that it can be conducted under mild environmentally friendly conditions, showcasing its potential as an alternative approach for synthesizing diamines. Moreover, use multicomponent highlights power versatility such strategies synthetic chemistry.

Language: Английский

Citations

8