Ruthenium(II)-catalyzed facile synthesis of 3-(phenylamino)-1H-indole-2-carboxylates from anilines and diazo pyruvates promoted by FeCl3

Farrukh Sajjad; Alavala Gopi Krishna Reddy; Dong Xing; Suzhen Dong; Wenhao Hu

doi:10.1016/j.tet.2020.131399

Ruthenium(II)-catalyzed facile synthesis of 3-(phenylamino)-1H-indole-2-carboxylates from anilines and diazo pyruvates promoted by FeCl₃

Farrukh Sajjad, Alavala Gopi Krishna Reddy, Dong Xing, Suzhen Dong, Wenhao Hu

School of Chemistry and Molecular Engineering

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

2 Scopus citations

Abstract

An unprecedented synthetic route towards a variety of 3-anilino-1H-indoles is accomplished from diazo pyruvates and anilines via a domino ruthenium-catalyzed annulation and subsequent iron promoted fragmentation and rearrangement. The current strategy was amenable to deliver diversely substituted indole esters, which were subjected to in vitro anti-cancer activity assessment using CCK-8 assay. Compound 4i displayed the best inhibition activity with IC₅₀ value of 0.05 μM, triggering the initiation towards discovering promising lead compounds in the future.

Original language	English
Article number	131399
Journal	Tetrahedron
Volume	77
DOIs	https://doi.org/10.1016/j.tet.2020.131399
State	Published - 1 Jan 2021

Keywords

Annulation
Anti-cancer activity
Diazo pyruvates
Indoles
Rearrangement

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This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1016/j.tet.2020.131399

Cite this

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title = "Ruthenium(II)-catalyzed facile synthesis of 3-(phenylamino)-1H-indole-2-carboxylates from anilines and diazo pyruvates promoted by FeCl3",

abstract = "An unprecedented synthetic route towards a variety of 3-anilino-1H-indoles is accomplished from diazo pyruvates and anilines via a domino ruthenium-catalyzed annulation and subsequent iron promoted fragmentation and rearrangement. The current strategy was amenable to deliver diversely substituted indole esters, which were subjected to in vitro anti-cancer activity assessment using CCK-8 assay. Compound 4i displayed the best inhibition activity with IC50 value of 0.05 μM, triggering the initiation towards discovering promising lead compounds in the future.",

keywords = "Annulation, Anti-cancer activity, Diazo pyruvates, Indoles, Rearrangement",

author = "Farrukh Sajjad and Reddy, \{Alavala Gopi Krishna\} and Dong Xing and Suzhen Dong and Wenhao Hu",

note = "Publisher Copyright: {\textcopyright} 2020",

year = "2021",

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day = "1",

doi = "10.1016/j.tet.2020.131399",

language = "英语",

volume = "77",

journal = "Tetrahedron",

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T1 - Ruthenium(II)-catalyzed facile synthesis of 3-(phenylamino)-1H-indole-2-carboxylates from anilines and diazo pyruvates promoted by FeCl3

AU - Sajjad, Farrukh

AU - Reddy, Alavala Gopi Krishna

AU - Xing, Dong

AU - Dong, Suzhen

AU - Hu, Wenhao

PY - 2021/1/1

Y1 - 2021/1/1

N2 - An unprecedented synthetic route towards a variety of 3-anilino-1H-indoles is accomplished from diazo pyruvates and anilines via a domino ruthenium-catalyzed annulation and subsequent iron promoted fragmentation and rearrangement. The current strategy was amenable to deliver diversely substituted indole esters, which were subjected to in vitro anti-cancer activity assessment using CCK-8 assay. Compound 4i displayed the best inhibition activity with IC50 value of 0.05 μM, triggering the initiation towards discovering promising lead compounds in the future.

AB - An unprecedented synthetic route towards a variety of 3-anilino-1H-indoles is accomplished from diazo pyruvates and anilines via a domino ruthenium-catalyzed annulation and subsequent iron promoted fragmentation and rearrangement. The current strategy was amenable to deliver diversely substituted indole esters, which were subjected to in vitro anti-cancer activity assessment using CCK-8 assay. Compound 4i displayed the best inhibition activity with IC50 value of 0.05 μM, triggering the initiation towards discovering promising lead compounds in the future.

KW - Annulation

KW - Anti-cancer activity

KW - Diazo pyruvates

KW - Indoles

KW - Rearrangement

UR - https://www.scopus.com/pages/publications/85097088342

U2 - 10.1016/j.tet.2020.131399

DO - 10.1016/j.tet.2020.131399

M3 - 文章

AN - SCOPUS:85097088342

SN - 0040-4020

VL - 77

JO - Tetrahedron

JF - Tetrahedron

M1 - 131399

ER -