Site-Selective C8-Alkylation of Quinoline N-Oxides with Maleimides under Rh(III) Catalysis

Won An; Suk Hun Lee; Dayoung Kim; Harin Oh; Suho Kim; Youjung Byun; Hyun Jin Kim; Neeraj Kumar Mishra; In Su Kim

doi:10.1021/acs.joc.1c00612

Site-Selective C8-Alkylation of Quinoline N-Oxides with Maleimides under Rh(III) Catalysis

Won An
, Suk Hun Lee
, Dayoung Kim
, Harin Oh
, Suho Kim
, Youjung Byun
, Hyun Jin Kim
, Neeraj Kumar Mishra
, In Su Kim

Department of Pharmacy

Sungkyunkwan University
Korea Research Institute of Chemical Technology

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

17 Scopus citations

Abstract

The site-selective modification of quinolines and their analogs has emerged as a pivotal topic in medicinal chemistry and drug discovery. Herein, we describe the rhodium(III)-catalyzed C8-alkylation of quinoline N-oxides with maleimides as alkylating agents, resulting in the formation of bioactive succinimide-containing quinoline derivatives. The reaction proceeds under mild conditions with complete functional group tolerance.

Original language	English
Pages (from-to)	7579-7587
Number of pages	9
Journal	Journal of Organic Chemistry
Volume	86
Issue number	11
DOIs	https://doi.org/10.1021/acs.joc.1c00612
State	Published - 4 Jun 2021

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title = "Site-Selective C8-Alkylation of Quinoline N-Oxides with Maleimides under Rh(III) Catalysis",

abstract = "The site-selective modification of quinolines and their analogs has emerged as a pivotal topic in medicinal chemistry and drug discovery. Herein, we describe the rhodium(III)-catalyzed C8-alkylation of quinoline N-oxides with maleimides as alkylating agents, resulting in the formation of bioactive succinimide-containing quinoline derivatives. The reaction proceeds under mild conditions with complete functional group tolerance.",

author = "Won An and Lee, \{Suk Hun\} and Dayoung Kim and Harin Oh and Suho Kim and Youjung Byun and Kim, \{Hyun Jin\} and Mishra, \{Neeraj Kumar\} and Kim, \{In Su\}",

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doi = "10.1021/acs.joc.1c00612",

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T1 - Site-Selective C8-Alkylation of Quinoline N-Oxides with Maleimides under Rh(III) Catalysis

AU - An, Won

AU - Lee, Suk Hun

AU - Kim, Dayoung

AU - Oh, Harin

AU - Kim, Suho

AU - Byun, Youjung

AU - Kim, Hyun Jin

AU - Mishra, Neeraj Kumar

AU - Kim, In Su

PY - 2021/6/4

Y1 - 2021/6/4

N2 - The site-selective modification of quinolines and their analogs has emerged as a pivotal topic in medicinal chemistry and drug discovery. Herein, we describe the rhodium(III)-catalyzed C8-alkylation of quinoline N-oxides with maleimides as alkylating agents, resulting in the formation of bioactive succinimide-containing quinoline derivatives. The reaction proceeds under mild conditions with complete functional group tolerance.

AB - The site-selective modification of quinolines and their analogs has emerged as a pivotal topic in medicinal chemistry and drug discovery. Herein, we describe the rhodium(III)-catalyzed C8-alkylation of quinoline N-oxides with maleimides as alkylating agents, resulting in the formation of bioactive succinimide-containing quinoline derivatives. The reaction proceeds under mild conditions with complete functional group tolerance.

UR - https://www.scopus.com/pages/publications/85106509889

U2 - 10.1021/acs.joc.1c00612

DO - 10.1021/acs.joc.1c00612

M3 - Article

AN - SCOPUS:85106509889

SN - 0022-3263

VL - 86

SP - 7579

EP - 7587

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 11

ER -

Site-Selective C8-Alkylation of Quinoline N-Oxides with Maleimides under Rh(III) Catalysis

Abstract

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