Synthesis of 2-[(quinolin-8-yloxy)methyl]quinoline-3-carboxylic acid derivatives

Li, Yang; Gao, Wentao

doi:10.1515/hc-2013-0088

Heterocyclic Communications

2013

DOI: 10.1515/hc-2013-0088

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Synthesis of 2-[(quinolin-8-yloxy)methyl]quinoline-3-carboxylic acid derivatives

Yang Li

Wentao Gao

Abstract: A simple and concise one-pot protocol for the synthesis of carboxyl-substituted bisquinoline systems 3a-i is described. The approach involves the Williamson reaction of ethyl 2-(halomethyl)quinoline-3-carboxylates 4a-c with 8-hydroxyquinolines 5a-c followed by hydrolysis.

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Cited by 6 publications

References 33 publications

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A Simple and Facile Synthesis of 4‐Phenylquinoline‐fused Pyrrolidin‐2‐ones

Zou

2017

Journal of Heterocyclic Chem

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in Wiley Online Library (wileyonlinelibrary.com).In the present investigation, a simple and facile synthesis of a series of 4-phenylquinoline-fused pyrrolidin-2-ones, namely, 9-phenyl-2-substituted-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones is described, involving the tandem intermolecular C-N bond formation reaction between readily available ethyl 2-(chloromethyl)-4-phenylquinoline-3-carboxylate and various amines followed by in situ intramolecular C-N bond cyclization process in the presence of EtOH-AcOH (v/v, 10:1) solvent system as the reaction medium.

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A Simple and Facile Synthesis of 4‐Phenylquinoline‐fused Pyrrolidin‐2‐ones

Zou

2017

Journal of Heterocyclic Chem

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General and efficient one-pot synthesis of N-substituted 7-bromo-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones

Gao

2016

Chem Heterocycl Comp

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A general three-step one-pot synthesis of novel (E)-6-chloro-2-(aryl/hetarylvinyl)quinoline-3-carboxylic acids

Wang

Zou

2017

Mol Divers

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In this work, a facile and general three-step one-pot synthesis of structurally new (E)-6-chloro-2-(aryl/hetarylvinyl)quinoline-3-carboxylic acid derivatives has been achieved from easily available ethyl 6-chloro-2-(chloromethyl) quinoline-3-carboxylate and aromatic or heteroaromatic aldehydes. This strategy features simple one-pot operation, tolerance of a wide range of substituents, and good yields. Moreover, these newly synthesized compounds belong to a new class of quinoline derivatives and could be good candidates for the development of more complex quinoline compounds for use in medicinal chemistry.

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Synthesis of 2-[(quinolin-8-yloxy)methyl]quinoline-3-carboxylic acid derivatives

Abstract: A simple and concise one-pot protocol for the synthesis of carboxyl-substituted bisquinoline systems 3a-i is described. The approach involves the Williamson reaction of ethyl 2-(halomethyl)quinoline-3-carboxylates 4a-c with 8-hydroxyquinolines 5a-c followed by hydrolysis.

Cited by 6 publications

References 33 publications

A Simple and Facile Synthesis of 4‐Phenylquinoline‐fused Pyrrolidin‐2‐ones

A Simple and Facile Synthesis of 4‐Phenylquinoline‐fused Pyrrolidin‐2‐ones

General and efficient one-pot synthesis of N-substituted 7-bromo-2,3-dihydro-1H-pyrrolo[3,4-b]quinolin-1-ones

A general three-step one-pot synthesis of novel (E)-6-chloro-2-(aryl/hetarylvinyl)quinoline-3-carboxylic acids

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