Ytterbium(III) triflate catalyzed domino reaction of arylamines and styrene oxides: Synthesis of 2-benzyl-3-arylquinoline derivatives

Saghir Ali; Abu Taleb Khan

doi:10.1016/j.tetlet.2021.152981

Ytterbium(III) triflate catalyzed domino reaction of arylamines and styrene oxides: Synthesis of 2-benzyl-3-arylquinoline derivatives

Saghir Ali, Abu Taleb Khan

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

8 Scopus citations

Abstract

An efficient and straightforward method for the synthesis of 2-benzyl-3-arylquinoline derivatives is reported involving the domino reaction of substituted arylamines and styrene oxides in the presence of 10 mol% ytterbium(III) triflate in acetonitrile at 80 °C. Additionally, the reaction of aliphatic epoxides with p-anisidine provided 2,3-dialkylquinoline derivatives under identical reaction conditions. Important features of the protocol are ease of handling, broad substrate scope, good yields, and the formation of two C[sbnd]N and two C[sbnd]C bonds.

Original language	English (US)
Article number	152981
Journal	Tetrahedron Letters
Volume	70
DOIs	https://doi.org/10.1016/j.tetlet.2021.152981
State	Published - Apr 27 2021
Externally published	Yes

Keywords

Arylamines
Atom-economy
Domino reaction
Easy handling
Styrene oxides

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tetlet.2021.152981

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title = "Ytterbium(III) triflate catalyzed domino reaction of arylamines and styrene oxides: Synthesis of 2-benzyl-3-arylquinoline derivatives",

abstract = "An efficient and straightforward method for the synthesis of 2-benzyl-3-arylquinoline derivatives is reported involving the domino reaction of substituted arylamines and styrene oxides in the presence of 10 mol% ytterbium(III) triflate in acetonitrile at 80 °C. Additionally, the reaction of aliphatic epoxides with p-anisidine provided 2,3-dialkylquinoline derivatives under identical reaction conditions. Important features of the protocol are ease of handling, broad substrate scope, good yields, and the formation of two C[sbnd]N and two C[sbnd]C bonds.",

keywords = "Arylamines, Atom-economy, Domino reaction, Easy handling, Styrene oxides",

author = "Saghir Ali and Khan, {Abu Taleb}",

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T1 - Ytterbium(III) triflate catalyzed domino reaction of arylamines and styrene oxides

T2 - Synthesis of 2-benzyl-3-arylquinoline derivatives

AU - Ali, Saghir

AU - Khan, Abu Taleb

PY - 2021/4/27

Y1 - 2021/4/27

N2 - An efficient and straightforward method for the synthesis of 2-benzyl-3-arylquinoline derivatives is reported involving the domino reaction of substituted arylamines and styrene oxides in the presence of 10 mol% ytterbium(III) triflate in acetonitrile at 80 °C. Additionally, the reaction of aliphatic epoxides with p-anisidine provided 2,3-dialkylquinoline derivatives under identical reaction conditions. Important features of the protocol are ease of handling, broad substrate scope, good yields, and the formation of two C[sbnd]N and two C[sbnd]C bonds.

AB - An efficient and straightforward method for the synthesis of 2-benzyl-3-arylquinoline derivatives is reported involving the domino reaction of substituted arylamines and styrene oxides in the presence of 10 mol% ytterbium(III) triflate in acetonitrile at 80 °C. Additionally, the reaction of aliphatic epoxides with p-anisidine provided 2,3-dialkylquinoline derivatives under identical reaction conditions. Important features of the protocol are ease of handling, broad substrate scope, good yields, and the formation of two C[sbnd]N and two C[sbnd]C bonds.

KW - Arylamines

KW - Atom-economy

KW - Domino reaction

KW - Easy handling

KW - Styrene oxides

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Ytterbium(III) triflate catalyzed domino reaction of arylamines and styrene oxides: Synthesis of 2-benzyl-3-arylquinoline derivatives

Abstract

Keywords

ASJC Scopus subject areas

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