Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates

Kavitha Sudheendran; Dietmar Schmidt; Wolfgang Frey; Jürgen Conrad; Uwe Beifuss

doi:10.1016/j.tet.2014.01.019

Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates

Kavitha Sudheendran
, Dietmar Schmidt
, Wolfgang Frey
, Jürgen Conrad
, Uwe Beifuss

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

38 Scopus citations

Abstract

Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)₂-catalyzed reaction between two amidines using NaHCO₃ as a base, 1,10-phenanthroline as an additive and K₃[Fe(CN)₆]/ atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4- triazoles with yields up to 64% rests on the Cu(OTf)₂-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step.

Original language	English
Pages (from-to)	1635-1645
Number of pages	11
Journal	Tetrahedron
Volume	70
Issue number	8
DOIs	https://doi.org/10.1016/j.tet.2014.01.019
State	Published - 25 Feb 2014
Externally published	Yes

Keywords

1,2,4-Triazole
Amidine
Catalysis
Copper
Imidate

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2014.01.019

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title = "Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates",

abstract = "Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)2-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K3[Fe(CN)6]/ atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68\%. The second procedure for the synthesis of 3,5-diaryl-1,2,4- triazoles with yields up to 64\% rests on the Cu(OTf)2-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step.",

keywords = "1,2,4-Triazole, Amidine, Catalysis, Copper, Imidate",

author = "Kavitha Sudheendran and Dietmar Schmidt and Wolfgang Frey and J{\"u}rgen Conrad and Uwe Beifuss",

year = "2014",

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doi = "10.1016/j.tet.2014.01.019",

language = "English",

volume = "70",

pages = "1635--1645",

journal = "Tetrahedron",

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T1 - Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates

AU - Sudheendran, Kavitha

AU - Schmidt, Dietmar

AU - Frey, Wolfgang

AU - Conrad, Jürgen

AU - Beifuss, Uwe

PY - 2014/2/25

Y1 - 2014/2/25

N2 - Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)2-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K3[Fe(CN)6]/ atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4- triazoles with yields up to 64% rests on the Cu(OTf)2-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step.

AB - Two methods for the synthesis of 3,5-diaryl-1,2,4-triazoles, both domino reactions, are reported. The first procedure, the Cu(OTf)2-catalyzed reaction between two amidines using NaHCO3 as a base, 1,10-phenanthroline as an additive and K3[Fe(CN)6]/ atmospheric oxygen as the oxidant, delivers 3,5-diaryl-1,2,4-triazoles with yields up to 68%. The second procedure for the synthesis of 3,5-diaryl-1,2,4- triazoles with yields up to 64% rests on the Cu(OTf)2-catalyzed reaction between two imidates and ammonium carbonate. This method features the formation of three bonds in a single synthetic step.

KW - 1,2,4-Triazole

KW - Amidine

KW - Catalysis

KW - Copper

KW - Imidate

UR - https://www.scopus.com/pages/publications/84893511872

U2 - 10.1016/j.tet.2014.01.019

DO - 10.1016/j.tet.2014.01.019

M3 - Article

AN - SCOPUS:84893511872

SN - 0040-4020

VL - 70

SP - 1635

EP - 1645

JO - Tetrahedron

JF - Tetrahedron

IS - 8

ER -

Facile synthesis of 3,5-diaryl-1,2,4-triazoles via copper-catalyzed domino nucleophilic substitution/oxidative cyclization using amidines or imidates as substrates

Abstract

Keywords

ASJC Scopus subject areas

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