Tandem synthesis of 1-formyl-1,2,3-triazoles

James T. Fletcher; Joseph A. Christensen; Eric M. Villa

doi:10.1016/j.tetlet.2017.10.023

Tandem synthesis of 1-formyl-1,2,3-triazoles

James T. Fletcher, Joseph A. Christensen, Eric M. Villa

Department of Chemistry

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

8 Scopus citations

Abstract

A tandem method for preparing 4-formyl-1,2,3-triazoles via a two-step one-pot acetal cleavage/CuAAC reaction was developed. Using this method, 4-formyl-1,2,3-triazole analogs with both electron-withdrawing and electron-donating substituents were prepared in good yield and purity. Expansion of this method to a three-step tandem reaction that incorporates an additional step of azide substitution was also successful, circumventing the need for organic azide isolation. This one-pot method, noteworthy in its simplicity and mild conditions, utilizes practical, readily available reactants and relies on protic solvent to promote acid-catalyzed acetal cleavage.

Original language	English (US)
Pages (from-to)	4450-4454
Number of pages	5
Journal	Tetrahedron Letters
Volume	58
Issue number	47
DOIs	https://doi.org/10.1016/j.tetlet.2017.10.023
State	Published - Nov 22 2017

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Tandem synthesis of 1-formyl-1,2,3-triazoles",

abstract = "A tandem method for preparing 4-formyl-1,2,3-triazoles via a two-step one-pot acetal cleavage/CuAAC reaction was developed. Using this method, 4-formyl-1,2,3-triazole analogs with both electron-withdrawing and electron-donating substituents were prepared in good yield and purity. Expansion of this method to a three-step tandem reaction that incorporates an additional step of azide substitution was also successful, circumventing the need for organic azide isolation. This one-pot method, noteworthy in its simplicity and mild conditions, utilizes practical, readily available reactants and relies on protic solvent to promote acid-catalyzed acetal cleavage.",

author = "Fletcher, {James T.} and Christensen, {Joseph A.} and Villa, {Eric M.}",

note = "Funding Information: This publication was made possible by grants from the National Institute for General Medical Science ( NIGMS ) ( 5P20GM103427 ), a component of the National Institutes of Health (NIH), and its contents are the sole responsibility of the authors and do not necessarily represent the official views of NIGMS or NIH. JAC acknowledges Creighton University {\textquoteright}s Baumann Family Scholarship for financial support. A ",

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AU - Fletcher, James T.

AU - Christensen, Joseph A.

AU - Villa, Eric M.

N1 - Funding Information: This publication was made possible by grants from the National Institute for General Medical Science ( NIGMS ) ( 5P20GM103427 ), a component of the National Institutes of Health (NIH), and its contents are the sole responsibility of the authors and do not necessarily represent the official views of NIGMS or NIH. JAC acknowledges Creighton University ’s Baumann Family Scholarship for financial support. A

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N2 - A tandem method for preparing 4-formyl-1,2,3-triazoles via a two-step one-pot acetal cleavage/CuAAC reaction was developed. Using this method, 4-formyl-1,2,3-triazole analogs with both electron-withdrawing and electron-donating substituents were prepared in good yield and purity. Expansion of this method to a three-step tandem reaction that incorporates an additional step of azide substitution was also successful, circumventing the need for organic azide isolation. This one-pot method, noteworthy in its simplicity and mild conditions, utilizes practical, readily available reactants and relies on protic solvent to promote acid-catalyzed acetal cleavage.

AB - A tandem method for preparing 4-formyl-1,2,3-triazoles via a two-step one-pot acetal cleavage/CuAAC reaction was developed. Using this method, 4-formyl-1,2,3-triazole analogs with both electron-withdrawing and electron-donating substituents were prepared in good yield and purity. Expansion of this method to a three-step tandem reaction that incorporates an additional step of azide substitution was also successful, circumventing the need for organic azide isolation. This one-pot method, noteworthy in its simplicity and mild conditions, utilizes practical, readily available reactants and relies on protic solvent to promote acid-catalyzed acetal cleavage.

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