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

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

Research output: Contribution to journalArticle

3 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)4450-4454
Number of pages5
JournalTetrahedron Letters
Volume58
Issue number47
DOIs
StatePublished - Nov 22 2017

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Acetals
Triazoles
Azides
Electrons
Substitution reactions
Acids

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Tandem synthesis of 1-formyl-1,2,3-triazoles. / Fletcher, James T.; Christensen, Joseph A.; Villa, Eric.

In: Tetrahedron Letters, Vol. 58, No. 47, 22.11.2017, p. 4450-4454.

Research output: Contribution to journalArticle

Fletcher, James T. ; Christensen, Joseph A. ; Villa, Eric. / Tandem synthesis of 1-formyl-1,2,3-triazoles. In: Tetrahedron Letters. 2017 ; Vol. 58, No. 47. pp. 4450-4454.
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