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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.

SUBMITTER: Fletcher JT

PROVIDER: S-EPMC5798646 | biostudies-literature | 2017 Nov

REPOSITORIES: biostudies-literature

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

Fletcher James T JT Christensen Joseph A JA Villa Eric M EM

Tetrahedron letters 20171013 47

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, noteworth ...[more]

PMID: 29422697

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