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 | |
| State | Published - Nov 22 2017 |
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All Science Journal Classification (ASJC) codes
- Biochemistry
- Drug Discovery
- Organic Chemistry
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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 journal › Article
}
TY - JOUR
T1 - Tandem synthesis of 1-formyl-1,2,3-triazoles
AU - Fletcher, James T.
AU - Christensen, Joseph A.
AU - Villa, Eric
PY - 2017/11/22
Y1 - 2017/11/22
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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UR - http://www.scopus.com/inward/citedby.url?scp=85031667598&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2017.10.023
DO - 10.1016/j.tetlet.2017.10.023
M3 - Article
VL - 58
SP - 4450
EP - 4454
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 47
ER -