TY - JOUR
T1 - Tandem synthesis of 1-formyl-1,2,3-triazoles
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
Publisher Copyright:
© 2017 Elsevier Ltd
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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U2 - 10.1016/j.tetlet.2017.10.023
DO - 10.1016/j.tetlet.2017.10.023
M3 - Article
AN - SCOPUS:85031667598
VL - 58
SP - 4450
EP - 4454
JO - Tetrahedron Letters
JF - Tetrahedron Letters
SN - 0040-4039
IS - 47
ER -