TY - JOUR
T1 - Rapid, microwave accelerated synthesis of [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles from 4-acylamino-1,2,4-triazoles
AU - Breunig, Stephanie L.
AU - Olson, Margaret E.
AU - Harki, Daniel A.
N1 - Publisher Copyright:
© 2016 Elsevier Ltd
PY - 2016
Y1 - 2016
N2 - 1,2,4-Triazoles and 1,3,4-oxadiazoles are prevalent moieties in pharmaceutical agents, yet fused [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles are surprisingly under-represented for both synthesis and biological application. We report a rapid, two-step synthesis of [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles from commercial 4-amino-1,2,4-triazoles that is highlighted by a microwave accelerated intramolecular cyclization to generate the fused ring system. Our efforts to optimize reaction conditions and elucidate reaction mechanism are also described.
AB - 1,2,4-Triazoles and 1,3,4-oxadiazoles are prevalent moieties in pharmaceutical agents, yet fused [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles are surprisingly under-represented for both synthesis and biological application. We report a rapid, two-step synthesis of [1,2,4]triazolo[3,4-b][1,3,4]oxadiazoles from commercial 4-amino-1,2,4-triazoles that is highlighted by a microwave accelerated intramolecular cyclization to generate the fused ring system. Our efforts to optimize reaction conditions and elucidate reaction mechanism are also described.
KW - 1,2,4-Triazole
KW - 1,3,4-Oxadiazole
KW - Intramolecular cyclization
KW - Microwave chemistry
KW - [1,2,4]Triazolo[3,4-b][1,3,4]oxadiazole
UR - http://www.scopus.com/inward/record.url?scp=84981333818&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84981333818&partnerID=8YFLogxK
U2 - 10.1016/j.tetlet.2016.07.082
DO - 10.1016/j.tetlet.2016.07.082
M3 - Article
C2 - 28138199
AN - SCOPUS:84981333818
SN - 0040-4039
VL - 57
SP - 4056
EP - 4060
JO - Tetrahedron Letters
JF - Tetrahedron Letters
IS - 36
ER -