6533b834fe1ef96bd129d5b6
RESEARCH PRODUCT
Theoretical study of photoinduced ring-isomerization in the 1,2,4-oxadiazole series
Silvestre BuscemiIvana PibiriMaurizio D'auriaAndrea PaceNicolò Vivonasubject
Ab initio calculationPhotoisomerizationPhotochemistryChemistryHeterocycleOrganic ChemistryOxadiazoleSettore CHIM/06 - Chimica OrganicaPhotochemistryBiochemistrychemistry.chemical_compoundComputational chemistryAb initio quantum chemistry methodsPhotoisomerizationDrug Discovery124-OxadiazoleIsomerizationdescription
Abstract A theoretical study of photoinduced ring-isomerization of 3-amino-5-methyl- and 3-amino-5-phenyl-1,2,4-oxadiazoles is reported. The results well agree with the reported experimental data: in particular, they explain the ring-photoisomerization into the corresponding 2-amino-1,3,4-oxadiazoles through a ring contraction-ring expansion route; moreover, the occurrence of competing pathways involving both the ring contraction and the internal cyclization–isomerization mechanism during irradiation of the 5-alkyl substituted substrates in the presence of a base has been also substantiated.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 2004-03-01 | Tetrahedron |