Theoretical study of photoinduced ring-isomerization in the 1,2,4-oxadiazole series

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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.
Lingua originaleEnglish
pagine (da-a)3243-3249
Numero di pagine7
RivistaTetrahedron
Volume60
Stato di pubblicazionePublished - 2004

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All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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