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Heterocyclic photorearrangements. Photochemical behaviour of some 3,5‐disubstituted 1,2,4‐oxadiazoles in methanol at 254 nm
Author(s) -
Buscemi Silvestre,
Cicero Maria G.,
Vivoicolò,
Caronna Tullio
Publication year - 1988
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570250344
Subject(s) - chemistry , photoisomerization , substituent , methanol , ring (chemistry) , oxadiazole , photochemistry , nucleophile , benzimidazole , solvent , medicinal chemistry , organic chemistry , isomerization , catalysis
Photochemical behaviour of some 3,5‐disubstituted 1,2,4‐oxadiazoles in methanol at 254 nm has been investigated. Ring photoisomerization to the 1,3,4‐oxadiazole heterocycle or formation of open chain compounds involving the nucleophilic solvent was shown to depend on the nature and the position of the substituent. Photoinduced ring closure into the benzimidazole system, involving a 3‐ N ‐phenylamino side chain sequence and a photolytic intermediate of the oxadiazole heterocycle, is also reported.