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Paper | Regular issue | Vol 29, No. 7, 1989, pp.1301-1308
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4968
Heterocyclic Photorearrangements - Photochemical Behavior od Some 3-Acetylamino-5-aryl-1,2,4-oxadiazoles. A Photoinduced iso-Heterocyclic Rearrangement

Silvestre Buscemi, Gabriella Macaluso, and Nicolò Vivona*

*Dipartimento Chimica Organica, Università digli Studi di Palermo, Viale delle Scienze, 90128 Palermo, Italy

Abstract

The photochemical behaviour of some 3-acetylamino-5-aryl-1,2,4-oxadiazoles in methanol at 254 nm has been investigated. A photoinduced rearrangement to the corresponding 2-acetylaminoquinazolin-4-one derivatives has been pointed out and explained as proceeding through a preliminary iso-heterocyclic photoinduced rearrangement to the corresponding 3-aroylamino-5-methyl-1,2,4-oxadiazoles,followed by a subsequent photoreaction of the latter. Some mechanistic considerations are reported.