Experimental and DFT Studies on Competitive Heterocyclic Rearrangements. A Cascade Isoxazole-1,2,4-Oxadiazole-Oxazole Rearrangement

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Abstract

The thermal rearrangements of 3-acylamino-5-methylisoxazoles 1 have been investigated under basicand neutral conditions and interpreted with the support of computational data. The density functionaltheory (DFT) study on the competitive routes available for the base-catalyzed thermal rearrangement ofisoxazoles 1 showed that the Boulton-Katritzky (BK) rearrangement, producing the less stable 3-acetonyl-1,2,4-oxadiazoles 5, is a much more favored process than either the migration-nucleophilic attack-cyclization(MNAC) or the ring contraction-ring expansion (RCRE). In turn, an increase in reaction temperaturewill promote the MNAC of oxadiazoles 5, producing the more stable 2-acylaminooxazoles 8. The thermalrearrangement of 3-acylaminoisoxazoles 1 into oxazoles 8 can therefore be interpreted in terms of acascade BK-MNAC rearrangement involving 3-acetonyl-1,2,4-oxadiazoles 5 as ancillary intermediates.
Lingua originaleEnglish
pagine (da-a)351-358
Numero di pagine8
RivistaJournal of Organic Chemistry
Volume74
Stato di pubblicazionePublished - 2009

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

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