137935-59-2Relevant academic research and scientific papers
Experimental and DFT studies on competitive heterocyclic rearrangements. 3. A cascade isoxazole-1,2,4-oxadiazole-oxazole rearrangement
Pace, Andrea,Pierro, Paola,Buscemi, Silvestre,Vivona, Nicolò,Barone, Giampaolo
experimental part, p. 351 - 358 (2009/04/11)
(Figure Presented) The thermal rearrangements of 3-acylamino-5- methylisoxazoles 1 have been investigated under basic and neutral conditions and interpreted with the support of computational data. The density functional theory (DFT) study on the competitive routes available for the base-catalyzed thermal rearrangement of isoxazoles 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 temperature will promote the MNAC of oxadiazoles 5, producing the more stable 2-acylaminooxazoles 8. The thermal rearrangement of 3-acylaminoisoxazoles 1 into oxazoles 8 can therefore be interpreted in terms of a cascade BK-MNAC rearrangement involving 3-acetonyl-1,2,4-oxadiazoles 5 as ancillary intermediates.
HETEROCYCLIOC REARRANGEMENTS - THE REARRANGEMENT OF 3-AROYLAMINOISOXAZOLES INTO 2-AROYLAMINOOXAZOLES
Buscemi, Silvestre,Frenna, Vincenzo,Vivona, Nicolo
, p. 1765 - 1772 (2007/10/02)
When treated with t-BuOK in DMF at 110-120 deg C, 3-aroylamino-5-methylisoxazoles gave good yields of 2-aroylamino-5-methyloxazoles as the ring rearrangement products.The same isoxazole to oxazole ring isomerization has been also observed in a photoinduce
