58455-03-1Relevant academic research and scientific papers
Experimental and DFT studies on competitive heterocyclic rearrangements. Part 2: A one-atom side-chain versus the classic three-atom side-chain (Boulton-Katritzky) ring rearrangement of 3-acylamino-1,2,4-oxadiazoles
Pace, Andrea,Pibiri, Ivana,Piccionello, Antonio Palumbo,Buscemi, Silvestre,Vivona, Nicolo,Barone, Giampaolo
, p. 7656 - 7666 (2008/02/12)
(Chemical Equation Presented) The experimental investigation of the base-catalyzed rearrangements of 3-acylamino-1,2,4-oxadiazoles evidenced a new reaction pathway which competes with the well-known ring-degenerate Boulton-Katritzky rearrangement (BKR). T
Studies on azole-to-azole interconversions. Substituent effects on the ring-degenerate equilibration between 3-aroylamino-5-methyl-1,2,4-oxadiazoles and 3-acetylamino-5-aryl-1,2,4-oxadiazoles
Buscemi,Buscemi, Silvestre,Frenna,Frenna, Vincenzo,Vivona,Vivona, Nicolo,Petrillo,Petrillo, Giovanni,Spinelli,Spinelli, Domenico
, p. 5133 - 5142 (2007/10/02)
The title reaction has been studied both in CD3OD and (t)BuOK/CD3OD by means of 1H NMR measurements. The equilibrium composition and the effect exerted thereon by X-substituents in the aryl moiety have been found to be quite different whether neutral or anionic forms are involved. In the first case the effect of X is meager and 3-acetylamino-1,2,4-oxadiazoles are more stable than the 3-aroylamino-5-methyl isomers. Vice-versa, when anions are involved the substituent effect is remarkable and the equilibrium can be, for strongly electron-withdrawing X-groups, even largely shifted towards the anions of the 3-aroylamino-5-methyl-1,2,4-oxadiazoles.
