13053-85-5

Upstream product

• 1091602-84-4 3-acetonyl-5-phenyl-1,2,4-oxadiazole 
• 1072-67-9 5-methylisoxazol-3-ylamine 
• 98-88-4 benzoyl chloride 

Downstream Products

• 94-33-7 C₉H₁₀O₃ 
• 1091602-84-4 3-acetonyl-5-phenyl-1,2,4-oxadiazole 
• 137935-59-2 2-benzoylamino-5-methyloxazole 
• 109300-39-2 1-(5-methyl-3-isoxazolyl)-5-phenyltetrazole 
• 55-21-0 benzamide 
• 109300-33-6 N-(5-Methyl-isoxazol-3-yl)-benzimidoyl chloride 

Relevant academic research and scientific papers

Experimental and DFT studies on competitive heterocyclic rearrangements. 3. A cascade isoxazole-1,2,4-oxadiazole-oxazole rearrangement

(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.

Straightforward transformation of isoxazoles into pyrazoles: renewed and improved

Isoxazoles bearing alkyl or carbamoyl groups were transformed into the corresponding pyrazoles in high yields by the treatment with hydrazine in methanol in the presence of a hydrogenation catalyst, e.g., Raney nickel, at ambient temperature. For the synthesis of N-substituted pyrazoles, hydrogenolysis of isoxazole followed by the treatment with substituted hydrazine was required. 3(5)-Aryl- or acylamido-substituted isoxazoles are less suitable for such transformations.

Synthesis of 1-(5-methylisoxazole-3-yl)-5-aryl-tetrazoles and its pyrolysis

3-Aroylamino-5-methylisoxazoles (2) were obtained by the reaction of 3- amino-5-methylisoxazole (1) with different aroyl chlorides. These amides on reaction with phosphorous pentachloride followed by sodium azide yielded 1- (5-methylisoxazole-3-yl)-5-aryl

HETEROCYCLIOC REARRANGEMENTS - THE REARRANGEMENT OF 3-AROYLAMINOISOXAZOLES INTO 2-AROYLAMINOOXAZOLES

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

Synthesis of Isoxazolyltetrazoles

Isoxazolyltetrazoles 6 and 9 have been synthesized by the reaction of 4-aroylamino- and 3-aroylaminoisoxazoles (4 and 8) with phosphorus pentachloride and azidolysis of the resulting imidoyl chlorides, respectively.The structures of these tetrazoles have