Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Gazzetta Chimica Italiana called Reactions with hydrazoic acid in sulfuric acid solutions. XIX. Formation of oxazoles and isoxazoles, Author is Caronna, Gaetano; Palazzo, Salvatore, which mentions a compound: 271-95-4, SMILESS is C12=CC=CC=C1ON=C2, Molecular C7H5NO, Application In Synthesis of 1,2-Benzisoxazole.
cf. CA 45, 2007b; 52, 15481c. The addition of HN3 to o-hydroxy aldehydes occurred without addition of the entire mol. of HN3. 2,5-HO(O2N)C6H3CHO (5 g.) added to 50 ml. CHCl3 and the yellow solution stratified with 15 ml. concentrated H2SO4 (d. 1.84), treated portionwise with 4.2 g. NaN3 with evolution of N and the mixture kept 12 hrs., the colorless CHCl3 layer decanted and the residue washed by decantation with CHCl3, poured slowly onto ice and the H2O-washed product crystallized (alc., C) gave 5-nitro-1,2-benzisoxazole (I), m. 126-7°, also obtained from the CHCl3 mother liquors to give a final yield of 85%. I hydrolyzed in dilute alkali and the orange red solution acidified with dilute HCl gave 2,5-HO(O2N)C6H3CN, m. 190-4°. The original dilute H2SO4 mother liquor made alk. with Na2CO3 and extracted repeatedly with Et2O, the extract evaporated and the residue crystallized from alc. yielded authentic 2-amino-5-nitrobenzoxazole, m. 288°. 5,2-Cl(OH)C6H3CHO (5 g.) in 30 ml. CHCl3 and 10 ml. concentrated H2SO4 treated portionwise with 4.5 g. HN3 and the mixture worked up as before gave 5-chloro-1,2-benzisoxazole, m. 70°, hydrolyzed to the corresponding 5,2-Cl(O2N)C6H3CN, m. 164-5° (H2O), and 2-amino-5-chlorobenzoxazole, m. 184°, together with a small amount of 5,2-Cl(HO)C6H3CN. 2,3,5-HO(Cl2)C6H2CHO (5 g.) in 30 ml. CHCl3, stratified with 30 ml. concentrated H2SO4 and treated portionwise with 4 g. NaN3 yielded, on working up, 5,7-dichloro-1,2-benzisoxazole, m. 107°, converted by alk. hydrolysis to 2,3,5-HO(Cl2)C6H2CN, m. 139°, and 2-amino-5,7-dichlorobenzoxazole, m. 251°. The average yields of benzisoxazoles from the corresponding aldehydes were about 90%. A probable mechanism for the cyclization was discussed.
This literature about this compound(271-95-4)Application In Synthesis of 1,2-Benzisoxazolehas given us a lot of inspiration, and I hope that the research on this compound(1,2-Benzisoxazole) can be further advanced. Maybe we can get more compounds in a similar way.
Reference:
Highly efficient and robust molecular ruthenium catalysts for water oxidation,
Catalysts | Special Issue : Ruthenium Catalysts – MDPI