Applied Chemistry, Vol.2, No.1, 417-420, May, 1998
TMSCI/NaI를 이용한 이중고리 이소옥사졸 유도체의 환원분해반응에 의한 3,4-치환된 이소옥사졸의 합성
Synthesis of 3,4-Disubstituted Isoxazoles by Reductive Cleavage of Bicyclic Isoxazole Derivatives with TMSCI/NaI
Synthetic methodology for 3,4-disubstituted isoxazole derivatives from the reductive cleavages of 4,5-dihydro-7H-pyrano[3,4-c]isoxazoles 1 or 4H,6H-furo[3,4-c]isoxazoles 5 is described. Pyrano[3,4-c]isoxazole 1, upon treatment with TMSCl/NaI in acetonitrile, undergoes selective C-O bond cleavage to furnish a 3,4-disubstituted isoxazole (2, 3, 4) in high yield without damaging the isoxazole ring. Likewise, the treatment of furo[3,4-c]isoxazoles 5 with TMSCl/NaI in acetonitrile results in the formation of a reduced iodide 7 and a hydroxy iodide 8.