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Paper | Special issue | Vol 42, No. 1, 1996, pp.289-304
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S26
Synthesis of Novel Heterocycle-fused Furo[3,4-d]isoxazoles via Ring Transformation of 2-Isoxazoline-2-oxides by Lewis Acid

Kazuho Harada, Eisuke Kaji, Kuniaki Sasaki, and Shonosuke Zen

*School of Pharmaceutical Sciences, Kitasato University, Shirokane, Minato-ku, Tokyo 108-8641, Japan


Reaction of five-membered heterocycle-substituted 2-isoxazoline-2-oxides (2, 3, and 4) with titanium tetrachloride afforded novel heterocycle-fused furo[3,4-d]isoxazoles (5, 6 and 7), respectively. This transformation was applied to indole-substituted 2-isoxazoline-2-oxide (8) to give the corresponding fused furo[3,4-d]isoxazole (9) and indolo[2,3-b]-1-pyrroline-1-oxide (10).