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Paper | Regular issue | Vol 41, No. 5, 1995, pp.1051-1070
Published online, 1st January, 1970
DOI: 10.3987/COM-95-7044
Synthesis of Fused 3a,4-Dihydro-5a,H-benzofuro[3,3a-d]isoxazoles

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

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

Abstract

Reaction of 2-isoxazoline-2-oxides (1) with titanium tetrachloride afforded Diels-Alder dimers (3) of 3a,4-dihydro-5a,H-benzofuro[3,3a-d]isoxazoles (2). The stereochemistry of the dimer (3a) was confirmed by X-ray analysis. As an application of the Diels-Alder reaction, several fused 3a,4-dihydro-5a,H-benzofuro[3,3a-d]isoxazoles (5,6, and 7) were synthesized by the reactions of 2 with acetylenic dienophiles.