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Paper | Regular issue | Vol 27, No. 2, 1988, pp.423-435
Published online, 1st January, 1970
DOI: 10.3987/COM-87-4382
Studies on the Chemical Tranformations of Rotenoids. III. Ring Conversations of Methyl Rotenononate and β-Rotenonone

Jinsaku Sakakibara,* Shin-ichi Nagai, Teppei Akiyama, Taisei Ueda, Noriichi Oda, and Kiyoshi Kidouchi

*Faculty of Pharmaceutical Sciences, Nagoya City University, Tanabe-dori, Mizuho-ku, Nagoya 467-8603, Japan


Ring conversions of methyl rotenononate (2b) and β-rotenonone (3) into rotenonone (1) or 4H-furo [2,3-h] [1] benzopyrans (5a-b) were investigated. The Beckmann rearrangement of 2b oxime (6) in PPA provided methyl 3-(benzofuran-5-y1)carbonylamino-(9). 3-(benzofuran-5-yl)aminocarbonyl- 2-benzofurancarbccxylate (10) and furo [2,3-g] benzoxazole (11), whereas 3 oxime (12) gave furo [2,3-g] benzoxazole (13) as a single product. Compound 2b-underwent ring closure with hydrazines to provide benzofuro-[2,3-d]pyridazin-4(3H)-ones (14a-e).