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Paper | Special issue | Vol 56, No. 1-2, 2002, pp.291-303
Published online, 1st January, 1970
DOI: 10.3987/COM-01-S(K)38
Qinolone Analogues 4. Synthesis ofÅ@1-Methyl-3-trifluoromethylpyridazino[3,4-b]quinoxalin-4(1H)-ones

Yoshihisa Kurasawa,* Izumi Matsuzaki, Waka Satoh, Yoshihisa Okamoto, and Ho Sik Kim

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


The reaction of the quinoxaline N-oxides (7a,b) with 4,4,4-tri-fluoroacetoacetate gave the 1,5-dihydro-3-trifluoromethylpyridazino[3,4-b]quino-xaline-4-carboxylates (15a,b), whose oxidation with nitrous acid afforded the 1,4-dihydro-4-hydroxy-3-trifluoromethylpyridazino[3,4-b]quinoxaline-4-carboxylates (16a,b), respectively. The reaction of compounds (16a,b) with 1,8-diazabi-cyclo[5.4.0]-7-undecene (DBU) provided the 1,5-dihydro-3-trifluoromethylpyridazino[3,4-b]quinoxalin-4-ols (17a,b), whose oxidation with sodium bromate produced the 1-methyl-3-trifluoromethylpyridazino[3,4-b]quinoxalin-4(1H)-ones (6a,b), respectively.