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Communication | Regular issue | Vol 23, No. 1, 1985, pp.65-70
Published online, 1st January, 1970
DOI: 10.3987/R-1985-01-0065
Ring Transformation of a 3-Quinoxalinyl-1,5-benzodiazepine into Novel 3-(Benzimidazol-2-ylmethylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline. Convenient Synthesis of Novel 2,3-Fused Quinoxalines

Yoshihisa Kurasawa,* Sayuri Shimabukuro, Yoshihisa Okamoto, and Atsushi Takada

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

Abstract

Ring transformation of the 3-quinoxalinyl-1,5-benzodiazepine hydrochloride (2) gave novel 3-(benzimidazol-2-yl-methylene)-2-oxo-1,2,3,4-tetrahydroquinoxaline hydrochloride (3a), whose treatment with 5% NaOH afforded the free base (4a). Compounds 3a and 4a were converted into the 2,3-fused quinoxalines (6 and 8) via the oxime (5) and ketone (7), respectively.