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Paper | Regular issue | Vol 29, No. 10, 1989, pp.2007-2021
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5102
Synthesis of 5-(4-Pyrazolyl and 4-Isoxazolyl)-1,3-dihydro-2H-1,4-benzodiazepin-2-ones

Takushi Kurihara,* Jun Sasaki, Kazunori Santo, Yutaka Nakamura, Ryuji Yoneda, and Shinya Harusawa

*Faculty of Pharmaceutical Science, Osaka University of Pharmaceutical Sciences, 4-20-1 Nasahara, Takatsuki, Osaka 569-1094, Japan

Abstract

Reaction of 3-(4-pyrazolyl)anthranil (5) with phenylzinc chloride in the presence of nickel acetylacetonate gave 4-(2-anilinobenzoyl) pyrazole (6). 3-(4-Isoxazolyl)anthranil (11) gave a mixture of 4-(2-anilinobenzoyl)isoxazole (12) and 1-phenyl-4-quinolone (16). The compounds 6 and 12 were readily transformed to the azidoacetanilides (9 and 15), which were cyclized to 1,4-benzodiazepin-2-ones (10 and 19), respectively, via aza-wittig reaction at room temperature. Treatment of azido derivative (25) with triphenyl phosphine gave the phosphinimine (26), which was eventually cyclized to the 1,4-benzodiazepine (27) in refluxing toluene. In contrast, the phosphinimine (41) prepared from 4-(2-azidoacetamido-3-theonyl)isoxazole (40) failed to cyclize to the condensed thieno-1,4-diazepine (42).