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Synthesis 1987; 1987(4): 379-381
DOI: 10.1055/s-1987-27951
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Novel Ring Transformations of 4-Acylamino- and 4-Dimethylaminomethyleneamino-1H-1,5-benzodiazepine-3-carbonitriles to Pyrimidine-5-carbonitriles

Kaname Takagi* , Tomoji Aotsuka, Hikari Morita, Yoshihisa Okamoto
  • *Central Research Laboratories, Zeria Pharmaceutical Co., Konanmachi, Osato-gun, Saitama 360-01, Japan
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Publikationsdatum:
20. August 2002 (online)

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Reaction of 4-acylamino-1H-1,5-benzodiazepine-3-carbonitriles 1 with methylamine gave 2-alkyl-4-(o-aminophenylimino)-1-methyl-1,4-dihydropyrimidine-5-carbonitriles 4. 4-Dimethylaminomethyleneamino-1H-1,5-benzodiazepine-3-carbonitrile 2 also underwent analogous ring transformation with methylamine and ammonia to give pyrimidine-5-carbonitriles 9 and 10. The pyrimidines so formed were converted to benzimidazoles 6 and 12.