Dibenzodiazepines in reactions of 2-acetyldimedone with 3,4-diaminobenzophenone

Authors

  • А. Я. Страков Riga Technical University, Riga LV-1658
  • M. В. Петрова Riga Technical University, Riga LV-1658
  • Н. H. Тонких Riga Technical University, Riga LV-1658
  • А. И. Гурковский Riga Technical University, Riga LV-1658
  • Ю. Пoпeлиc Latvian Institute of Organic Synthesis, Riga LV-1006
  • Г. П. Крейшман University of Cincinnati, Ohio
  • C. В. Беляков Latvian Institute of Organic Synthesis, Riga LV-1006

Abstract

The reactions of 2-acetyldimedone and 2-acetyl-3-methoxy-5,5-dimethylcyclohex-2-en-1-one with 3,4-diaminobenzophenone produce 2-[1-(2-amino-5-benzoylphenyl)amino]ethylidene-5,5-dimethyl-1,3-cyclohexanedioneand 2-acetyl-3-(2-amino-5-benzoylphenyl)amino-5,5-dimethylcyclohex-2-en-1-one, which are cyclized by the action of hydrochloric acid, yielding the respective hydrochlorides of 8-benzoyl- and 7-benzoyl-3,3,11-trimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepin-2-ones. Hydrolytic cleavage of the 8-benzoyl derivative leads to 2-acetyl-3-(2-amino-4-benzoylphenyl)amino-5,5-dimethylcyclohex-2-en-1-one. A similar cleavage to form 2-acetyl-3-(2-aminophenyl)amino-5,5-dimethylcyclohex-2-en-1-one is observed for the known hydrochloride of 3,3,11-trimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepin-2-one. The structures of the products were confirmed by PMR spectra and X-ray diffraction data.

How to Cite
Strakov, A. Y.; Petrova, M. V.; Tonkikh, N. N.; Gurkovskii, A. I.; Popelis, Yu.; Kreishman, G. P.; Belyakov. S. V. Chem. Heterocycl. Compd. 1997, 33, 321. [Khim. Geterotsikl. Soedin. 1997, 379.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02253113

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Published

2025-10-27

Issue

No. 3 (1997)

Section

Original Papers