1,4-Benzodiazepines and their cyclic homologs and analogs

5-Difluoromethylsulfonyl-2-aminobenzophenone was synthesized by condensation of p-difluoromethylsulfonylaniline with benzoyl chloride. 5-Difluoromethoxy- and 5-difluoromethylthio-2-aminobenzophenones were obtained by condensation of phenylacetonitrile with the appropriate p-substituted nitrobenzenes and subsequent reduction of the resulting anthranils. 7-Difluoromethoxy-, 7-difluoromethylthio-, and 7-difluoromethylsulfonyl-5-phenyl-1,2-dihydro-3H-1,4-benzodiazepin-2-ones were obtained by the successive action of bromoacetyl bromide and ammonia on the 2-aminobenzophenone derivatives or by reaction of 2-aminobenzophenones with aminoacetyl chloride hydrochloride. The structure of the 1,4-benzodiazepines was confirmed by a study of the UV, IR, PMR, and mass spectra.     

1,4-Benzodiazepines and their cyclic homologs and analogs

A new method, consisting in the reaction of o-aminobenzophenones with -chloropropionyl chloride and subsequent treatment of the resulting 2-(-chloropropionylamino)benzophenones with ammonia, is proposed for the synthesis of 1,2,3,4-tetrahydro-1,5-benzodiazocin-2-ones.Communications I–VII were published under the title 1,4-Benzodiazepines and Their Derivatives. See [1] for communication VII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1705–1706, December, 1972.     

2-Quinazolinones and their cyclic homologs (review)

Methods for the synthesis of 2-quinazolinones, 1,2-dihydro-3H-1,4-benzodiazepin-2-ones, 1,2,3,4-tetrahydro-1,5-benzodiazocin-2-ones, and 1,2,3,4-tetrahydro-5H-1,6-benzodiazonin-2-ones are examined along with the peculiarities of their structure, their tautomerism, their chemical properties, and their biological activity.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 723–738, June, 1979.     

4,5-dihydro-6h-pyrrolo[1,2,3-d,e]quinoxalin-5-ones

The synthesis of 1-R¹-2-R²-8-R³-4,5-dihydro-6H-pyrrolo[1,2,3-d,e]quinoxalin-5-one derivatives (where R¹ = CH₃, C₂H₅; R² = CH₃, COOC₂H₅; R³ = H, CH₃, C₂H₅O, Cl, Br) is described. The physicochemical properties of these derivatives were also studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 839–841, June, 1979.     

Mass spectra of trisubstituted 1,2,3,4-tetrahydro-1,5-benzodiazocin-2-ones

The mass spectra of 1,5-benzodiazocin-2-ones are characterized by multiline character due to the large number of pathways of fragmentation of the molecular ions. In a number of cases the same signal in the high m/e region corresponds to ions with different compositions. The principal fragmentation pathways were determined by high-resolution mass spectrometry. The possible structures of the fragment ions and the mechanisms of their formation are discussed. The mass spectra of model compounds were also investigated for this purpose.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 529–536, April, 1977.     

Macroheterocycles. 7. Synthesis and extraction capacity of some dibenzo-18-crown-6-derivatives

Derivatives that contain vinyl, formyl, acetyl, carboxy, carbethoxy, -carboxyvinyl, or -carbethoxyvinyl groups in the benzene rings were synthesized from dibenzo-18-crown-6. The ability of the synthesized crown ethers to extract picrates of alkali metals from the aqueous phase to the chloroform phase was investigated.See [1] for Communication 6.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 599–603, May, 1981.     

1,4-Benzodlazepines and their cyclic homologs and analogs

A new heterocyclic system of the dumbbell type — 1-[γ-(10-phenothiazinyl)propyl]-1,2-dihydro-3H-1, 4-benzodiazepin-2-one — was synthesized; nine compounds of this type, which have the properties of minor tranquilizers, were synthesized.     

Stereochemistry of heterocycles

A number of previously undescribed alkyl-1,3,2-dioxaborinanes were synthesized by condensation of substituted 1,3-diols with alkylboron dichlorides or dibutyl isopropylborate. It was shown by PMR spectroscopy that the 2,5-dialkyl-1,3,2-dioxaborinane molecules are conformationally homogeneous and do not contain an axial substituent in the 5 position, whereas the 2-isopropyl-5,5-dimethyl-1,3,2-dioxaborinane molecules exist in a state of rapid ring inversion, and introduction of methyl substituents in the 4, 4, and 6 positions of the 1,3,2-dioxaborinane ring leads to distortion of the ring conformation and conformational heterogeneity of the investigated sample. The observed regularities are explained from the position of intensive oxygen-boron electron exchange in the heteroring. It is concluded that the 2,5-dialkyl-1,3,2-dioxaborinane molecules have primarily a conformation with a semiplanar form.See [1] for communication XLVIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp, 26–30, January, 1978