S. V. Kol'tsova

Synthesis and Antimicrobial Activity of the Products of Interaction of 3-Aroyl-2,4-dihydro-1h-pyrrolobenzoxazine-1,2,4-triones with Urea and Thiourea

The products of interaction of 3-aroyl-2,4-dihydro-1Hpyrrolo[2,1-c]benzoxazine-1,2,4-triones (I – IV) with water exhibited antimicrobial activity. In this context, it was of interest to study the antimicrobial properties of the products of interaction of pyrrolobenzoxazinetriones I – IV with some other nucleophilic reagents, in particular with urea and thiourea, taking into account the role of these fragments in various biologically active compounds [2]. Boiling 3-aroyl-2,4-dihydro-1H-pyrrolo[2,1-c]benzoxazine-1,2,4-triones (I – IV) with urea or thiourea in acetonitrile or dioxane for 3 – 5 min led to a high yield of 3-[ -(2,5dioxoand 5-oxo-2-thioxo-Z-4-imidazolidinylidene)phenacyl]-2H-1,4-benzoxazin-2-ones (V – XII) (Table 1).

A Comparative Study of the Antimicrobial Activity of Some Quinoxalines, 1,4-Benzoxazines, and Aza-Analogs

It was reported that (Z )-3-phenacylidene-1,2,3,4tetrahydro-2-quinoxalones and (Z )-3-phenacylidene-3,4dihydro-2H-1,4-benzoxazin-2-ones [1, 2] possess antiinflamatory [2, 3], antitumor, and bacteriostatic properties [4]. The purpose of our study was to modify the structure of these compounds by substituting the heteroyl fragment for the aroyl fragment and introducing a heteroatom into the benzene ring of quinoxaline or 1,4-benzoxazine, so as to trace the possible change in activity (in particular, antimicrobial) in the series of such derivatives. For this purpose, we have synthesized a series of compounds including (Z )-3-aroyl(heteroyl)methylene-1,2,3,4-tetrahydro-2-quinoxalones (I, II) [5], (Z )-3-aroyl(heteroyl)-methylene-3,4-dihydro-2H-1,4-benzoxazin-2-ones (III – V) [5], (Z )-2-heteroylmethylene-1,2,3,4-tetrahydropyrido[2, 3-b]pyrazin-2-ones (VI, VII) [6], and (Z )-3-aroyl(heteroyl)methylene-3,4-dihydro2H-pyrido[2, 3-b]-1,4-oxa-zin-2-ones (VIII – IX). The synthesized compounds were tested for antimicrobial activity. Aroyl(heteroyl)pyridooxazinones (VIII – X) were obtained via the interaction of equimolar amounts of the corresponding 4-aryl(heteryl)2,4-dioxobutanoic acids and 2-amino-3-hydroxypyridine. Compounds VIII – X appear as bright-yellow crystalline substances, soluble in ethanol, dioxane, and acetonitrile and insoluble in water (Table 1). The spectroscopic characteristics of the new products agree well with those of the previously reported aroyl(heteroyl)-1,4-banzoxazinones [2, 5]. Indeed, the IR spectra of compounds VIII – X (Table 2) exhibit absorption bands due to the stretching vibrations of ketone carbonyl groups in the region of 1630 – 1640 cm – 1 and ester carbonyl groups at 1770 cm – . The H NMR spectra of com-

Five-Membered 2,3-Dioxo Heterocycles: XLIV. Reaction of 3-Aroyl-1,2,4,5-tetrahydropyrrolo[1,2-a]- quinoxaline-1,2,4-triones with o-Phenylenediamines

The reaction of (Z)-3-phenacylidene-1,2,3,4-tetrahydroquinoxalin-2-ones with oxalyl chloride gives 3-aroyl-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-1,2,4-triones which react with o-phenylenediamine to afford 8-aryl-6,7,9,14,15,16-hexahydroquinoxalino[1,2-a]pyrrolo[2,3-b][1,5]benzodiazepine-6,7,15-triones.

Synthesis and Antiinflammatory Activity of the Products of Interaction of 4-Aroyl-1,2-dihydro-4H-pyrrolo[5,1-c][1,4]benzoxazine-1,2,4-triones with 4-Amino-1,2,4-triazole

Previously we studied the interaction of 4-aroyl-2,4-dihydro-4H-pyrrolo[5,1-c][1,4]benzoxazine-1,2,4-triones and 3-aroyl-1,2,4,5-tetrahydropyrrolo[1,2-a]quinoxaline-1,2,4triones with various nucleophilic reagents [1 – 4] and characterized some of the synthesized compounds with respect to pharmacological activity [3]. To our knowledge, the reactions of hetereno[a]-2,3-dihydro-2,3-pyrrolodiones and their monocyclic analogs with 4-amino-1,2,4-triazole were not studied until now.

Reactions of aroylpyruvic acids withS-methylisothiosemicarbazide hydroiodide and studies of the crystal structures of the reaction products

The reactions ofp-chlorobenzoyl- and benzoylpyruvic acids withS-methylisothiosemicarbazide hydroiodide gave 3-methylthio-6-(p-chlorophenacyl)-2,5-dihydro-1,2,4-triazin-5-one and 6-phenacyl-2,3,4,5-tetrahydro-1,2,4-triazine-3,5,-dione, respectively. The molecular and crystal structures of the compounds synthesized were studied by X-ray diffraction analysis.

Synthesis of N-aroylpyruvoyl- and N-aroylacetyl-hetarylaminonitriles

Abstract5-Aryl-2,3-dihydrofuran-2,3-diones react with five-membered hetarylaminonitriles to give N-aroytpyruvoyl and N-aroylacetyt derivatives of the latter. The reaction of 2,2-dimethyl-6-aryl-1,3dioxin-4-ones with these hetarylaminonitriles leads solety to the N-aroylacetyl derivatives.

Interaction of 5-Aryl-2,3-dihydrofuran-2,3-diones with Functionally Substituted Hydrazides and Diaminoglyoxal Diphenylhydrazone

The reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with cyanoacetylhydrazide, o-(hydrazinocarbonyl)phenylthiourea, and the diphenylhydrazone of diaminoglyoxal leads to the synthesis of the corresponding N-cyanoacetylhydrazides of aroylpyruvic acids, 2-(N-aroylpyruvoylhydrazinocarbonyl)-phenylthioureas, and 5,6-bis(phenylhydrazono)-3-aroylmethylenepiperazin-2-ones. The results of the primary investigation of the biological activity of N-cyanoacetylhydrazides of aroylpyruvic acids are given.