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Unstable 8-p-tolylsulfonylimino-5,8-dihydroquinolin-5-one was generated by oxidation of the corresponding reduced form in acetic acid; it reacted in situ with hydrogen chloride and sodium p-toluenesulfinate to give the corresponding 6-substituted 5-hydroxy-8-aminoquinolines.There are almost no published data on N-substituted 8-imino-5,8-dihydroquinolin-5-ones. An attempt was made to correlate antimalarial activity of 8-amino-6-methoxyquinolines with their ability to undergo oxidation to 8-imino-6-methoxy-5,8-dihydroquinolin-8-ones [1], though the corresponding quinoid metabolites were not isolated by independent synthesis [2] because of their instability. The only stable compound of this series, 6-(4-methoxyphenylamino)-8-(4-methoxyphenylimino)-5,8-dihydroquinolin-5-one was obtained by treatment of 6-piperidino-5,8-dihydroquinoline-5,8-dione with excess p-methoxyaniline in acetic acid [3].In the preceding communications we reported on the reactivity of 8-p-tolylsulfonylimino-5,8-dihydroquinolin-5-one derivatives. We found that reactions of these compounds with nucleophilic reagents are governed by the tosylimino group rather than by the endocyclic nitrogen atom [4,5]. In the present work we made an attempt to synthesize 8-arylsulfonylimino-5,8-dihydroquinolin-5-ones. The initial model compound, 8-p-tolylsulfonylimino-5,8-dihydroquinolin-5-one (I), and its derivatives were synthesized following the reaction sequence shown in Scheme 1. The reaction of 8-nitroquinoline (II) with hydroxylamine hydrochloride in alcoholic alkali afforded 5-amino-8-nitroquinoline (III). The latter was converted into 5-hydroxy-8-nitroquinoline (IV) by alkaline hydrolysis according to a specially developed procedure. For this purpose, nitro compound IV was reduced to 8-amino-5-hydroxyquinoline dihydrochloride (V) with tin(II) chloride in hydrochloric acid. Compound V was treated with p-toluenesulfonyl chloride in methanol in the presence of 2 equiv of pyridine to obtain 8-p-tolylsulfonylamino-5-hydroxyquinoline hydrochloride (VI). Oxidation of tosyl derivative VI with (diacetoxy-l 3 -iodanyl)benzene in acetic acid in the presence of an equimolar amount of sodium acetate afforded quinone imine I as a dark green solid material which gradually dissolved in the reaction mixture, giving rise to a dark blue solution. We failed to isolate quinone imine I as individual substance. Nevertheless, by treatment of the reaction mixture at the moment of formation of quinone imine I precipitate with hydrochloric acid or sodium p-toluenesulfinate dihydrate we succeeded in isolating new compounds, 6-chloro-5-hydroxy-8-p-tolylsulfonylaminoquinoline hydrochloride (VII) and 5-hydroxy-6-p-tolylsulfonyl-8-p-tolylsulfonylaminoquinoline (VIII), respectively.The presence of a substituent in position 6 of the quinoline ring system was proved as follows. The oxidation of salt VII with (diacetoxy-l 3 -iodanyl)benzene under the same conditions as in the generation of quinone imine I gave unstable 6-chloro-8-p-tolylsulfonylimino-5,8-dihydroquinolin-5-one (IX) w...

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The quality of university management depends on numerous factors, including the consequences it has on the local community. While the consequences have numerous and hardly equitable aspects, this article suggests a synthetic model for the assessment of university management, which considers a full range of existing effects. The research methodology is based on the balanced scorecard concept. Verification, using the available empirical data for comparison of two universities, confirms the model's validity. Thus, the article recommends this model for solving a whole range of university management issues, especially in the interaction of higher education entities with outer and inner communities.

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Existing methods of combating the shadow economy do not always give reliable results. This is particularly true for the illegal use of renewable natural resources. In some parts of the Northwest Pacific basin, illegal, unreported, and unregulated (IUU) fishing has become an issue of growing concern for the sustainability of resource management, ecology, and the social environment. Many factors combine to produce these harmful phenomena. The complex legal rights for shared natural marine resources, the weak capacity of state institutions, and the lack of international cooperation between exporters and importers are all relevant. These factors can be eliminated by supplementing the “traditional” analysis of the shadow economy with new data mined from the media. For the crab harvesting regions of Russia, long-lasting benefits can be achieved through improvements in governance, accountability, and public awareness, or more specifically, through extensive mass media coverage of relevant topics. We argue that in the Russian Pacific, levels of illegal crab harvesting and smuggling correlates closely to the frequency of media references. The results suggest possible applications of mass media analysis: developing additional metrics for the dynamics of shadow economies; and the formulation of effective policy recommendations for sustainable fishing.