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Multicomponent condensation of 3-aryl(hetaryl)-2,4-diacetyl-5-hydroxy-5-methylcyclohexanones with 2-cyanoethanethioamide and alkylating agents in the presence of morpholine afforded 3-(alkylsulfanyl)-8-aryl(hetaryl)-7-acetyl-6-hydroxy-1,6-dimethyl-5,6,7,8-tetrahydroisoquinoline-4-carbonitriles, 1-[1-amino-6aryl(hetaryl)-8-hydroxy- 6,7,8,9-tetrahydrothieno[2,3-c]isoquinolin-7-yl]ethanones, and 3,3′-[ethane-1,2-diylbis(sulfanediyl)]bis[7-acetyl-6-hydroxy-1,6-dimethyl-8-(furan-2-yl)-5,6,7,8-tetrahydroisoquinolin-4-carbonitrile].

The synthesis of 1H-pyrazolo[3,4-c]isoquinolin-1-ones was carried out by reacting 3-aryl(heteryl)-2,4-diacetyl-5-hydroxy-5-methylcyclohexanones with 3-amino-1-phenyl-1H-pyrazol-5(4H)-one. The structure of the 7-acetyl-2, 4,6,7,8,9-hexahydro-8-hydroxy-5,8-dimethyl-2-phenyl-6-(fur-2-yl)-1H-pyrazolo[3,4-c]isoquinolin-1-one obtained was proved by X-ray diffraction analysis.On the basis of tetrahydroisoquinoline a series of compounds used in medicine as drugs has been synthesized [1, 2]. Besides, the isoquinoline framework is a part of many alkaloids exhibiting pharmacological effect [3][4][5]. In turn, among the pyrazoloizoquinolines some kinase inhibitors were identified, which were taken as the base to develop drugs for the treatment of osteoarthritis, rheumatoid arthritis and asthma [6]. Therefore, the development of the methods of synthesis and production of new compounds of this class is relevant and promising in terms of finding new biologically active substances.In the present study, we investigated a reaction of 3-aryl(heteryl)-2,4-diacetyl-5-hydroxy-5-methylcyclohexanones (Ia-Ig) with 3-amino-1-phenyl-1H-pyrazol-5H-one (II). We found that at reflux in the presence of sodium ethoxide a formation occurs of new derivatives of the tricyclic system 6-aryl(heteryl)-7-acetyl-2,4, 6,7,8,9-hexahydro-8-hydroxy-5,8-dimethyl-2-phenyl-1H-pyrazolo[3,4-c]isoquinolin-1-ones (IIIa-IIIg), apparently as a result of intramolecular cyclization of intermediates (A).Structure of compounds obtained is confirmed by spectral studies (see Experimental). However, unambiguous choice between the prototropic tautomers III and IV was impossible. Therefore, the structure of 7-acetyl-2,4,6,7,8,9-hexahydro-8-hydroxy-5,8-dimethyl-2-phenyl-6-(fur-2-yl)-1H-pyrazolo[3,4-c]isoquinolin-1-one IIIf was studied by the X-ray diffraction analysis (see the figure and Tables 1, 2).

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SHORT COMMUNICATIONS isoquinolin-1-ones can be synthesized by condensation of 2-acetylcyclohexanones with 3-amino-1-phenyl-1H-pyrazol-5(4H)one [1] or via nucleophilic vinylic substitution (S N Vin) in reactions of 1-[2-(morpholin-4-yl)cyclohexyl]alkanones with the same pyrazolone [2]. The alkylation of pyrazoloisoquinolines containing no functional substituents in the cyclohexane ring with alkyl halides in DMF in the presence of aqueous potassium hydroxide gave the corresponding N 3 -alkyl derivatives [2]. No other examples of alkylation of this heterocyclic system have been reported. 1, R = Ph (a), furan-2-yl (b); 2, PhCH 2 Cl (a), MeI (b); 3, R = Ph, R′ = PhCH 2 (a); R = furan-2-yl, R′ = PhCH 2 (b); R = furan-2-yl, R′ = Me (c).