Synthesis and chemical properties of 8-aryl-7-acyl-1-6-dimethyl-6-hydroxy-4-cyano-5,6,7,8-tetrahydro-3(2H)-isoquinolinones and isoquinolinethiones

Nitrophenyl-group-containing Heterocycles. Part I. Synthesis, Characterization, Anticancer Activity and Antioxidant Properties of Some New 5,6,7,8-tetrahydroisoquinolines Bearing 3(4)-nitrophenyl Group

“…The presence of tertiary alcoholic group in all compounds was acertained from their 1 H NMR spectra which possess a singlet signal at δ value ranged from 4.56 to 4.89 equivalent to one proton of (OH) group. 1 H NMR spectra of all compounds displayed characteristic signals at certain δ values which are equivalent to the protons of cyclohexene ring and in accordance with those reported before for their analogues [25]. 13 C NMR spectra of compounds 4a, 8b-d, 8f and 9a-e displayed characteristic peaks at certain δ values which are in agreement with their structures.…”

“…Thus, IR spectra of 2a,b showed characteristic absorption bands in the regions 3482-3429 cm -1 for (O-H), 3235-3106 cm -1 for (NH), 2221-2220 cm -1 for (C≡N), and 1710-1708 cm -1 for (C=O, acetyl). 1 H NMR spectra of 2a,b are in agreement with those of their analogues which reported before [25]. IR spectrum of 3 revealed the disappeance of NH whereas its NMR spectra showed the presence of ethyl group.…”

Synthesis of 7-acetyl-8-aryl(hetaryl)- 6-hydroxy-1,6-dimethyl-3-selenoxo-2,3,5,6,7,8-hexahydroiso-quinoline-4-carbonitriles by the condensation of 2,4-diacetyl-3-aryl(hetaryl)- 5-hydroxy-5-methyl-cyclohexanones with cyanoselenoacetamide

“…Unlike the functionally substituted 3-oxo-and 3-thioxo-2,3,5,6,7,8-hexahydroisoquinolines synthesized previously [2], their 3-selenoxo analogs are unknown.…”

“…It has been shown for the first time that the previously unknown 7-acetyl-8-aryl(hetaryl)-6-hydroxy-1,6-dimethyl-3-selenoxo-2,3,5,6,7,8-hexahydroisoquinoline-4-carbonitriles 3a-e are formed on condensing 2,4-diacetyl-3-aryl(hetaryl)-5-hydroxy-5-methylcyclohexanones 1a-e with cyanoselenoacetamide (2) in absolute ethanol in the presence of triethylamine in an atmosphere of argon at 60 o C. The reaction scheme probably includes a stage of forming intermediates 4 which cyclocondense intramolecularly into compounds 3a-e.…”

The Reaction of 5-Amino-3-(cyanomethyl)-1H-pyrazol-4-carbonitrile with beta-Cycloketols

“…However, the heterocyclization reactions of β-cycloketols are not well studied. Thus, the literature describes the preparation of isoquinolines 2 [3][4][5][6][7], indazoles 3 [8][9][10], benzo[c]isoxazoles 4 [9,10], [1,2,4]triazolo [3-b]quinazolines 5 [11] and pyrazolo[3-c]isoquinolines 6 [12] (Scheme 1) by reactions of beta-cycloketols with various 1,2-and 1,3-dinucleophilic agents. Despite the large attention paid to reactions of aminoazoles with 1,3-dielectrophilic agents (see reviews [13,14]), only a few examples of reactions involving β-cycloketols were found in the literature.…”