Yu. S. Rozhkova

Synthesis of 1-substituted 2-azaspiro[4.5]deca-6,9-dien-8-ones and 2-azaspiro[4.5]deca-1,6,9-trien-8-ones by condensation of 2,6-dimethylphenol with isobutyraldehyde and nitriles

Abstract1-Substituted 3,3,7,9-tetramethyl-2-azaspiro[4.5]deca-6,9-dien-8-ones and 3,3,7,9-tetramethyl-2-azaspiro[4.5]deca-1,6,9-trien-8-ones were synthesized by three-component condensation of 2,6-dimethylphenol with isobutyraldehyde and nitriles in concentrated sulfuric acid.

Five-membered 2,3-dioxo heterocycles: LIII. Reaction of 3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones with substituted 1,3,3-trimethyl-3,4-dihydroisoquinolines. A new approach to 13-aza analogs of steroids

Abstract3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with substituted 1,3,3-trimethyl-3,4-dihydroisoquinolines to give the corresponding 3-aroyl-4-hydroxy-1-(2-hydroxyphenyl)-5′,5′-dimethyl-5′,6′-dihydro-1H-spiro[pyrrole-2,2′-pyrrolo[2,1-a]isoquinoline]-3′,5-diones. 7′,8′-Benzo derivatives of the latter may be regarded as 13-azagonane analogs having a spiro-fused pyrrole ring at C16.

Acylation of the enamino tautomer of 2-azaspiro[4.5]deca-1,6,9-trien-8-ones with 5-arylfuran-2,3-diones. Crystal and molecular structure of (2Z,5Z)-3-Hydroxy-5-(6,9-dimethoxy-3,3-dimethyl-8-oxo-2-azaspiro[4.5]deca-6,9-dien-1-ylidene)-1-phenylpent-2-ene-1,4-dione

Abstract5-Arylfuran-2,3-diones reacted with heterocyclic enamines of the 2-azaspiro[4.5]deca-1,6,9-trien-8-one series to give products of β-CH-acylation of the enamino fragment. The structure of (2Z,5Z)-3-hydroxy-5-(6,9-dimethoxy-3,3-dimethyl-8-oxo-2-azaspiro[4.5]deca-6,9-dien-1-ylidene)-1-phenylpent-2-ene-1,4-dione was proved by X ray analysis.

Synthesis and Biological Activity of 3-Spiro[adamantane-2,3′-isoquinolines]

A series of 3-spiro[adamantane-2,3′-isoquinolines] were synthesized. Their neurotropic activity and cytotoxicity were evaluated. Two compounds with anxiolytic activity were found, one of which showed antitumor activity in vitro.

Five-membered 2,3-dioxoheterocycles: LVIII. Reaction of methyl 1-Aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrol-2-carboxylates with substituted 1-methyl-3,4-dihydroisoquinolines. New approach to the synthesis of steroid 13-azaanalogs

Methyl 1-aryl-3-aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with substituted 1-methyl-3,4-dihydroisoquinolines with the formation of substituted 3-oxo-2,3,5,6-tetra-hydropyrrolo[2,1-a]-isoquinoline-2-spiro-2′-(1-aryl-3-aroyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrroles). A new approach was developed to the synthesis of 13-azagonanes, substituted benzo[f]pyrrolo[2,1-a]isoquinoline-9-spiro-2′-pyrroles.

1-R-3,3-dialkyl-6,7-ethylenedioxy-3,4-dihydroisoquinolines

A three component “one-pot” condensation of 1,2-ethylenedioxybenzene and RCN nitriles with isobutylene oxide, isobutyraldehyde, or cyclohexanecarboxaldehyde in the presence of conc. H2SO4 gives 1-R-3,3-dialkyl-6,7-ethylenedioxy-3,4-dihydroisoquinolines.

Synthesis of 1′-substituted 4′,4′-dimethyl-6′-methoxy-4′H-spiro[cyclohexane-1,3′-isoquinolines]

The reaction of 1-(4-methoxyphenyl)-1-(1-methylcyclohexyl)ethanol with nitriles in concentrated sulfuric acid afforded 1′-substituted 6′-methoxy-4′,4′-dimethyl-4′H-spiro[cyclohexane-1,3′-isoquinolines] as a result of consecutive Wagner-Meerwein rearrangement and Ritter reaction.

Synthesis of 4′H-spiro[adamantane-2,3′-isoquinoline] derivatives

Syntheses of adamantane derivatives with various nitrogen-containing heterocyclic fragments, such as pyrrolidine [1, 2], diaziridine [3], piperidine, morpholine [4, 5], and perhydroazepine [5], have been reported. Introduction of an adamantane fragment into molecules of analogous biologically active heterocycles is known to affect their pharmacological properties, giving rise to antiviral, antitumor, neurotropic, and other kinds of biological activity.

Synthesis of New 1,2,3,4-Tetrahydroisoquinoline Derivatives. 2-(2,3,3-Trimethyl-1,2,3,4-tetrahydroisoquinolin-1-yl)anilines

A four-step procedure has been developed for the synthesis of new 2-(2,3,3-trimethyl-1,2,3,4-tetrahydroisoquinolin-1-yl)anilines by acylation of 2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)anilines at the amino group with isobutyryl chloride, reduction of the endocyclic C=N bond in N-[2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)phenyl]isobutyramides, N-alkylation of N-[2-(3,3-dimethyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl]isobutyramides to N-[2-(2,3,3-trimethyl-1,2,3,4-tetrahydroisoquinolin-1-yl)phenyl]isobutyramides, and acid hydrolysis of the latter.

Regioselective synthesis of 1-substituted 6-methoxy-3,3,4,4-tetramethyl-3,4-dihydroisoquinolines via Ritter reaction

Abstract2-(4-Methoxyphenyl)-3,3-dimethylbutan-2-ol and nitriles undergo the Ritter reaction in concentrated sulfuric acid to give 1-R-6-methoxy-3,3,4,4-tetramethyl-3,4-dihydroisoquinolines.