Saturated nitrogen-containing heterocycles

A general method for the synthesis of pyrrolidinyland cycloalkanopyrrolidinylpropionic acids by the oxidation of the corresponding heterocyclic alcohols has been developed. Some of those compounds have been converted into the corresponding methyl esters and pyrrolizidin-3-ones. Preliminary pharmacological tests have shown that the pyrrolizidin-3-ones possess a sedative effect.For Communication III, see [1].Deceased.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 8, pp. 1051–1055, August, 1970.     

Saturated nitrogen-containing heterocycles

The method for the preparation of hydroxyalkyl derivatives of pyrrolidine and cyclo-alkanopyrrolidines developed previously has been improved by the replacement of the Raney nickel catalyst by Raney cobalt or partially deactivated palladized carbon. The synthesis of N-methylpyrrolidinylpropanols and cyclopentano[b]pyrrolidinylpropanols and their esterification with some aromatic acids have been performed.For Communication II, see [3].Translated from Khimiya Geterotsiklicheskikh Soedinii, Vol. 6, No. 6, pp. 787–790, June, 1970.     

Saturated nitrogen-containing heterocycles

Alcohols of the cyclopentanopyrrolidine series were obtained by hydrogenation of furfurylcyclopentylamines. The dependence of the yields of the products of this reaction on the structure of the amine undergoing hydrogenation and on the catalyst used was established.     

Saturated nitrogen-containing heterocycles. 13. Perhydroacridines. Synthesis and stereochemistry

The configurations of the perhydroacridines formed in the catalytic hydroamination of threo-methylenedicyclohexanone and the product of its cyclization — 2-hydroxy-2,3-tetramethylenebicyclo[3.3.1]nonan-9-one — were established by means of the ¹³C NMR spectra and alternative synthesis. It is shown that isomers with cis-anti-cis and cis-syn-cis configurations are formed as a result of the reactions. The results of x-ray diffraction analysis are presented for cis-syn-cis-N-(2-hydroxyethy1)perhydroacridine.See [1] for Communication 12.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1645–1650, December, 1987.     

Saturated nitrogen-containing heterocycles. 16. Catalytic synthesis of N-arylperhydroacridines

Catalytic hydroamination of methylene-2,2-dicyclohexanone in the presence of substituted anilines or nitrobenzenes involves the formation of N-arylperhydroacridines. The stereoisomeric composition and yields of the latter are determined by the nature and position of the substituent in the aromatic ring of the aminating agent. The structure of isomeric N-arylperhydroacridines was established from data of ¹³C NMR spectroscopy and x-ray diffraction analysis.For Communication 15, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1094–1100, August, 1993.     

Saturated nitrogen-containing heterocycles. 18. Catalytic synthesis and formation mechanism of substitutedcis-decahydroquinolines and their isologues

Hydromethylamination of 1,3-diaryl-3-(2-oxocyclohexyl)propan-1-ones produces N-methyl-2,4-diaryldecahydroquinolines with cis-fused hetero- and carbocycles that are stabilized in the A conformation. The reaction involves ^2,3,9,10 intermediates and their subsequent reduction.For No. 17, see [1].N. G. Chernyshevskii, Saratov State University, Saratov 410026, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 929–933, July, 1999.     

Saturated heterocycles. 136 . Synthesis of 2-substituted 2-azapyracridone derivatives

By means of Substitution, addition and condensation on the secondary nitrogen of 9-methyl-1,2,3,4-tetrahydro-2-azapyracridone (6) , twenty new azapyracridones were prepared.     

Saturated nitrogen-containing heterocycles. VIII. Synthesis and properties of some substituted pyrrolidylalkanols

Phenyl-substituted pyrrolidylalkanols were synthesized by hydrogenation of the corresponding furan amines in acidic aqueous solution in the presence of nickel on diatomaceous earth. Terephthalates, carbamates, and other pyrrolidylalkanol derivatives were obtained. The ability of (2-pyrrolidyl)-3-alkanols to form an intramolecular hydrogen bond was studied by IR spectroscopy.See [1] for communication VII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 186–190, February, 1976.     

Saturated nitrogen-containing heterocycles. 11. The synthesis and structural studies of octahydroindolylalkanols

A catalytic synthesis was carried out for 3-(1-R-2-octahydroindolyl)alkanols using nickel promoted by ruthenium, Raney nickel, and Raney cobalt previously treated with acetic acid. An x-ray diffraction structural study of the acid tartrate of 3-(1-methyl-2-octahydroindolyl)-1-propanol gave the absolute configuration and conformational and structural features of the cation and tartrate anion.For Communication 10, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 66–70, January, 1985.     

Macrocycles,derivatives of nitrogen-containing heterocycles 2. Synthesis and electrochemical properties of diindolizinadiquinoxalinacyclooxaalkaphanes

Phenylindolizinylquinoxalinomonopodands, obtained by the reaction of 1-(phenylindolizin-2-yl)quinoxalin-2(1H)-one with corresponding dibromotrioxa- and dibromopentaoxaalkanes, undergo oxidative dehydrocyclization assisted by molecular iodine to yield new redox-active diindolizinadiquinoxalinacyclooxaalkaphanes. Using CVA, the indolizine fragments of the heterocyclophanes in acetonitrile are found to undergo three-step oxidation with transfer of one electron in each step. The first and the third steps are reversible, whereas the second is irreversible. The oxidation at potentials of the first peak leads to the stable radical cations registered by ESR (g = 2.0024, a _2N = 0.26 mT).     

Saturated nitrogen-containing heterocycles V. Synthesis of 5-alkyl-n-(β-hydroxyethyl)-2-pyrrolidones

A number of 5-alkyl-N-(-hydroxyethyl)-2-pyrrolidones were synthesized by the reductive ethanolamination of ethyl esters of -keto carboxylic acids in the presence of Raney nickel.See [1] for communication IV.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 331–332, March, 1972.     

Saturated nitrogen-containing heterocycles. 12. Structural studies of cyclopenta(b)pyrrolidinylalkanols

¹³C NMR spectroscopy and x-ray diffraction structural analysis were used to establish the stereochemistry of 3-[N-methyl-2-cyclopenta(b)pyrrolinyl]-1-propanol and its acetyl derivative. The absolute configuration was determined for 3-[N-methyl-2-cyclopenta(b)pyrrolidinyl]-1-propanol acid tartrate dihydrate and the conformational aspects of its cation and tartrate anion were studied.For Communication 11, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 71–75, January, 1985.     

Saturated nitrogen-containing heterocycles. 15. Catalytic synthesis and isomerization of 9-substituted10-methylperhydroacridines

In the catalytic hydromethylamination of 8-substituted 2-hydroxytricyclo[7.3.1.0^2,7]tridecane-13-ones they are converted into 9-substituted 10-methyl-^9,9a-dodecahydroacridines and 10-methylperhydroacridines with trans,anti,cis- and cis,syn,cis-conformation. The ability of the latter to isomerize into the trans,cis,tans-form has been established.For Communication 14, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 200–204, February, 1992.     

Saturated nitrogen-containing heterocycles. 12. Stereochemical properties of hydroxyalkylpyrrolidines using 13C NMR spectroscopy

The ¹³C NMR spectra of fifteen compounds in a series of alkyl- and arylsubstituted cis-isomers of hydroxyalkylpyrrolidines have been recorded, and they have been fully interpreted on the basis of configurational and conformational assignments.For Communication 11, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1201–1204, September, 1988.     

Synthesis of a number of derivatives of alkaloids and of nitrogen-containing heterocycles and their anticholinesterase activities

N-Methyl- and N-phenylcarbamates based on a number of alkaloids and nitrogen-containing heterocycles have been synthesized, and they have proved to be weak irreversible inhibitors of acetylcholinesterase and butyrylcholinesterase. It has been shown that the choline fragments of the above-mentioned carbamates and their β-methylcholine analogs are reversible inhibitors of both cholinesterases and make a substantial contribution to the anticholinesterase activity. Selective inhibitors of ACE and BuCE have been found among the compounds synthesized.     

Synthesis of a number of derivatives of alkaloids and of nitrogen-containing heterocycles and their anticholinesterase activities

N-Methyl- and N-phenylcarbamates based on a number of alkaloids and nitrogen-containing heterocycles have been synthesized, and they have proved to be weak irreversible inhibitors of acetylcholinesterase and butyrylcholinesterase. It has been shown that the choline fragments of the above-mentioned carbamates and their -methylcholine analogs are reversible inhibitors of both cholinesterases and make a substantial contribution to the anticholinesterase activity. Selective inhibitors of ACE and BuCE have been found among the compounds synthesized.A. S. Sadykov Institute of Bioorganic Chemistry, Academy of Sciences of the Uzbek SSR, Tashkent. Translated from Khimiya Prirodynkh Soedinenii, No. 6, pp. 825–831, November–December, 1988.     

Saturated heterocycles. Part 209. Synthesis of 1-cyclohexyl-substituted isoquinoline derivatives

In contrast with earlier literature data [7], both acrylic esters and acrylonitrile underwent Michael addition to l-methyl-3,4-dihydroisoquinolines 1-4 to yield the diesters 5-9 or the dinitrile 10 , respectively. Compounds 5-10 were converted by Claisen condensation to 1-[(3′-methoxycarbonyl- or 1-[(3′-ethoxycarbonyl-4′-oxo)-l'-cyclohexyl]-3,4-dihydroisoquinoline derivatives 11-16 . Several derivatives of 12 were prepared. The new compounds possess various pharmacological actions.     

Saturated nitrogen-containing heterocycles. 14. Synthesis and three-dimensional structures of n-r-dicyclopenta[b,e]piperidines

The catalytic hydroamination of threo-methylenedicyclopentanone using ammonia, methylamine, and monoethanolamine as the aminating agents proceeds stereospecifically with the formation of N-R-cis-syn-cis-dicyclopenta[b,e]piperidines (R=H, CH₃, CH₂CH₂OH). The structures of the latter were proved by ¹³C NMR spectroscopy. The molecular structure of N-(-hydroxyethyl)cis-syn-cis-dicyclopenta[b,e]piperidinium acid tartrate was investigated by x-ray diffraction analysis, and the absolute configuration of its chiral centers was determined.See [1] for Communication 13.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1094–1099, August, 1988.