Microbiological transformations of 9-amino-1,2,3,4,5,6,7,8-octahydroacridine

Chemistry Faculty, M. V. Lomonosov Moscow State University, Moscow 199899. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 712–713, May, 1994. Original article submitted April 25, 1994     

Synthesis of 1,2,3,4-tetrahydro-4-pyridinones by heterocyclization of β-amino-β-arylacryloyloxiranes

The heterocyclization of -alkyl(phenyl)aminocinnamoyloxiranes and their -bromo derivatives under base-catalysis conditions is a convenient method for the synthesis of 3-hydroxytetrahydro-4-pyridinones.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 347–350, March, 1989.     

Synthesis of 1-aryl-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indoles (1,2,3,4-tetrahydro-β-carbolines) under high pressures

The reactions of aromatic aldehydes with tryptamine (1) in solvents of different polarity were studied. The yields of carbolines in the chosen media decrease with an increase in the donating properties of the aryl substituent, but they markedly increase at a high pressure (5 kbar), especially for compounds with electron-donating aryl groups. The phase transition of dioxane at 5 kbar also sharply increases the yields of the target products.     

Synthesis of halogen derivatives of 9-arylamino-1,2,3,4-tetrahydroacridines

A method has been proposed for obtaining halogen-substituted 9-arylamino-1,2,3,4-tetrahydroacridines from the anilides of the corresponding cyclohexylideneanthranilic acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6,No. 7, pp. 974–976, July, 1970.     

Synthesis of 1,2,3,4-tetrahydroquinolines and 1,2,3,4-tetrahydro- 1,6-naphthyridines by a directed lithiation reaction

N-(tert-butoxycarbonyl)anilines (7), are easily converted in a one pot reaction sequence into the N- (tert-butoxycarbonyl)-1,2,3,4-tetrahydroquinolines (8), by directed ortho lithiation followed by reaction with 1- chloro-3-iodopropane, hence providing a new versatile quinoline ring nucleus synthesis. In an analogous reaction 2-N-(tert-butoxycarbonyl)- and an 2-N-(pivaloylamino) pyridine are converted to 1,2,3,4-tetrahydro-1,6- naphthyridines.     

Synthesis and analysis of 1,2,3,4-tetrahydro-(9H)-pyrido[3,4-b]indole

The synthesis of 1,2,3,4-tetrahydro-(9H)-pyrido[3,4-b]indole derivatives was carried out in one pot, by condensation of tryptamin with cycloalkanones in the presence of a polyphosphate ester as the catalyst in moderate to low yields, the aldol condensation being the main products. Reaction of tryptamine and cyclic ketones was also carried out in two stage through the imine intermediate with protic catalysis giving the tetrahydro-β-carbolines 8–14 , in good yields. 2-Methyl derivatives 15–21 , of the tetrahydro-β-carbolines, were obtained in good yields, using methyl iodide in dimethyl sulphoxide-potassium carbonate.     

Synthesis and transformations of 6-acetyl-1,2,3,4-tetrahydro-2,2,4,7-tetramethylquinoline

By acylation of 1,2,3,4-tetrahydro-2,2,4,7-tetramethylquinoline under the conditions of the Friedel–Crafts reaction its 6-acetyl derivative was obtained, which opens the access to new linearly designed 6-(pyrimidin-4-yl)-1,2,3,4-tetrahydro-2,2,4,7-tetramethylquinolines.     

Synthesis of 10-amino-1,2,3,4-tetrahydrobenzo[b][1,6]-naphthyridines and related derivatives

This paper describes the synthesis of some 10-amino-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridines and of the new 13-amino-6,6a,7,8,9,10-hexahydro-12H-benzo[b]pyrido[1,2-g][1,6]naphthyridines starting from isatins and 4-piperidones or quinolizidin-2-one.     

Facile Synthesis of 7-Amino-1,2,3,4-tetrahydro-β-carboline

Abstract

7-Amino-1,2,3,4-tetrahydro-β-carboline has been prepared by a short efficient synthetic sequence based on a regioselective nitration of a fully protected 1,2,3,4-tetrahydro-β-carboline.     

Synthesis of 1,2,3,4-tetrafluoronaphthalene derivatives

Conclusions A new preparative method has been developed for obtaining 1,2,3,4-tetrafluoronaphthalene derivatives by the reaction of substituted tetrafluorobenzobarrelenes with phenyl azide.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, 1969, No. 1, pp. 144–146, January, 1969.     

Infrared absorption spectra of some derivatives of 1,2,3,4-tetrahydro-Β-carboline

The IR absorption spectra in 3800-1400 cm^–1 region of 1-propyl-, 1-carboxy-, 1-carboxy-1-methyl-, and 1-benzyl-1-carboxy-6-hydroxy-1,-tetrahydro--carbolines, their O-methyl derivatives, and their hydrochlorides are discussed. An assignment of the bands due to the stretching vibrations of NH, NH ₂ ⁺ , OH, COO^–, and COOH groups is proposed. The hypothesis has been put forward that strong intermolecular and intramolecular hydrogen bonds exist in the substances studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 6, pp. 775–778, June, 1970.     

微波辐射下合成3-芳基-9-氨基-1,2,3,4-四氢吖啶-1-酮衍生物

在微波辐射和对甲基苯磺酸的催化作用下, 5-芳基-1,3-环己二酮与邻氨基苯甲腈进行缩合反应, 得到了N-取代的2-氨基苯甲腈衍生物, 在K₂CO₃和Cu₂Cl₂的催化作用下进一步合环, 得到3-芳基-9-氨基-1,2,3,4-四氢吖啶-1-酮衍生物, 用LiAlH₄还原羰基得到3-芳基-9-氨基-1,2,3,4-四氢吖啶-1-醇衍生物. 新合成化合物的结构均经元素分析、红外光谱和核磁共振光谱予以确认.     

Synthesis and acylation of 1,2,3,4-tetrahydroisoquinoline derivatives

1,2,3,4-Tetrahydroisoquinolines were synthesized, and their acylation was studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 780–783, June, 1993.