5,6-Dihydro-4H-imidazo[4,5,1-i,j]quinoline derivatives

The oxidation of 2-hydroxymethyl and 2-methyl derivatives of 5,6-dihydro-4H-imidazo[4,5,1-i,j] quinoline with active manganese dioxide and selenium dioxide gave 2-formyl derivatives of this heterocycle. Some transformations of these compounds are realized.See [1] for communication I.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 967–969, July, 1971.     

5,6-Dihydro-4h-imidazole[4,5,1-i,j]quinoline derivatives

2-Alkyl(dialkyl)amino derivatives of I and their respective cyclic ammonium salts were obtained by reaction of the 2-chloro derivative of 5,6-dihydro-4H-imidazole [4,5,1-i,j ]quinoline (I) and its methiodide with amines. The eycloammonium salt was converted into 2-amino(alkylimino)-l,2-dihydro derivatives of 5. Methoxy- and methyl-substituted I readily formed 2-amino derivatives by reaction with sodium amide. Comparison of the UV spectra of the 2-amino derivative of I and its fixed tautomeric form indicates that the 2-amino derivative of I exists primarily in the amino form in dioxane and CC14.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1410–1413, October, 1970.     

5,6-Dihydro-4H-imidazo[4,5,1-i,j]quinoline derivatives

9-Substituted 5,6-dihydro-4H-imidazo[4,5,1-i,j]quinolines were synthesized and aminated by the action of sodium amide and hydroxylated by fusing with potassium hydroxide. The mononitro and dinitro compounds of some 5,6-dihydro-4H-imidazo[4,5,1-i,j]quinoline deivatives and the corresponding amino and diamino compounds were obtained. The latter react with nitric or formic acids to form a new heterocyclic ring.See [1] for communication II.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 242–246, February, 1972.     

Some 5,6-dihydro-4H-pyrrolo[3,2,1-i,j]quinolines

On the basis of structural features which relate 5,6-dihydro-4H-pyrrolo[3,2,1-i,j]quinolines to indoles, several representative groups of derivatives were synthesized.     

Studies of imidazo[4, 5-f]quinoline

The UV absorption spectra of imidazo[4, 5-f]quinoline and its quaternary salts were examined. The causes of the development of luminescence in solutions of the quaternary salts of imidazo[4, 5-f]quinoline were elucidated.For part I, see [6].     

Transformations of imidazo[4, 5-f]quinoline

Treatment of imidazo[4, 5-f]quinoline and some of its 3-substitmion products with methyl halides and methyl benzenesulfonate gives as the main reaction products N-methylimidazoquinolinium salts, which can also be synthesized from 5, 6-dimainoquinolines. Methylation at the N atom of the imidazole ring is only a side reaction. Treatment with trimethylphenylammonium hydroxide introduces a methyl radical into the NH group of imidazoquinoline, giving a mixture of 1-and 3-substitution products.     

Synthesis of 4-oxo-4H-quino[2,3,4-i,j][1,4]-benoxazine-5-carboxylic acid derivatives

The synthesis and antibacterial activity of 1-substituted amino-2-fluoro-4-oxo-4H-quino[2,3,4-i,j][1,4]benox-azine-5-carboxylic acid derivatives is described. Key steps in the synthesis include carbon homologation and two intramolecular nucleophilic displacement cyclization reactions to generate the 4-oxo-4H-quino[2,3,4-i,j]-[1,4]benoxazine-5-carboxylic acid nucleus.     

Fluoro-containing Heterocycles: VI. New Derivatives of 1,3,4-Thiadiazino[6,5,4-i,j]quinoline

A series of new tricyclic fluoroquinolones was prepared by replacing fluorine atoms in derivatives of 2-R-8-Y-7-oxo-9,10-difluoro-7H-1,3,4-thiadiazino[6,5,4-i,j]quinoline-6-carboxylic acids. In acids and esters containing a hydrogen atom in position 8 occurred replacement of F¹⁰ by amine rests, and in compounds with a fluorine in position 8 was substituted either F⁸or F¹⁰ and F⁸depending on the amine character.     

The syntheses of 4b,5a-dihydrodibenz[3,4:5,6]anthra[1,2-b]oxirene and 4b,5a-dihydro-5H-dibenz[3,4:5,6]anthra[1,2-b]azirine

The syntheses of the K-oxide and K-imine derivatives of dibenz[a,j]anthracene ( 1 ) are described. The parent hydrocarbon 1 that was obtained as a side product in the Elbs pyrolysis of (2-methyl-1-naphthyl)-1′-naphthylmethanone ( 10 ) was oxidized to 3-(2-formylphenyl)-3-phenanthrenecarboxaldehyde ( 3 ). Treatment of the dialdehyde with tris(dimethylamino)phosphine gave 4b,5a-dihydrodibenz[3,4:5,6]anthra[1,2-b]oxirene ( 4 ). Reaction of the oxirane with sodium azide followed by triethyl phosphite cyclization of the mixture of trans azido-alcohols so formed, yielded mainly 4b,5a-dihydrodibenz[3,4:5,6]anthra[1,2-b]azirine ( 5 ).     

Synthesis of as-triazino[5,6-b]quinoline,a new heterocyclic ring system

The first representatives of a new ring system, 3-oxo-2,3,4,10-tetrahydro-as-triazino[5,6-b]quinoline and some of its derivatives were synthesized by cyclization of the appropriate (2-aminobenzyl)-triazines. These substances are in equilibrium with the tautomer 1,2,3,4-tetrahydro form.     

Kinetic resolution of alcohols using a 1,2-dihydroimidazo[1,2-a]quinoline enantioselective acylation catalyst

A new enantioselective acylation catalyst (Cl-PIQ), designed to provide enhanced pi-stacking with benzylic and cinnamyl alcohol substrates, was found to give considerably increased reaction rates and selectivities compared with the first-generation catalyst CF(3)-PIP. [reaction: see text]     

One-pot multicomponent synthesis of some 5,6-dihydro-benzo[h]quinoline derivatives

5,6-Dihydrobenzo[h]quinoline derivatives 4a–f and 5a–c were prepared via condensation of the corresponding arylidenes 2, with 1-tetralone in the presence of ammonium acetate and sodium methoxide, respectively, following thermal, microwave and ultrasound methodologies. The yields of 4a–f were moderate when the latter two methodologies used, but the products were pure. Ultrasound and microwave irradiation methods were also used in the synthesis of 4-aryl-3-cyano-1,2,5,6-tetrahydro-benzo[h]quinoline-2-ones (6a–e) and its analogues 7a,b. The majority of compounds 4–7 were synthesized via one-pot multicomponent reactions of aldehydes, active cyanomethylene compounds, 1-tetralone and ammonium acetate. Attempts to cyclocondensation of the aminocyano derivative 4a,d with acetic anhydride in presence of conc. H₂SO₄ failed; instead the acetylamino derivative 8 was isolated. On the other hand, refluxing of 4d with formamide in DMF led to the formation of dihydrobenzo-pyrimidoquinoline 9 giving good yield. All prepared condensates were structurally elucidated by various spectroscopic methods. Screening of the potential cytotoxicity for compounds 4a–f on five cell lines, namely: colorectal carcinoma (HCT-116), Hepatocellular carcinoma (HEPG2), Human breast adenocarcinoma (MCF7), Cervix adenocarcinoma (HELA) and Glioblastoma (U251), did not show any cytotoxic activity.     

Synthesis of 5,6-dihydro-4H-pyrrolo[1, 2-a] [1,4]benzodiazepines

The title compounds are. Prepared by the reaction of carbonyl compounds with 1-(2′-amino-methylphenyl)pyrrole hydrochloride.     

Synthesis of 4-methyl-1H-imidazo[4,5-c]quinoline

A four-step synthesis of 4-methyl-1H-imidazo[4,5-c]quinoline from 2-methyl-3-nitro-4-oxo-1,4-dihydroquinoline is developed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 231–232, February, 1989.