Hydrogenated azolo- and azinopyridines based on 1,5-diketones

Compounds that contain a hydrogenated azolopyridine structure are formed in the reaction of various types of 1,5-diketones with ethanolamine, o-aminophenol, o-phenylenediamine, and aroylhydrazines; compounds that include a hydrogenated azinopyridine structure were obtained by the reaction of diketones with 3-aminopropanol and anthranilic acid. The hydrocyanation and oxidation of the compounds obtained were studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 240–245, February, 1979.     

Synthetic Amebicides. VIII. 7,7′-[Iminobis(alkyleneimino) [bis[benz[c] acridines] and Congeneric 9-Aminoacridines, 12-Aminobenz[a] acridines, [2-Aminobenz[b] acridines,and 4-Aminoquinolines

Thirty-five 7,7′-(iminodialkylenediimino))bis[benz[c]acridines] (VII), 7,7′-(alkylene- and phenylenediimino)bis[benz[c]acridines] (VIII and IXa-c), [iminobis(alkyleneimino)]bis[acridines, benz[a]acridines, benz[b]acridines, and quinolines] (X, Xla-c, XII, XIII, and XIVa-c), and [alkylenebis(iminoalkyleneimino)]bis[acridines, benz[c]acridines, and quinolincs] (XVI, XVII, XVIIIa and b, and XIXa-c) were synthesized by the condensation of one equivalent of the appropriate alkylenediamine with two equivalents of the requisite chloroheterocycle in phenol. Many of the bis(aminoheterocyclic) compounds are highly active against Entamoeba histolytica in vitro and in experimental animals.     

Organophosphorus compounds based on 1,4- and 1,5-diketones

The phosphorylation reactions of 1,4- and 1,5-diketones with dimethyl phosphites, hypophosphorous acid and its esters, and phosphines are discussed. The reactions lead usually to the formation of cyclic compounds. Dedicated to the memory of Academician M. I. Kabachnik on his 90th birthday. Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1905–1910, October, 1998.     

Chemistry of 1,5-diketones: I. Halogenation of aryl-substituted pent-2-ene-1,5-diones,pentane-1,5-diones,and their fused analogs

Halogenation of 3-(4-methoxyphenyl)-1,5-diphenylpent-2-ene-1,5-dione, 3-(4-methoxyphenyl)-1,5-diphenylpentane-1,5-dione, and 2-[1-(4-methoxyphenyl)-3-oxo-3-phenylpropyl)-1,2,3,4-tetrahydroaphthalen-one with bromine, chlorine, and dichloro(phenyl)-λ³-iodane leads to formation of the corresponding monobromo-, dichloro-, or trichloro-substituted 1,5-diketones, depending on the conditions. Halogenation of the aliphatic chain and methoxyphenyl substituent can be accompanied by heterocyclization to give pyrylium salts.     

Synthesis and characterization of oxadisilole-fused acridines,dioxatrisilole-fused acridines and benzo[b]acridines

Oxadisilole-fused acridines, dioxatrisilole-fused acridines and benzo[b]acridines were synthesized through nucleophilic additions and aromatization reactions of arynes with 2-aminoaryl ketones or 2-aminoaryl aldehydes in good yields at room temperature. The photophysical, redox and thermal properties of these compounds were characterized. These compounds show potential applications as strong deep-blue or green emitters for OLED because of high fluorescence quantum yields and good thermal stabilities.     

Synthesis of substituted 1,4-diazepino[5,6,7-kl]acridines and imidazo[4,5,1-de][1,4]diazepino[5,6,7-mn]acridines

The synthesis of some substituted ll-methoxy-7-nitro-4H,8H-2,3-dihydro-1,4-diazepino[5,6,7-kl]acridines 4 with more diversified chains at position 4 is described. A convenient method for transformation of these compounds into the corresponding 4-substituted 12-methoxy-4H-2,3-dihydroimidazo[4,5,1-de][1,4]diazepino-[5,6,7-mn]acridine (5) is reported.     

Synthesis and crystal structure of piperidinium 2-aryl[1,2,4]triazolo[1,5-a]pyridinides and their neutralization to 2-aryl[1,2,4]triazolo[1,5-a]pyridines

A one step synthesis of novel piperidinium 2-aryl[1,2,4]triazolo[1,5-a]pyridinides 6 from 2′-benzoyl-2-cyanoacetohydrazide (2) and α-substituted cinnamonitriles 3 is described. The reaction takes place by 6-exodig cyclization followed by an 5-exo-trig process to afford salts 6 . The X-ray diffraction of compound 6a reveal that the cation is strongly linked to the anion by hydrogen bonds and a characteristic partial stacking motive. 2-Aryl[1,2,4]triazolo[1,5-a]pyridines were obtained from salts 6 by treatment with hydrochloric acid.     

Reductive photocyclization of benzo[b]furans and their analogs

The UV irradiation of substituted 2,3-diphenylbenzo[b]furans and of 2,3-diphenyl-5-t-butylfuran in n-propylamine gives 1,4-dihydro derivatives of the corresponding aromatic cyclized compounds. This reaction does not involve a photoreduction. It can be concluded from deuterium labelling experiments that H atoms of the alkyl chain of n-propylamine are incorporated in the product. When the solvent is not an unhindered primary amine, only totally aromatic photocyclized products are obtained. It is proposed that hydrogens eliminated during formation of the isolated compounds are released in a reductive form and not as radicals. This is supported by the fact that acenaphthylene is reduced when irradiated in n-propylamine together with 2,3-diphenylbenzo[b]furan under conditions which do not promote, photoreduction. This seems to be a general finding in that the irradiation of stilbene in n-propylamine to acenaphthylene is the same as that of 2,3-diphenylbenzo[b]furan.     

Preparation of 2,3-Dihydro [1,5] Benzothiazepines and 2,3-Dihydro [1,5] Benzodiazepines

2,3-dihydro[1,5] benzothiazepines and diazepines can be prepared by condensation of o-aminothiophenol or o-phenylenediamines with a variety of 3-chlorothieno-or benzothienopropanones.     

1-methoxy-3,5-diaryl-2-oxabicyclo[4.4.0]dec-3-enes from “semicyclic” 1,5-diketones

It was established that semicyclic 1,5-diketones are capable of reacting with methanol by the catalytic action of hydrogen chloride and are capable of forming 1-methoxy-3,5-diaryl-2-oxabicyclo [4.4.0]dec-3-enes — cyclic acetals that include an alkoxydihydropyran ring. In addition, 2,4-darylbicycle[3.3.1]non-2-en-9-ones, which are formed from 1,3-diaryl-3-(2-oxocyclohexyl)propan-1-ones by an intramolecular condensation of the erotonic type, are detected as side products. The possible mechanism of the reaction of 1,3-diaryl-3-(2-oxocyclohexyl)propan-1-ones with methanol in the presence of hydrogen chloride is discussed.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 470–473, April, 1979.     

Thiopyrans and thiopyrylium salts from 1,5-diketones

It has been established that with hydrogen sulfide and hydrogen chloride acyclic 1,5-diketones form thiopyrans, thiopyrylium chlorides, or mixtures of them, depending on their structure and the reaction conditions. Some reactions of thiopyrylium chlorides and thiopyrans obtained for the first time have been studied.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 7, pp. 900–907, July, 1970.     

7-Aryl-6,7-dihydro-8h-indeno[1′,2′∶2,3]pyrano-[5,6-c]benzo[c]pyran-6,8-diones and their thio analogs

The ability of 3-[-(1,3-dioxo-2-indanyl)benzyl]-4-hydroxy-substituted 2H-benzo [b]pyran-2-ones and benzo[b]thiopyran-2-ones to undergo dehydration under the influence of dehydrating agents to give 7-aryl-6,7-dihydro-8H-indeno[1,2-2,3]pyrano[5,6-c]benzo[c]pyran-6,8-diones and their thio analogs was demonstrated.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1475–1476, November, 1985.     

Quinazolines and 1,4-benzodiazepines. LXXVIII Pyrazolo[1,5-a] [1,4]-benzodiazepines and Imidazo[1,5-a] [1,4]benzodiazepinones

The syntheses of novel 8-chloropyrazolo[1,5-a][1,4]benzodiazepines and of an imidazo-benzodiazepinone utilizing products from the nucleophilic substitution of fluorine in 2-fluoro-5-nitrobenzophenone ( 1 ) by pyrazole-3,5-dicarboxylic acid, dimethyl ester ( 2 ) and by 2-methyl-imidazole-4,5-dicarboxylic acid, diethyl ester ( 30 ) are described.     

Polymethine dyes based on cyclohepta[c]pyrrole

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1432–1433, October, 1991.     

Synthesis of novel 1,2,3,4-tetrahydrobenzo[c]-1,5-naphthyridines from pyrrolo[1,2-b]isoquinolines

1,2,3,4-Tetrahydrobenzo[c]-1,5-naphthyridine ( 5a ) was prepared by a novel synthetic route involving the rearrangement of (±)-(Z)-1,10a-dihydropyrrolo[1,2-b]isoquinoline-3,10(2H,5H)-dione oxime to afford 1,4-dihydrobenzo[c]-1,5-naphthyridin-2(3H)-one, which was reduced to 5a. The cholinomimetic activity observed with 5a prompted the synthesis and biological evaluation of additional analogues.     

New [g]-fused [1,2,4]triazolo[1,5-c]pyrimidines: Synthesis of pyrido[3,2-e] and [4,3-e][1,2,4]triazolo[1,5-c]pyrimidine,pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidine and [1,2,4]triazolo[1,5-c]pteridine derivatives

A number of 2-aryl-substituted pyrido[3,2-e] and [4,3-e][1,2,4]triazolo[1,5-c]pyrimidines and [1,2,4]triazolo[1,5-c]pteridines 11,12a,b,e , their corresponding 5-carbonyl derivatives 7,8a,b,e and some pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ones 7,8c,d have been synthesized, according to different pathways. The new tricyclic heterocycles were prepared with the aim of studying their possible benzodiazepine receptors affinity.