Functional derivatives of thiophene

A method is proposed for the synthesis of 5-acylamino-2,3-dimethylthiophene-4-carbaldehydes and 5-acylamino-2,3-tetramethylenethiophene-4-carbaldehydes by the formylation of the corresponding thiophenes using the Vilsmeier reaction. From the formyl derivatives obtained, previously unaccessible derivatives of thieno[2,3-b]pyridine, thieno[2,3-d]pyrimidine, and thieno[3′,2′∶5,6]pyrido[2,3-d]-pyrimidine have been synthesized.     

Pyrylium derivatives of steroid hydroxymethyleneketones

Chemistry of Natural Compounds - A number of derivatives of androstano [3, 2-b] pyrylium and androst-13-eno-[3, 2-b] pyrylium derivatives forming a new class of heterocyclic steroids has been...     

Mononitration of derivatives of benzisatins

The mononitration of benz[e]-, benz[f]-, and benz[g]isatins and their tetrahydro derivatives was realized. It was established on the basis of an analysis of the ¹H NMR and mass spectra that substitution takes place at position 5 in the derivatives of the [g] series and at the position adjacent to the NH group in derivatives of the [f] series and in the case of 6,7,8,9-tetrahydrobenz [e]isatin. This reaction path corresponds to the maximum electron density in the HOMO, calculated by the CNDO method. In benz[e]isatin, contrary to the general relationship and to the quantum-chemical prediction, the nitro group initially enters the ring annellated with the indole ring.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 60–65, January, 1989.     

Synthesis of deuterium-labeled derivatives of dimethylallyl diphosphate

Short practical syntheses for five deuterium-labeled derivatives of dimethylallyl diphosphate (DMAPP) useful for enzymological studies are reported. These include the preparation of the C1-labeled derivatives (R)-[1-2H]3-methylbut-2-enyl diphosphate ((R)-[1-2H]1-OPP) and (S)-[1-2H]3-methylbut-2-enyl diphosphate ((S)-[1-2H]1-OPP), the C2-labeled derivative [2-2H]3-methylbut-2-enyl diphosphate ([2-2H]1-OPP), and the methyl-labeled derivatives (E)-[4,4,4-2H3]3-methylbut-2-enyl diphosphate ((E)-[4,4,4-2H3]1-OPP) and (Z)-[4,4,4-2H3]3-methyl-but-2-enyl diphosphate ((Z)-[4,4,4-2H3]1-OPP).     

Functional derivatives of thiophene

2-Aryl-4-oxothieno[2,3-d]oxazine derivatives were synthesized. Opening of the oxazine ring to give 2-benzamidothiophene-3-carboxylic acid hydrazide derivatives is observed when these compounds are treated with hydrazine hydrate.See [1] for Communication 17.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 45–46, January, 1980.     

Electron-rich and electron-poor pentalene derivatives

Bisdialkylaminoalkylidene derivatives of dihydroindeno[2,1-a]indene as electron-donors, and dihydroindeno-[2,1-a]indene-5,10-dione-biscyanoimines and bisdicyanomethylene-dihydroindeno[1,2-b]fluorenes as acceptors have been prepared and found to form charge transfer complexes with interesting electrical conductivities.     

Synthesis of thiopheno-quinizarine derivatives

4,11-Dihydroxyanthra[2,3-b]thiophene-5,10-dione (thiophenoquinizarine) and its 3-methyl derivative were obtained by the cyclization of quinizarin-2-yl derivatives of mercaptoacetaldehyde or mercaptoacetone in acid medium. 4,11-Dimethoxy-and 4,11-dibutoxyanthra[2,3-b]thiophene-5,10-dione were synthesized by the alkylation of the hydroxyl group in the synthesized anthrathiophenes with dimethylformamide dimethylacetal or butyl iodide respectively. Radical bromination of 4,11-dimethoxy-3-methylanthra[2,3-b]thiophene-5,10-dione, depending on the amount of N-bromo-succinimide taken, leads to the formation of 3-bromomethyl-or 3-dibromomethyl-4,11-dimethoxy-anthra[2,3-b]thiophene-5,10-diones. The action of sodium acetate on the obtained bromo derivatives with subsequent hydrolysis of the intermediate acetates led to the synthesis of 3-hydroxymethyl-or 3-formyl-4,11-dimethoxy-anthra[2,3-b]thiophene-5,10-diones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1478–1485, October, 2007.     

Pyrazoline derivatives: A convenient synthetic route to new pyrazolo-benzothia-(oxa) or diazepinone derivatives

New pyrazolo-[3,4-b]-[1,5]-benzoazepinone derivatives are reported. One pot reactions of 5-chloro-4-carboxy-1-phenyl (3-substituted) pyrazole derivatives with o-thioaminophenol, o-phenylenediamine, and o-aminophenol derivatives were realized. The influences of the polarizability of the heteroatoms on the reaction rates and chemical yields are discussed. © John Wiley & Sons, Inc.     

A novel one-pot synthesis of some new interesting pyrrole derivatives

[reaction: see text] 11-(1H-Pyrrol-1-yl)-11H-indeno[1,2-b]quinoxaline and 3-(1H-pyrrol-1-yl)indolin-2-one derivatives have been synthesized in good yields in a novel, one-pot, and efficient process by condensation of 11H-indeno[1,2-b]quinoxalin-11-one or isatin derivatives with 4-hydroxyproline on solid-support montmorillonite K10 under microwave irradiation.     

Heterocyclization of functionalized vinylic derivatives of imidazo

Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-a]pyridines was explored experimentally and theoretically using semiempirical AM1 and ab initio methods. A range of functionalized vinylic derivatives (azido, amino, and carbodiimide groups) were prepared for conversion into pyrroloazaindoles 19-22, imidazo[1,x]-, (x = 5, 6, 7, 8), [2,6]-, and [2,7]naphthyridines 28-30, 35-38 by thermal reaction. In the case of vinylic groups in the 5 position, peri annulation also was observed. The experimental and theoretical data are compared and discussed.     

Reactions of some new thienothiophene derivatives

Facile and convenient syntheses of bisdimethylthieno[2,3-b]thiophen-2,5-diyl bis(oxazole-2-amine), bis(1H-imidazol-2-amine), bis((3a)-H-indole),[1,2-a]pyrimidine), bis(1H-imidazo[1,2-b][1,2,4]triazole) and bis(9H-benzo[d]imidazo[1,2-a]imidazole) derivatives incorporating a thieno[2,3-b]thiophene moiety from the versatile and readily accessible 1,1'(3,4-dimethylthieno[2,3-b]thiophene-2,5-diyl)-bis(2-bromo-ethanone) (1) are described.     

Functional derivatives of thiophene

The derivatives obtained by reaction of o-halonitrothiophenes with cyanoacetic and acetoacetic esters were converted to thieno[2,3-b]- and thieno[3,2-b]pyrroles by reductive cyclization.See [1] for communication VI.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1628–1630, December, 1973.     

Effect of the glutaraldehyde derivatives of Calix[n]arene as cross-linker reagents on lipase immobilization

Synthesis of the glutaraldehyde derivatives calix[n]arene (n = 4,6,8) (Calix[n]-GA) and using as cross-linkers for immobilization of Candida rugosa lipase (CRL) have been discussed in this paper. The amino functional calix[n]arene derivatives (Calix[n]-NH ₂) were synthesized via reduction of dinitrile, hexanitrile and octanitrile derivatives of calix[n]arenes. These amino functional calix[n]arene derivatives (Calix[n]-NH ₂) were converted to their aldehyde derivativatives with glutaraldehyde. The calix[n]arene derivatives were used in lipase immobilization in order to see the role of calix[n]arene binding site on the lipase activitiy and stability. The activity recovery of calix[n]arene-supported lipases (Calix[n]-CRL) based on the Calix[4]-CRL, Calix[6]-CRL and Calix[8]-CRL reaches to 53.5, 66.1 and 76.4%, respectively.     

Functional derivatives of thiophenes

2,3-Polymethylene-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine derivatives were obtained by reaction of esters of α-aminothiophene-β-carboxylic acids with lactame or α-aminothiophene-Β-carboxylic acids with lactims. Desulfuration of the thienopyrimidines obtained in this manner is a convenient method for the synthesis of pyrrolo-, pyrido-, and azepino[1,2-a]pyrimidine derivatives.     

Rearrangements of haloalkynol derivatives of glucofuranose

Bromoalkynol derivatives of diacetone glucose undergo rearrangements to dihaloenol ethers contained in furo[3,4-b]furan cores when treated with halonium-producing reagents. [reaction: see text]     

Functional thiophene derivatives

The thiocyanation of 5-acylaminothiophenes gives 4-thiocyanato derivatives, the intramolecular cyclization of which gives 2-acylaminothieno[2,3-d]thiazoles.See [1] for communication VIII.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1204–1205, September, 1974.     

Synthesis of benzo[g]quinoline derivatives

The electronic spectra of linear benzo[g]quinoline, its 4-substituted derivatives, and some hydrogenated derivatives are examined and discussed.See [1] for communication IX.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 662–665, May, 1972.     

Condensed thienopyrimidines. II. Synthesis and gastric antisecretory activity of thiazole and polymethylene condensed thienopyrimidine derivatives

Thiazolo[3,2-a]thieno[3,2-d]-, [3,4-d]- and [2,3-d]pyrimidin-5-one derivatives (6, 11 and 16), and polymethylene condensed thieno[3,2-d]-, [3,4-d]- and [2,3-d]pyrimidin-5-one derivatives (19-21), in which the oxygen atom of the oxazolidine moiety in 3 was replaced by a sulfur atom or methylene groups, were synthesized and evaluated for gastric antisecretory activity in pylorus-ligated rats. The structure-activity relationships of these compounds are discussed.     

Protection-deprotection method in synthesis of calixarene derivatives

The debenzylation and selective de-tert-butylation of p-tert-calix[4]arene derivatives were studied and 11,17,23-tri-tert-butyl-25,26,27-tri-O-etherated calix[4] arenes were synthesized by a simultaneous debenzylation and selective de-tert-butylation process.     

Photochromism of triangle terthiophene derivatives as molecular re-router

2,2[prime or minute]-3,3[double prime]-Terthiophene derivatives undergo photochemically reversible cyclization and cycloreversion reactions. The absorption peak wavelength changed systematically with substitution of the phenyl rings at 5-, 5[prime or minute]- and 5[double prime]-positions of the thiophene rings, which indicates re-routing of the [small pi]-conjugation system.