Synthesis and structure of 2-ethoxy- and 2-aminomethylidene-3-fluoroalkyl-3-oxopropionates

Condensation of ethyl 3-polyfluoroalkyl-3-oxopropionates with excess triethyl orthoformate gave ethyl 3-polyfluoroalkyl-2-ethoxymethylidene-3-oxopropionates which reacted with primary aliphatic, aromatic, and heterocyclic amines to form ethyl 2-alkyl(aryl, hetaryl)aminomethylidene-3-polyfluoroalkyl-3-oxopropionates. According to the X-ray diffraction and IR data, the latter exist in the crystalline state as the corresponding E isomers, while in solution (NMR data), as mixtures of Z and E isomers. Condensation of ethyl 2-ethoxymethylidene-3-oxopropionates with secondary heterocyclic amines (morpholine and pyrrolidine) led to the formation of 2-morpholino(pyrrolidin-1-yl)methylidene-3-fluoroalkyl-3-oxopropionates which were shown to exist as Z isomers both in the crystalline state and in solution.     

Alkyl 3-fluoroalkyl-3-oxopropionates in reactions with azolyldiazonium salts

Alkyl 3-fluoroalkyl-3-oxopropionates react with antipyrinyldiazonium chloride to form 2-antipyrinylhydrazono-3-fluoroalkyl-3-oxopropionates. The use in these reactions of hetaryldiazonium salts, containing NH group in the α position, leads to alkyl 7-fluoroalkyl-7-hydroxy-4,7- dihydroazolo[5,1-c]triazine-6-carboxylates. 3-Amino-1H-1,2,4-triazole, 3-amino-4-ethoxycar- bonyl-1H-pyrazole, and 5-amino-4-ethoxycarbonyl-1H-imidazole were used as the heterocyclic component. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 599–603, March, 2008.     

Synthesis of 3-aryl(hetaryl)-1,2,3-diazaphospholines

A reaction of cyclohexanone phenylhydrazone with (het)aryldihalogenophosphines has been studied. As shown, cyclohexanone phenylhydrazone reacts with phenyldibromophosphine and 5-methyl-2-furyldibromophosphine to provide the corresponding 1,2,3-diazaphospholines in high yields. The diazaphospholines thus obtained have been derivatized. © 2005 Wiley Periodicals, Inc. Heteroatom Chem 16:81–83, 2005; Published online in Wiley InterScience (www.interscience.wiley.com). DOI 10.1002/hc.20074     

Synthesis and structure of amides of 4-aryl(hetaryl)-2-pyrrolidone-3-carboxylic acids

Amides of 4-aryl(hetaryl)-2-pyrrolidone-3-carboxylic acids have been prepared via ammonolysis of the corresponding esters of pyrrolidone carboxylic acids. The products structure has been characterized by means of IR, ¹H NMR, ¹H–¹³C HMQC, and HMBC spectroscopy.     

Synthesis of N-arylsulfonyl-2-aryl(hetaryl)aminoacetic acids

Hydrolytic transformations of 4-[2,2,2-trichloro-1-(arylsulfonylamino)-and-(ethoxycarbonylamino)ethyl]phenyloxy(or sulfanyl)acetic acids under microwave irradiation in alkaline medium involve both trichloromethyl group and ester fragment to give N-arylsulfonyl-2-[4-carboxymethyloxy(or sulfanyl)phenyl]-2-aminoacetic acids in good yields. Hydrolysis of methyl 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl)acetates without microwave activation occurs only at the ester group with quantitative formation of 4-[2,2,2-trichloro-1-(arylsulfonylamino)ethyl]phenyloxy(or sulfanyl) acetic acids. N-[2,2,2-Trichloro-1-(1-naphthyl, 2-furyl, and 1-methylindol-3-yl)ethyl]-4-chlorobenzenesulfonamides in alkaline medium under microwave irradiation were converted in 10–15 min into the corresponding N-(4-chlorophenylsulfonyl)-2-aryl-2-aminoacetic acids in preparative yields.     

Hydrazides of 4-aryl(hetaryl)-2-oxopyrrolidine-3-carboxylic acids: Synthesis and structure

Proceeding from reactions of methyl 4-aryl(hetaryl)-2-oxopyrrolidine-3-caroxylates with hydrazine and phenylhydrazine a series of hydrazides of the corresponding 2-oxopyrrolidine-3-carboxylic acids was obtained combining in the molecule a lactam ring and carbohydrazide groups. Phenylhydrazides of 2-oxopyrrolidine-3-carboxylic acids possess the Z-configuration.     

Synthesis of 3-alkylmercapto-2-aryl(alkyl) pyrimidazoles

Summary Conditions were found for replacing the halogen in 3-bromo-2-alkyl(aryl)pyrimidazoles by the alkylmercapto group.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 1671–1673, September, 1965     

Reactions of 2-aryl (hetaryl) methylene-3-oxoquinuclidines with bifunctional nucleophilic reagents

The reactions of 2-aryl(hetaryl)methylene-3-oxoquinuclidines with hydrazine hydrate, thiourea, and phenylhydrazine gave, respectively, 7-phenyl-7,7a,dihydropyrazolo[3,4-b]quinuclidine, 7-(4-methoxyphenyl)-7,7a-dihydropyrazolo[3,4-b]quinuclidine, 7-(2-thienyl)-7,7a-dihydropyrazolo-[3,4-b]quinuclidine, 3,3-azinobis (2-benzylidenequinuclidine), 3,3-azinobis[2-(4-methoxybenzylidene)quinuclidine], 6-thio-8-phenyl-5,6,7,8-tetrahydropyrimido[5,4-b]quinuclidine, 2-benzylidene -3-oxoquinuclidine phenylhydrazone, and 2-(4-methoxybenzylidene)-3-oxoquinuclidine phenylhydrazone. The structures of the compounds were confirmed by the IR and ¹H and ¹³C NMR spectra.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 793–797, June, 1982.     

Synthesis and Structure of (2E)-3-Aryl(hetaryl)-2-[5-bromo-4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles

Russian Journal of General Chemistry - Bromination of (2E)-3-aryl(hetaryl)-2-[4-aryl(hetaryl)-1,3-thiazol-2-yl]acrylonitriles proceeds regioselectively at the C5 atom of the thiazole ring with the...     

4-Het(aryl)-2-pyrrolidone-3(5)-carboxylic acid alkyl(hetaryl)idenecarbohydrazides: synthesis and structure

Russian Chemical Bulletin - 4-Het(aryl)-2-pyrrolidone-3(5)-carboxylic acid hydrazides react with aromatic aldehydes, acetone, and acetophenone to give new representatives of...     

New derivatives of 3-aminoindole. Synthesis of 2-aryl(hetaryl)-3-(3,5-dimethyl-1-pyrazolyl)indoles

The interaction of arylhydrazines with ù-(3,5-dimethyl-1-pyrazolyl)acetophenones and acetyl(2-thiophene) leads to arylhydrazones, which are converted by Fischer cyclization into 2-aryl(thienyl)-3-(3,3-dimethyl-1-pyrazolyl)indoles with substituents in positions 1, 5, and 7.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1662–1669, November, 2004.     

Synthesis and structure of cobalt(II) 1-aryl-3-aryl(alkyl)-5-(benzothiazol-2-yl)formazanates

New mono- and binuclear cobalt(II) complexes based on 1-aryl-3-aryl(alkyl)-5-(benzothiazol-2-yl)formazans were synthesized. The structure of the synthesized compounds was determined by electronic and IR absorption spectroscopy, mass spectrometry, and X-ray crystallography.     

A new synthesis of 6-(alkyl)amino-3-aryl(alkyl)-1,2,4,5-tetrazines

A new method for the preparation of 6-(alkyl)amino-3-aryl(alkyl)-1,2,4,5-tetrazines is described. Dissolving 3-aryl(alkyl)-1,2,4,5-tetrazines in liquid ammonia or a primary aliphatic amine at ?35° to ?40°, followed by addition of potassium permanganate gives the title compounds in reasonable to excellent yields.     

Synthesis of some 5-aryl(hetaryl)tetrazoles by ultrasonication

The influence of ultrasound on the 1,3-dipolar cycloadditio of azides to organic nitriles to form of 1H-5-aryl(hetary)tetrazoles was studied. It was shown that ultrasound decreases the reaction time, and increases the yield of the desired compounds.Institute of Organic Synthesis, Ural Region Russian Academy of Sciences, Ekaterinburg, 620219. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1375–1377. Original article submitted November 1, 1994.     

Dehydrogenation of 4-aryl(hetaryl) spinacine derivatives with dimethyl sulfoxide

Aromatization of 4-aryl(hetaryl)tetrahydroimidazo[4,5-c]pyridine-6-carboxylic acids and their lithium salts by the action of dimethyl sulfoxide has been revealed for the first time. Heating of these compounds in DMSO for 5–7 h at 90–95°C leads to the formation of 4-aryl(hetaryl)imidazo[4,5-c]pyridine derivatives as a result of dehydrogenation and decarboxylation. Heating of the corresponding lithium salts generated in situ (DMSO, 90–95°C, 3–5 h) affords difficultly accessible 4-aryl(hetaryl)imidazo[4,5-c]pyridine-6-carboxylic acids.     

1,2,5-Trimethyl-4-allyl(propargyl)-4-aryl(hetaryl)aminopiperidines

Individual geometrical isomers of some 1,2,5-trimethyl-4-allyl-4-aryl(hetaryl)aminopiperidines were isolated, and their structures were established. 1,2,5-Trimethyl-4-propargyl-4-aryl(aralkyl)aminopiperidines were obtained from 1,2,5-trimethyl-4-aryliminopiperidines and propargylmagnesium bromide.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 942–946, July, 1991.     

Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)ethenes

Reactions of 1-amino-2-nitroguanidine with 2-aryl(hetaryl)-1-nitro-1-ethoxycarbonyl(benzoyl)-ethenes proceed via initial formation the aza-Michael product, are accompanied by liberation of nitroacetic ester (or nitroacetophenone), and result in N-aryl(hetaryl)methylidene-N-(2-nitroguanidino)amines.     

Efficient synthesis of 3-aryl(hetaryl)-1,5,3-dioxazepanes involving catalysts containing Sm and Co

Efficient synthetic procedure was developed for 3-aryl(hetaryl)-1,5,3-dioxazepanes consisting in the transamination of 3-tert-butyl-1,5,3-dioxazepane with arylamines and also by the reaction of 1,2-ethanediol with N,N-bis(methoxymethyl)aryl(hetaryl)amines in the presence of catalytic amounts of Sm and Co compounds.     

Plant coumarins: VIII. Suzuki reaction in the synthesis of 3-aryl(hetaryl)furocoumarins

Suzuki cross coupling of oreoselone trifluoromethanesulfonate with substituted phenyl- and hetarylboronic acids in the presence of palladium complexes with uni- and bidentate ligands gave the corresponding 3-substituted furocoumarins.