The reaction of aminoamides of the furo[2,3-b]pyridine series with an aqueous solution of sodium hypochlorite and N-chlorosuccinimide was studied. It was found that the chlorination reaction proceeds at position 2 of the furopyridine system, leading to previously unknown 3-imino-2-chlorofuro[2,3-b]pyridine-2-carboxamides. For some synthesized compounds, nucleophilic substitution reactions were investigated. Among the obtained substances, compounds were identified that have antidote activity against 2,4-D.

An entry from the Cambridge Structural Database, the world’s repository for small molecule crystal structures. The entry contains experimental data from a crystal diffraction study. The deposited dataset for this entry is freely available from the CCDC and typically includes 3D coordinates, cell parameters, space group, experimental conditions and quality measures.

( E )-3-Aryl-2-cyanoprop-2-entioamides, prepared by Knoevenagel condensation between aromatic aldehydes and cyanothioacetamide, react with sodium nitrite in acetic acid to form (2 E ,2′ E )-2,2′-(1,2,4-thiadiazole-3,5-diyl)bis[3-arylacrylonitriles]. A possible mechanism and limitations of the reaction are discussed. Molecular docking was carried out in order to search for possible protein targets for the obtained 1,2,4-thiadiazoles. One of the compounds showed a pronounced antidote effect against the herbicide 2,4-D in a laboratory experiment on sunflower seedlings and under field conditions.

A new series of thienopyridine derivatives, namely N-(thieno[2,3-b]pyridin-3-yl)aminoalcohols, was obtained by a cascade deacylation/alkylation reaction of 3-aminothieno[2,3-b]pyridine ketones. An alternative approach to the synthesis of these compounds by alkylation of 3-aminothienopyridines unsubstituted at position 2 with diols was proposed.

The reaction of N-substituted amides of 3-amino-4,6-diarylthieno[2,3-b]pyridine-2-carboxylic acids with ninhydrin in the presence of catalytic amounts of sulfuric acid gave 1′-spiro[indene-2,2′-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine]-1,3,4′(3′H)-triones. Structure of a number of key compounds was studied using 2D NMR spectroscopy; the bioavailability parameters of the obtained compounds in silico were calculated. In a laboratory experiment, a moderate antidote effect was revealed with respect to the 2,4-D herbicide for one compound.

Aminomethylation of xanthane hydride (5-amino-1,2,4-dithiazole-3-thione) with the RNH2–HCHO system has resulted in the formation of the derivatives of new heterocyclic system (3,7-dihydro-5H-[1,2,4]-dithiazolo[4,3-a][1,3,5]triazine) in low yields. The reaction of xanthane hydride with dicyandiamide has led to thioammeline [4,6-diamino-1,3,5-triazine-2(5Н)-thione]. Some practically important properties of xanthane hydride and its derivatives have been investigated. Xanthane hydride has efficiently exhibited carbon steel corrosion in neutral aqueous media. The prepared compounds have not exhibited growth-regulating or antidote activity to herbicide 2,4-D.

ChemInformVolume 46, Issue 24 Preparative Organic Chemistry ChemInform Abstract: Novel Rearrangement of 3-Acylaminofuro[2,3-b]pyridines (I) into 3-(Oxazol-4-yl)pyridin-2-ones (II). Tatyana A. Stroganova, Tatyana A. Stroganova Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorVladimir K. Vasilin, Vladimir K. Vasilin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorPolina S. Shestakova, Polina S. Shestakova Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorViktor M. Red'kin, Viktor M. Red'kin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorGennady D. Krapivin, Gennady D. Krapivin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this author Tatyana A. Stroganova, Tatyana A. Stroganova Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorVladimir K. Vasilin, Vladimir K. Vasilin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorPolina S. Shestakova, Polina S. Shestakova Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorViktor M. Red'kin, Viktor M. Red'kin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorGennady D. Krapivin, Gennady D. Krapivin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this author First published: 27 May 2015 https://doi.org/10.1002/chin.201524036Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume46, Issue24June, 2015 RelatedInformation

The reaction of secondary 3-aminothieno[2,3-b]pyridine-2-carboxamides with ortho-formylbenzoic acid gave angular (±)-7,7a-dihydropyrido[3",2":4',5']thieno[2',3':5,6]pyrimido[2,1-a]isoindole-6,12-diones. The intermediate products, (±)-(1,2,3,4-tetrahydropyrido[3',2':4,5]thieno[3,2-d]pyrimidin-2-yl)benzoic acids, were isolated in some cases. Secondary N-[(5-methylfuran-2-yl)methyl]carboxamides were shown to form linear isoindole-6,8-diones in this reaction. One of the angular isoindole-6,12-dione derivatives was studied by X-ray structural analysis. Dynamic NMR was used to characterize the degenerate intramolecular rotation in molecules of isoindole-6,12-diones.

It has been shown that the reaction of primary 3-aminothieno[2,3-b]pyridine-2-carboxamides with o-formylbenzoic acid gives 12b,13-dihydropyrido[3″,2″:4′,5′]thieno[3′,2′:4,5]pyrimido[2,1- a ]iso-indole-6,8-diones. Heterocorrelation NMR spectroscopy and X-ray structural analysis showed that the molecules of the compounds obtained have a linear, double folded stereo structure.

We describe a two-stage synthesis of heptacyclic structures, isoindolo[1',2':2,3]pyrido[3",2":4',5']-thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6(10bH)-ones, and intermediates, 5,6-dihydropyrido-[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6-yl]benzoic acids, as products from the interaction of 3-amino-2-benzimidazolylthieno[2,3-b]pyridines and ortho-formylbenzoic acids. 5,6-Di-hydropyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6-yl]benzoic acids were shown to easily oxidize (aromatize) to the corresponding pyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]-benzimidazol-6-yl]benzoic acids. The molecular and crystal structures of 4-(methoxymethyl)-2-methyl-isoindolo-[1',2':2,3]pyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6(10bH)-one and 2-[4-(methoxymethyl)-2-methylpyrido[3",2":4',5']thieno[3',2':4,5]pyrimido[1,6-a]benzimidazol-6-yl]- benzoic acid were studied by X-ray crystallography.

ChemInformVolume 45, Issue 21 Preparative Organic Chemistry ChemInform Abstract: Substituted 2-Formylbenzoic Acids (II) in the Synthesis of 11H-Isoindolo[2,1-a]benzimidazol-11-ones (IV), 5H-Isoindolo[2,1-a][3,1]benzoxazine-5,11(6aH)-diones (VI), and 6,6a-Dihydroisoindolo[2,1-a]quinazoline-5,11-diones (VIII). E. V. Gromachevskaya, E. V. Gromachevskaya Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorA. V. Fin'ko, A. V. Fin'ko Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorA. V. Butin, A. V. Butin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorK. S. Pushkareva, K. S. Pushkareva Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorV. D. Strelkov, V. D. Strelkov Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorL. I. Isakova, L. I. Isakova Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorG. D. Krapivin, G. D. Krapivin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this author E. V. Gromachevskaya, E. V. Gromachevskaya Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorA. V. Fin'ko, A. V. Fin'ko Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorA. V. Butin, A. V. Butin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorK. S. Pushkareva, K. S. Pushkareva Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorV. D. Strelkov, V. D. Strelkov Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorL. I. Isakova, L. I. Isakova Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this authorG. D. Krapivin, G. D. Krapivin Kuban State Technol. Univ., Krasnodar 350072, RussiaSearch for more papers by this author First published: 08 May 2014 https://doi.org/10.1002/chin.201421030Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume45, Issue21May 27, 2014 RelatedInformation

Syntheses are reported for a new series of 2-substituted 4,4-diphenyl-3,4-dihydroquinazolines by the reaction of o-aminophenyldiphenylcarbinol (APC) with various nitriles. The reaction of APC with substituted 5-bromo-3-cyano-2(1H)-pyridones leads to the formation of derivatives of two products: 3,4-dihydroquinazolines and 4H-3,1-benzoxazines. The alkylation of 3,4-dihydroquinazolines using dimethyl sulfate proceeds through N,N-dimethylation. The structure of these products is a function of the nature of the substituent at C-2 atom of the heterocycle.

AbstractThermal decomposition of the title azides (II) is accompanied by an intramolecular cyclization furnishing novel fused benzodiazepinone derivatives (III).

A method for the synthesis of 2-methyl-1-[(5-methylfuran-2-yl)methyl]-1H-benzimidazoles based on the intramolecular cyclization of vicinal N-[(5-methylfuran-2-yl)methyl]aminoanilides has been developed. A study was carried out on the protolytic opening of the furan ring leading to the formation of a diketone fragment, which was then used for the formation of N-substituted pyrrole ring by the Paal–Knorr method. The effect of the nature of the amine on the cyclization was demonstrated.

The reaction of vicinal thieno[2,3- b ]pyridine aminoamides with Lawesson’s reagent gave new condensed diazaphosphinine derivatives. The structure of the substituent at the amide nitrogen atom and the reagent ratio were found to affect the direction of this reaction.