- Conversion of formyl into cyano groups in kojic acid derivatives and analogues
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It has been revealed that N,N-dimethylhydrazones (1a-c, 3a,b) derived from kojic acid analogs, such as substituted furans (3a,b), 4-pyrones (1a,b) and 4-pyridine (1c), on oxididation with 3-chloroperoxybenzoic acid afford the corresponding nitriles (2a-c,
- Mlochowski, Jacek,Giurg, Miroslaw,Uher, Michal,Korenova, Anna,Vegh, Daniel
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- Hydroperoxide oxidation of different organic compounds catalyzed by silica-supported selenenamide
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The recoverable heterogeneous silica-supported catalyst selenenamide 2 was prepared by the coupling of 3-aminopropylsilicate (4) with 2-chloroselenobenzoyl chloride (6). Its catalytic activity was demonstrated in tert-butyl hydroperoxide oxidation of aldehydes 8 to carboxylic acids 9 and benzylamines 17 to nitriles 18. Moreover, it was employed for hydrogen peroxide oxidation of azomethine compounds such as tosylhydrazones 10, oximes 13 and N,N-dimethylhydrazones 16 to parent ketones 12, arenecarboxylic acids 11 and 15, their methyl esters 14 and nitriles 18 depending on the substrate used and the reaction conditions. The catalyst was simply recovered by filtration and could be reused.
- Giurg,Brzaszcz,Mlochowski
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p. 417 - 428
(2007/10/03)
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- Efficient transformation of aldoximes to nitriles using 2-chloro-1-methylpyridinium iodide under mild conditions
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Various (aliphatic, aromatic, and heterocyclic aromatic) types of aldoximes were converted into the corresponding nitriles in good to excellent yields using 2-chloro-1-methylpyridinium iodide (CMPI) as a dehydrating agent under mild conditions.
- Lee, Kieseung,Han, Sang-Bae,Yoo, Eun-Mi,Chung, Soon-Ryang,Oh, Haibum,Hong, Sungwan
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p. 1775 - 1782
(2007/10/03)
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- Synthesis and biological activity of nitro heterocycles analogous to megazol, a trypanocidal lead
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As part of our efforts to develop new compounds aimed at the therapy of parasitic infections, we synthesized and assayed analogues of a lead compound megazol, 5-(1-methyl-5-nitro-1H-2-imidazolyl)-1,3,4-thiadiazol-2-amine, CAS no. 19622-55-0), in vitro. We first developed a new route for the synthesis of megazol. Subsequently several structural changes were introduced, including substitutions on the two rings of the basic nucleus, replacement of the thiadiazole by an oxadiazole, replacement of the nitroimidazole part by a nitrofurane or a nitrothiophene, and substitutions on the exocyclic nitrogen atom for evaluation of an improved import by the glucose or the purine transporters. Assays of the series of compounds on the protozoan parasites Trypanosoma brucei, Trypanosoma cruzi, and Leishmania donovani, as either extracellular cells or infected macrophages, indicated that megazol was more active than the derivatives. Megazol was then evaluated on primates infected with Trypanosoma brucei gambiense, including late-stage central nervous system infections in combination with suramin. Full recovery was observed in five monkeys in the study with no relapse of parasitemia within a 2 year follow-up. Because there is a lack of efficacious treatments for sleeping sickness in Africa and Chagas disease in South America, megazol is proposed as a potential alternative. The mutagenicity of this compound is at present being reevaluated, and metabolism is also under investigation prior to possible further developments.
- Chauvière, Gérard,Bouteille, Bernard,Enanga, Bertin,De Albuquerque, Cristina,Croft, Simon L.,Dumas, Michel,Périé, Jacques
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p. 427 - 440
(2007/10/03)
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- Hydrogen peroxide oxidation of N,N-dimethylhydrazones promoted by selenium compounds, titanosilicalites or acetonitrile
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Hydrogen peroxide oxidation of N,N-dimethylhydrazones 1 promoted by title reagents has been investigated. Depending on the substrate nitrile 2 and/or amide 3 accompanied with carboxylic acid 4 and parent carbonyl compounds 5 were obtained. Formation of nitriles 2 with H2O2-acetonitrile system is limited for a few more active substrates. The mechanism of the reaction, based on generated in situ peroxyiminoacetic acid, is presented. A broad spectrum of aliphatic, unsaturated and aromatic nitriles 2 was obtained by oxidation of corresponding N,N-dimethylhydrazones 1 with hydrogen peroxide in the presence of poly(bis-9,10-anthracenyl) diselenide (PADS) (7) as catalyst.
- Giurg,Mlochowski,Ambrozak
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p. 1713 - 1720
(2007/10/03)
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- A simple method for the synthesis of 5-substituted 2-cyanofurans
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A new method based on the Schmidt reaction was developed for the production of 5-R-2-cyanofurans from 5-R-furfurals.
- Pavlov
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p. 524 - 529
(2007/10/03)
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- Elimination reactions of (Z)-thiophene- and (Z)-furan-2-carbaldehyde O- benzoyloximes. Effect of β-aryl group upon the nitrile-forming anti transition state
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Elimination reactions of (Z)-thiophene- and (Z)-furan-2-carbaldehyde O- benzoyloximes 1 and 2 with DBU in MeCN have been investigated kinetically. The reactions are second order and exhibit substantial values of Hammett ρ and k(H)/k(D) values, and an E2 m
- Cho, Bong Rae,Cho, Nam Soon,Song, Sang Hun,Lee, Sang Kook
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p. 8304 - 8309
(2007/10/03)
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- SYNTHESIS AND PROPERTIES OF 5-FURYL(ARYL)-Δ2-1,2,4-TRIAZOLINES AND -Δ2-1,3,4-THIADIAZOLINES. MOLECULAR AND CRYSTAL STRUCTURE OF 2-ACETYLAMINO-5-PHENYL-Δ2-1,3,4-THIADIAZOLINE
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We show that upon acylation of arylidene amidrazones of 5-nitro-2-furancarboxylic acid, 3-(5-nitro-2-furyl)-Δ2-1,2,4-triazolines or 5-(5-nitro-2-furyl)-1,2,4-triazole are formed (depending on the structure of the arylidene moiety). Δ2/sup
- Usova, E. B.,Krapivin, G. D.,Zavodnik, V. E.,Kul'nevich, V. G.
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p. 1158 - 1164
(2007/10/03)
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- SYNTHESIS OF 5-SUBSTITUTED CYANOFURANS AND THEIR REACTION WITH HYDRAZINE
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Based on the Schmidt reaction, a new method has been developed for the preparation of nitriles in furan series from the corresponding furfural derivatives.Depending on conditions, the reaction of 5-substituted cyanofurans with hydrazine leads to amidrazones, N-aminotriazoles, or 1,2,4,5-dihydrotetrazines.
- Pavlov, P. A.,Kul'nevich, V. G.
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p. 140 - 145
(2007/10/02)
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- A Useful Method for the Conversion of Aldehyde Oximes into Nitriles Using 1,1'-Oxalyldiimidazole
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Under neutral conditions, aliphatic, alicyclic, aromatic, and heteroaromatic aldehyde oximes (3) react with 1,1'-oxalyldiimidazole (2) in an appropriate solvent such as benzene, acetonitrile, chloroform, or tetrahydrofuran at 65-70 degC within 1 h to give the corresponding nitriles (4) in good yield.Keywords --- dehydration; 1,1'-carbonyldiimidazole; 1,1'-oxalyldiimidazole; oxime; nitrile
- Kitagawa, Tokujiro,Sasaki, Hideaki,Ono, Noriyuki
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p. 4014 - 4016
(2007/10/02)
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- SYNTHESIS AND REACTIONS OF TRIMETHYLAMMONIUM SALTS OF 5-NITRO-2-FURAN AND 5-NITRO-2-THIOPHENE. THE PREPARATION OF 5-NITRO-2-FURYL- AND 5-NITRO-2-THIENYL AZIDE
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Preparation of new water-soluble derivatives of 5-nitro-2-furan and 5-nitro-2-thiophene from 2-bromo-5-nitrofuran (Ia) or 2-bromo-5-nitrothiophene (Ib) and trimethylamine is described.The trimethylammonium derivatives IIa, IIb react with the azide or cyan
- Vegh, Daniel,Kovac, Jaroslav,Dandarova, Miloslava
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p. 1885 - 1890
(2007/10/02)
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