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1.
Vladimir Mironov Gulnara Ivkova Liliya Abdrakhmanova Liliya Burnaeva Kristina Kuzmina 《Phosphorus, sulfur, and silicon and the related elements》2013,188(1-3):162-163
Abstract 2-(5-Methyl-2-phenyl-2Н-1,2,3-diazaphosphol-4-yl)-4H-benzo[d]-1,3,2-dioxaphosphorin-4-one 1 readily reacts with hexafluoroacetone, mesoxalic acid diethyl ester, trifluoropyruvic acid ethyl ester and chloral to give 2-(5-methyl-2-phenyl-2H-1,2,3-dizaphosphole-4-yl)-derivatives of 1,3,2- and 1,4,2-dioxaphosphepines. 相似文献
2.
Glukhareva T. V. Morzherin Yu. Yu. Savel"eva E. A. Rozin Yu. A. Tkachev A. V. Bakulev V. A. 《Russian Chemical Bulletin》2001,50(2):268-271
The method for the synthesis of 5-(2,6-dimethylmorpholino)-1,2,3-thiadiazole-4-carbaldehyde was proposed. Its reaction with sodium 1-amino-4-(N-methyl)carbamoyl-1,2,3-triazol-5-olate proceeds through a tandem of the Cornforth rearrangements. The initially formed azomethine isomerizes into sodium 4"-(2,6-dimethylmorpholino)thiocarbonyl-4-(N-methyl)carbamoyl-1,1"-bis[1,2,3]triazolyl-5-olate, which then rearranges to give sodium 4-{N-[4-(2,6-dimethylmorpholinothiocarbonyl)-1,2,3-triazol-1-yl]carbamoyl}-1-methyl-1,2,3-triazol-5-olate. 相似文献
3.
Makoto Kiso Hideki Katagiri Hiroyasu Furui Keiko Ando Hideharu Ishida Akira Hasegawa 《Journal of carbohydrate chemistry》2013,32(2):163-174
Abstract O-(6-O-Benzoyl-β-d-galactopyranosyl)-(1→4)- and O-(2, 3, 4-tri-O-acetyl-β-d-galactopyranosyl)-(1→4)-2, 3, 6-tri-O-benzyl-N-benzyloxycarbonyl-1, 5-dideoxy-1, 5-imino-d-glucitols (4 and 12) were each coupled with methyl (methyl 5-acetamido-4, 7, 8, 9-tetra-O-acetyl-3, 5-dideoxy-2-thio-d-glycero-d-galacto-2-nonulopyranosid)onate (5) in acetonitrile medium in the presence of dimethyl(methylthio)sulfonium triflate (DMTST) or N-iodosuccinimide/trifluoromethanesulfonic acid to give the corresponding α-sialyl-(2 → 3)- and α-sialyl-(2 → 6)-glycosides (6 and 13α), which were converted to novel ganglioside GM3-related trisaccharides (9 and 15) containing N-methyl-1-deoxynojirimycin. 相似文献
4.
Vladimir F. Mironov Gulnara A. Ivkova Liliya M. Abdrakhmanova Rashid Z. Musin Ekaterina V. Mironova Dmitry B. Krivolapov 《Phosphorus, sulfur, and silicon and the related elements》2018,193(1):53-62
The interaction of 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphinin-4-one with mesoxalic and trifluoropyruvic acids ethyl and diethyl esters, hexafluoroacetone and chloral proceeds with an exclusive participation of P(III) atom and allows to obtain 2-(5-methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-derivatives of 1,4,2- and 1,3,2-dioxaphosphepines as well as dichlorovinylphosphonate, being the product of Perkow reaction in the case of chloral. 相似文献
5.
P. Sambasiva Rao K. Chinna Ashalu G. Jitender Dev N. Ravi Kumar P. V. S. S. Srinivas B. V. Thomas 《合成通讯》2017,47(5):457-462
1-Phenyl-1,2,3-triazole-4-carbaldehyde 1 was treated with different N-alkyl hydroxylamine hydrochlorides 2 using NaHCO3 to obtain 1,2,3-triazole substituted N-alkyl nitrones 3a–c. The nitrones 3a–c were further reacted with different substituted olefins and furnished 2-alkyl-3-(1-phenyl-1H-1,2,3-triazol-4-yl)-5-(substituted)isoxazolidine derivatives 4a–p in high yields via 1,3-dipolar cycloaddition reaction. 相似文献
6.
Marcelle de L. Ferreira Marcus V. N. de Souza Solange M. S. V. Wardell James L. Wardell Thatyana R. A. Vasconcelos Vitor F. Ferreira 《Journal of carbohydrate chemistry》2013,32(6):265-274
Five new bis-1,2,3-triazole derivatives from D-mannitol, namely 2,3,4,5-tetra-O-acetyl-1,6-dideoxy-1,6-bis-(4-substituted-1H-1,2,3-triazol-1-yl)-D-mannitol (4), have been synthesized from 2,3,4,5-tetra-O-acetyl-1,6-diazido-1,6-dideoxy-D-mannitol (3) and alkynes, employing copper (I)-catalyzed azide-alkyne cycloaddition (CuAAC) methodology. Evaluation of their in vitro antitubercular activity against Mycobacterium tuberculosis H37Rv using the Alamar Blue susceptibility test indicated poor activities. However, this study has provided information about the SAR of D-mannitol derivatives in the search for new anti-TB drugs based on this carbohydrate. 相似文献
7.
A new and convenient procedure for the synthesis of 1,6-naphthyridin-2(1H)-ones and their derivatives is described. In the first scheme 5-acetyl-6-[2-(dimethylamino)ethenyl]-1,2-dihydro-2-oxo-3-pyridinecarbonitrile ( 4 ) obtained by the reaction of N,N-dimethylformamide dimethyl acetal with 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile ( 3 ) was cyclized to 1,2-dihydro-5-methyl-2-oxo-1,6-naphthyridine-3-carbonitrile ( 5 ) by the action of ammonium acetate. Thermal decarboxylation of acid 7 obtained from the hydrolysis of nitrile 5 led to a mixture of 5-methyl-1,6-naphthyridin-2(1H)-one ( 8 ) and its dimer 9 . Hydrazide 11 obtained from nitrile 5 in two steps was converted to 3-amino-5-methyl-1,6-naphthyridin-2(1H)-one ( 12 ) by the Curtius rearrangement. The amino group of 12 was readily replaced by treatment with aqueous sodium hydroxide to yield 3-hydroxy-5-methyl-1,6-naphthyridin-2(1H)-one ( 13 ). In the second scheme, Michael reaction of enamines of type 20 with methyl propiolate, followed by ring closure gave 5-acyl(aroyl)-6-methyl-2(1H)-pyridinones ( 21 ) which in turn were treated with Bredereck's reagent to produce 5-acyl(aroyl)-6-[2-(dimethylamino)ethenyl]-2(1H)-pyridinones ( 22 ). Treatment of 22 with ammonium acetate led to the formation of 1,6-naphthyridin-2(1H)-ones 23 . 相似文献
8.
《Journal of carbohydrate chemistry》2013,32(3-4):275-283
New oxamides, derivatives of D-glucosamine and aliphatic or aromatic amines were prepared by acylation of methyl 3,4,6-tri-O-acetyl-2-acetamido-2-deoxy-α- or -β-D-glucopyranoside (1c or 1d) with oxalyl chloride, followed by reaction with amine. The reaction was assumed to proceed by the intermediate of N-carbomethoxy N-(methyl 3,4,6-tri-O-acetyl-2-deoxy-α or β-D-glucopyranosid-2-yl) oxamic acid chloride which reacted with amines, and afforded N-acetyl, N-(methyl 3,4,6-tri-O-acetyl-2-deoxy-α- or -β-D-glucopyranosid-2-yl), N′-alkyl or aryloxamide (5–7), and N-(methyl 3,4,6-tri-O-acetyl-2-deoxy-α- or -β-D-glucopyranosid-2-yl), N′-alkyl or aryloxamide (8–13). 相似文献
9.
Some new 1-aryl-4-[(aziridine-1-yl)diaryl-methyl]-5-methyl-1H-1,2,3-triazole derivatives 7j–s were synthesized by the one-pot reaction of diaryl-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)methanol compounds 6j–s formed from 1-aryl-5-methyl-1H-1,2,3-triazole-4-carboxylic acid derivatives. The new compounds 7j–s and 6j–s are investigated by 1H and 13C NMR, MS, and IR. The anticancer activity of the synthesis target compounds was evaluated against human leukemia (HL-60) cells and human hepatoma G2 cells. Some of the compounds were highly efficient. The 1H-NMR signals of the aziridine-ring cis-H/trans-H protons were found to be two group peaks at 1.800–1.884 and 1.183–1.327?ppm. 相似文献
10.
Kaname Tsutsumiuchi Keigo Aoi Masahiko Okada 《Macromolecular rapid communications》1995,16(10):749-755
A novel glycopeptide-containing block copolymer, poly[O-(tetra-O-acetyl-β-D -glucopyranosyl)-L -serine]-block-poly(2-methyl-2-oxazoline) ( 5 ), was synthesized by mutual termination of living polymerizations of a sugar-substituted α-amino acid N-carboxyanhydride (NCA) ( 1 ) and 2-methyl-2-oxazoline ( 3 ). 5 was deacetylated to provide the glycopeptide-polyoxazoline block copolymer, poly[O-(β-D -glucopyranosyl)-L -serine]-block-poly(2-methyl-2-oxazoline) ( 6 ). 相似文献
11.
Cenek Kolar Konrad Dehmel Hans Moldenhauer Manfred Gerken 《Journal of carbohydrate chemistry》2013,32(6):873-890
ABSTRACT Syntheses of 4-O-methyl-β-rhodomycins are described. Glycosylation (trimethylsilyl triflate, dichloromethane-acetone 10:1, -30 °C) of 4-O-methyl-10-O-p-nitrobenzoyl-β-rhodomycinone, obtained from β-rhodomycinone (βRMN) in a 6-step synthesis, with 1-O-tert-butyl(dimethyl)silylated derivatives of 4-O-acetyl- or 4-O-p-nitrobenzoyl-2,3,6-tri-deoxy-3-trifluoroacetylamino-β-L-arabino- and lyxo-hexopyranoses or 2,6-di-O-acetyl-2,6-dideoxy-β-L-lyxo-hexopyranose afforded 7-O-α-L-glycosyl-β-rhodomycinones. Removal of the O- and N-acyl groups with 0.1M and 1M NaOH gave the 7-O-(3-amino-2,3,6-trideoxy-α-L-arabino- and lyxo-hexopyranosyl)-4-O-methyl-β-rhodomycinones and 7-O-(2,6-dideoxy-α-L-lyxo-hexopyranosyl)-4-O-methyl-β-rhodomycinone. 相似文献
12.
Türsen Demir Frederick J. Raveney Robert A. Shaw 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3-4):155-163
Abstract The reactions of 4-methyl-2-[N-(p-toluidinyl)methyl]aniline with phosphorus oxychloride, thiophosphoryl chloride, and their derivatives yield 1,3,2-benzodiazaphosphorine 2-oxides and 2-sulphides. Their 1H NMR and infrared spectra are discussed. Related 1,3,2-benzodiazophosphorine and 1,3,2-dibenzodiazaphosphocine 2-oxides and 2-sulphides are compared. 相似文献
13.
A series of 1,2-azaphospholes, 1,2,3-diazaphospholidine, 1,3,2-diaza-phosphinanes bearing a chromone ring as well as dialkyl pyrazolopyrimidine phosphonates have been synthesized from treatment of multifunctional 2-cyano[(4-oxo-4H-chromen-3-yl)methylidene]acetohydrazide (2), some phosphorus reagents such as phosphonic acid and its esters, and phosphorus sulfides as well as phosphorus halides in dry dioxane. The isolated products were evaluated for their anticancer activities and on the expression of vascular endothelial growth factor (VEGF) inhibition. Among the isolated products, compounds 3 and 10 exhibited higher effect against breast cancer cells than the reference drug and on the expression of VEGF inhibition. 相似文献
14.
2-(5-Methyl-2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-4H-benzo[e]-1,3,2-dioxaphosphorin-4-one reacts with perfluorodiacetyl, 3,6-di(tert-butyl)-1,2-benzoquinone and phenanthrenequinone only with the participation of a three-coordinated phosphorus atom to form spirophosphoranes containing acyclic 5-methyl-2- phenyl-2H-1,2,3-diazaphosphol-4-yl substituent, whereas the interaction with tetrachloro-1,2-benzoquinone proceeds via expanding the six-membered heterocycle to the nine-membered one to form 2-(2-phenyl-2H-1,2,3-diazaphosphol-4-yl)-2,9-dioxo-4,5,6,7-tetrachlorodibenzo[d,h]-1,3,8-trioxaphosphonine. 相似文献
15.
在不同反应条件下反应得到了两种1,2,3-三唑衍生物的配合物[Co(H2O)6][Co(L1)3]2·4H2O(1)和Cu(L2)2(2)(HL1=5-methyl-1-phenyl-1H-1,2,3-triazole-4-carboxylic acid;HL2=1-(4-iodophenyl)-5-methyl-1H-1,2,3-triazole-4-carboxylic acid)。通过X射线单晶衍射和红外光谱确定了晶体结构,同时对配合物1和2进行了表面作用分析(Hirshfeld surface analysis),在二维指纹图谱中可以清楚的看到配合物中的主要分子间作用。 相似文献
16.
Eiji Tanahashi Kyoko Fukunaga Yuko Ozawa Tsuyoshi Toyoda Hidcharu Ishida Makoto Kiso 《Journal of carbohydrate chemistry》2013,32(6):747-768
ABSTRACT A series of sialyl-α-(2→3)-neolactotetraose derivatives containing N-acetyl-(NeuAc), N-glycolyl- (NeuGc) and N-butanoylneuraminic acid, and 3-deoxy-D-glycero-D-galacto-2-nonulosonic acid (KDN) have systematically been synthesized as molecular probes for elucidation of substrate specificity of human α1,3-fucosyltransferases (Fuc-TVII and Fuc-TVI). 2-Methyl-(3,4,6-tri-O-acetyl-1,2-dideoxy-α-D-glucopyrano)-[2',1':4,5]-2-oxazoline (1) was coupled with 2-(trimethylsilyl)ethyl (2,4,6-tri-O-benzyl-β-D-galactopyranosyl)-(1 → 4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (2) to give a trisaccharide 3 which, upon successive O-deacetylation, benzylidenation and reductive opening of the benzylidene group, afforded a common glycosyl acceptor 5. Glycosylation of 5 with sialyl-α-(2→3)-galactose donors 6-8, 19 and 21 gave the corresponding pentasaccharides 22-25, which were converted to a series of sialyl-α-(2→3)-neolactotetraose derivatives 30-33. In the competitive enzyme assay, the NeuGc derivative 32 showed the most potent activity for Fuc-TVII, while the KDN derivative 31 was less active than the standard NeuAc derivative 30. In contrast, the N-butanoylation of neuraminic acid enhanced the activity for Fuc-TVI. 相似文献
17.
N. T. Pokhodylo R. D. Savka V. S. Matiichuk N. D. Obushak 《Russian Journal of General Chemistry》2009,79(2):309-314
By cycloaddition of arylazides to acetylacetone are obtained derivatives of 1,2,3-triazole. In the reaction of 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) and 1-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] ethanones (VIIa-VIIe) with isatin are obtained 2-[1-(R-phenyl)-5-methyl-1H-1,2,3-triazol-4-yl]-4-quinolinecarboxylic acids (IIIa–IIIe) and 2-[4-(4-R-5-methyl-1H-1,2,3-triazol-1-yl)phenyl] -4-quinolinecarboxylic acids (IXa, IXb), respectively. We found that 1-[5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] ethanones (IIa–IIe) readily transform into [5-methyl-1-(R-phenyl)-1H-1,2,3-triazol-4-yl] acetic acids (IVa–IVc) by the method of Wilgerodt-Kindler. The (5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl)acetic acid reacts with 5-phenyl-4-amino-4H-1,2,4-triazol-3-thiol affording 6-[(5-methyl-1-phenyl-1H-1,2,3-triazol-4-yl) methyl]-3-phenyl[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazole (VI).
Original Russian Text ? N.T. Pokhodylo, R.D. Savka, V.S. Matiichuk, N.D. Obushak, 2009, published in Zhurnal Obshchei Khimii,
2009, vol. 79, no. 2, pp. 320–325. 相似文献
18.
N. T. Pohodylo V. S. Matiichuk M. D. Obushak 《Russian Journal of Organic Chemistry》2014,50(2):275-279
Reaction of 5-methyl-1-aryl-1H-1,2,3-triazole-4-carbocylic acid chlorides with tryptamine derivatives afforded substituted 1-aryl-N-[2-(1H-indol-3-yl)ethyl]-5-methyl-1H-1,2,3-triazole-4-carboxamides. At heating these compounds in toluene in the presence of POCl3 and P2O5 Bischler-Napieralski cyclization occurs giving 1-(1-aryl-5-methyl-1H-1,2,3-triazol-4-yl)-4,9-dihydro-3H-β-carbolines that can be transformed into β-carboline and tetrahydro-β-carboline derivatives. 相似文献
19.
Josephine Michael Steven B. Larson Morteza M. Vaghefi Roland K. Robins 《Journal of heterocyclic chemistry》1990,27(4):1063-1071
The syntheses of 3-amino-4-methyl-1-(β-D-ribofuranosyl)-1,2,4-triazolin-5-one ( 8a ) and its 2′-deoxy analog 8b as well as 5-amino-2-methyl-1-(β-D-ribofuranosyl)-1,2,4-triazolin-3-one ( 12 ) have been accomplished. Compounds 8a and 8b were synthesized via glycosylation of 3-bromo-5-nitro-1,2,4-triazole which was followed by replacement in three steps of the 3-bromo function to yield 3-nitro-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1,2,4-triazolin-5-one ( 4a ) and its 2′-deoxy analog 4b . Compounds 4a and 4b were methylated at N2, hydrogenated and deblocked to give 3-amino-4-methyl-1-(β-D-ribofuranosyl)-1,2,4-triazolin-5-one ( 8a ) and the 2′-deoxy analog 8b . Compound 12 was synthesized by glycosylation of 3-amino-1-methyl-1,2,4-triazolin-5(2H)-one ( 10 ). The structures of 8b and 12 were confirmed by single crystal X-ray diffraction analysis. 相似文献
20.
Abstract The transmannosylation activity of β-mannosidase from snail and β-galactosidase from Aspergillus oryzae was used for the synthesis of methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 1-hexyl, cyclohexyl, and 1-octyl β-D-mannopyranosides (3a-i), respectively. The regioisomeric specificities and wide substrate acceptance of this galactosidase are demonstrated. Thus, 4-nitrophenyl 4-O-(α-D-glucopyranosyl)-β-D-glucopyranoside (6), 4-nitrophenyl 2-O-(β-D-glucopyranosyl)-β-D-glucopyranoside (7), 4-nitrophenyl 2-deoxy-2N-acetyl-6-O-(2-deoxy-2-N-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside(8),4-nitropheny 13-O-(β-D-mannopyranosyl)-α-D-mannopyranoside (9), and 4-nitrophenyl 4-O-(β-D-mannopyranosyl)-β-D-mannopyranoside (10) were prepared by chemoenzymatic self-transfer reaction. 相似文献