共查询到20条相似文献,搜索用时 0 毫秒
2.
Maryam Ahmadian-Moghaddam Niels R. M. Reintjens Dr. Martin D. Witte Dr. Adriaan J. Minnaard 《European journal of organic chemistry》2023,26(20):e202300281
A reliable method is disclosed to introduce a fused methylene tetrahydrofuran ring into carbohydrates. The resulting bicyclic saccharides can be used as scaffolds in medicinal chemistry and drug design. In addition, the enol ether functionality serves as a handle that enables modification in biological systems via photoclick chemistry. The approach is based on the regioselective oxidation of the C-3 hydroxy group in gluco-configured pyranosides, followed by stereoselective indium-mediated allylation. The ring formation is induced by an iodocyclization reaction with a neighboring hydroxy group. Subsequent dehydrohalogenation affords the desired methylene-tetrahydrofuran-containing carbohydrates. 相似文献
3.
Karolina Ciesielska Marcin Hoffmann Maciej Kubicki Donata Pluskota-Karwatka 《Molecules (Basel, Switzerland)》2022,27(14)
A number of imines, including 12 new compounds, previously not reported in the literature, derived from variously fluorinated benzaldehydes and different anilines or chiral benzylamines were synthesized by a solvent-free mechanochemical method, which was based on the manual grinding of equimolar amounts of the substrates at the room temperature. In a very short reaction time of only 15 min, the method produced the expected products with good-to-excellent yields. The yields were comparable or significantly higher than those reported in the literature for the imines synthesized by other methods. Importantly, the conditions used for the reactions with aniline derivatives also resulted in the high yields of imines obtained from chiral benzylamines, and can be extended to the synthesis with other similar amines. Structures of all imines were confirmed by NMR spectroscopy: 1H, 13C and 19F. For four compounds, X-ray structures were also obtained. The synthetic approach presented in this paper contributes to the prevention of environmental pollution and can be easily extended for larger-scale syntheses. The mechanochemical solvent-free method provides a convenient strategy particularly useful for the preparation of fluorinated imines being versatile intermediates or starting material in the synthesis of drugs and other fine chemicals. 相似文献
4.
José Fuentes Mota Fernández José M. García Carmen Ortiz Mellet Pradera Adrián M. Angeles Tomasa Cuevas Lorite 《Journal of carbohydrate chemistry》2013,32(6):837-851
ABSTRACT The syntheses of N-hetaryl (thiazole-2-yl, 2-thiazoline-2-yl, 4,4-diphenyloxazoline-2-yl, cis-3a,4,5,6,7,7a-hexahydrobenzoxazole-2-yl)-N′-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl) thioureas (1a-1d), N-hetaryl (2-thiazoline-2-yl, 4,4-diphenyloxazoline-2-yl)-N′-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl) thioureas (2b, 2c) and 1,2,3,4,6-tetra-O-acetyl-2-deoxy-2-[3-(4′, 4′-diphenyl-2′-y1) thioureido]-β-D-glucopyranose (3c) are described. The structures and conformational properties of prepared compounds are based on analytical and spectroscopic (UV, IR, NMR and MS) data. 相似文献
5.
Chiral spiroacetals of the 1,7-dioxaspiro[5.5]undecane, 1,6-dioxaspiro[4.5]decane, and 1,6-dioxaspiro[4.4]nonane types have been prepared from carbohydrates in pyranose or furanose forms. The spirocyclization reaction has been accomplished from a conveniently homologated carbohydrate by an intramolecular hydrogen abstraction reaction promoted by alkoxy radicals. Thus, 2,3,4,6-tetra-O-benzyl-1-deoxy-1-(3'-hydroxypropyl)-alpha-D-glucopyranose (2) was photolyzed with visible light in the presence of (diacetoxyiodo)benzene and iodine to give a mixture of (1R)-(3) and (1S)-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose-1-spiro-2'-tetrahydrofuran (4). The photolysis of methyl 6-deoxy-6-(2'-hydroxyethyl)-2,3,4-tri-O-methyl-alpha-D-glucopyranoside (8) gave the isomeric spiroacetals methyl (5S)- (9) and (5R)-6-deoxy-5,2'-epoxy-6-ethyl-2,3,4-tri-O-methyl-alpha-D-glucopyranoside (10) in which the spirocenter is now located at C-5. The spiroacetals of the [5.5]undecane series: methyl (5R)- (19) and (5S)-6-deoxy-5,3'-epoxy-2,3,4-tri-O-methyl-6-propyl-beta-D-glucopyranoside (20) have been prepared starting from methyl 6-deoxy-6-(3'-hydroxypropyl)-2,3,4-tri-O-methyl-beta-D-glucopyranoside (18). The reaction has also been applied to hexofuranoses and 1-deoxy-1-(3'-hydroxypropyl)-2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose (21) gave rise to (1S)- (22) and (1R)-1-deoxy-2,3:5,6-di-O-isopropylidene-D-mannofuranose-1-spiro-2'-tetrahydrofuran (23); and 1-deoxy-1-(4'-hydroxybutyl)-2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose (28) to (1R)- (30) and (1S)-1-deoxy-2,3:5,6-di-O-isopropylidene-D-mannofuranose-1-spiro-2'-tetrahydropyran (32). Both spiroacetal enantiomers are formally available from the same carbohydrate. 相似文献
6.
7.
Synthesis of New Fluorinated Podophyllotoxin Derivatives 总被引:4,自引:0,他引:4
XueYingHE TianYI YanGuangWANG 《中国化学快报》2004,15(2):131-134
Five fluorinated podophyUotoxin derivatives were synthesized using dimethylamino-sulfurtrifluoride (DAST). 相似文献
8.
本工作利用CuCl/HOC2H4NH2催化剂,将1,2-二溴四氟乙烷与烯基有机硅化合物进行加威反应,制备了一系列新的含氟有机硅化合物,并进行了分析鉴定。对影响反应的诸因素做了初步探讨。 相似文献
9.
10.
Tomáš Bříza Martin Havlík Bohumil Dolenský Zdeněk Kejík Pavel Martásek 《Supramolecular chemistry》2013,25(3):237-242
Highly functionalized fluorinated porphyrins were synthesized by a convergent strategy. Nucleophilic substitution using fluorinated branched unit and 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin afforded highly functionalized fluorinated porphyrin 8 containing 24 fluorinated chains in the peripheral region. 相似文献
11.
12.
13.
W. J. Middleton Diana Metzger Karen B. Cunningham C. G. Krespan 《Journal of heterocyclic chemistry》1970,7(5):1045-1049
4-Amino-2,2,5,5-tetrakis(trifluoromethyl)-3-oxazoline ( 3a ) was prepared from the reaction of sodium cyanide with hexafluoroacetone and hexafluoroacetone imine, and from the reaction of hexafluoroacetone cyanohydrin with the imine. Several other oxazolines were also prepared by related reactions of other fluoroketones and imines. The proton nmr spectrum of an 15N-labeled sample of 3a shows that it exists in solution primarily as the amino tautomer and not as the imino tautomer 3b . Comparison of 3a with the closely related, pharmacologically active 4-amino-2,2,5,5-tetrakis(trifluoromethyl)-3-imidazoline ( 2 ) has shown large differences in ΔH of complex formation and reactivity with electrophilic reagents. 相似文献
14.
Direct: olefinations on one hand in comparison to eliminations of aldols cf various uloses on the other each proved to be specific as to the sice of unsaturation in the branched-chain products, found to be interconvertible with one exception under a variety of conditions. Although shown to be generally equivalent to its Witcig-counterpart:, the Peterson reagent employed is liable to cause eliminations in the initial olefin. One of the branched-chain products appears to be of unusual molecular rigidity as evidenced by a large 5J coupling. 相似文献
15.
H. Selig K. Kniaz G.B.M. Vaughan J. E. Fischer A. B. Smith 《Macromolecular Symposia》1994,82(1):89-98
The existence of the fully fluorinated fullerene, C60F60, is still subject to controversy. Mass spectrometric evidence shows that it exists, albeit in trace amounts five orders of magnitude in concentration below the most abundant C60F40-42. Generally, mixtures of C60Fn are obtained where n ranges from 30 to 52, depending on fluorinating conditions. The species with n = 36 is particularly stable. Attempts to increase n by use of the strongly fluorinating halogen fluorides, ClF3 or BrF5, have led to products C60FXXyOz (X = Br or Cl), where the origin of the oxygen is probably hydrolysis during analysis. Fluorinated C60 crystallizes as a mixture of hexagonal close packed (40%) and face-centered cubic (60%) phases. X-ray analysis yields an average C-F bond length of 1.49A. Fluorination of C70 leads to mixtures with maximum average stoichiometries of C70F52. 相似文献
16.
17.
通过两步法实现了1,4双-(1,4二-氨基)苯氧基苯(TPEQ),4,4二-氨基二苯醚(ODA)和4,4′-六氟亚异丙基-邻苯二甲酸酐(6FDA)的三元共聚,所得共聚物(PAA)经高温法或化学法脱水环化得对应的可溶性含氟聚酰亚胺(PI)。通过粘度,DSC,TG和1H NMR等分析数据比较了其综合性能。对PI的研究结果表明,化学法的粘度一般高于高温法,所有的PI均具有良好的溶解性和耐热性;不仅溶于DMF,还能很好的溶于CHC l3和THF,有效地改善了其加工性能;Tg>227℃,热损失5%的温度多在488℃以上,m.p.>550℃。其中PI3具有最好的综合性能,粘度1.065 dL.g-1,Tg 241.7℃,热损失5%的温度488℃,m.p.557.9℃,拉伸强度108.81MPa。 相似文献
18.
《Journal of fluorine chemistry》1986,32(2):229-231
The reinvestigation of acylation reactions of fluorinated aryl methylketones with ethyl esters at 0°C afforded fluorinated 1, 3-diketones in excellent yields. 相似文献
19.
20.