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1.
In this work, two new effective methodologies have been adopted for the preparation of 5-(2′-bromobenzyloxy)pyrimidine-2,4-diones 6(a–k). In the first methodology, 5-hydroxy uracils 4(a–f) were alkylated with 2-bromobenzyl bromide 5a or 2-bromo-5-methoxy benzyl bromide 5b under phase transfer catalysis condition using lithium hydroxide/tetrabutyl ammonium bromide in N,N-dimethylformamide at 45 °C, and in the second method, the microwave irradiation (MWI) protocol has been exploited by mixing 5-hydroxy uracils 4(a–f) with 30 % excess of 2-bromobenzyl bromide 5a or 2-bromo-5-methoxy benzyl bromide 5b. A catalytic amount of TBAB and potassium carbonate was added and irradiated in an open Erlenmeyer flask in a microwave oven for 3–12 min. The tributyltin hydride-mediated radical cyclisation of 6(a–k) was carried out under MWI to generate 1H,3H,6H[2]benzopyrano[4,3-d]pyrimidine-2,4-diones 7(a–k) in 80–89 % yield, and the reaction time was shortened compared to the previously reported conventional radical cyclisation method. 相似文献
2.
A series of 5-(trifluoromethyl)-N-alkyl-1-(3-phenylisoquinoline-1-yl)-1H-pyrazole-4-carboxamides 4 has been effectively achieved in high yield and purity from the reaction of pyrazole carboxylic acid 2 with amines 3 in the presence of TBTU as a catalyst and diisopropyl ethylamine as a base in acetonitrile at room temperature. 相似文献
3.
Arim Woo Young Hoon Lee Shinya Hayami Leonard F. Lindoy Pierre Thu??ry Yang Kim 《Journal of inclusion phenomena and macrocyclic chemistry》2011,71(3-4):409-417
The interaction of the enantiopure (R)- and (S)-1-phenyl-N,N-bis(pyridine-3- ylmethyl)ethanamine ligands, R-L 1 and S-L 1 , with copper(II) chloride followed by addition of hexafluorophosphate resulted in the isolation of the corresponding enantiomeric complexes [Cu(R-L 1 )Cl](PF6) (1), [Cu(S-L 1 )Cl](PF6) (2) and [Cu(S-L 1 )Cl](PF6)??0.5Et2O (3), in which dimerization occurs through two long Cu??????Cl interactions, the ??-chloro bridges being thus strongly asymmetric. The organic ligand is bound to the metal centre via its N3-donor dipyridylmethylamine fragment in a planar fashion, such that each copper centre is in a square planar environment (or distorted square pyramidal with a long axial bond length if the additional interaction is considered). When R,S-L 1 was employed in a parallel synthesis, the similar racemic complex [Cu(R,S-L 1 )Cl](PF6)??0.5MeOH (4) was obtained, in which the L 1 ligands in each dimeric unit have opposite hands. In contrast to the complexes of L 1 , the reaction of Cu(II) chloride with the related ligand, (R)-1-cyclohexyl-N,N-bis(pyridine-3-ylmethyl)ethanamine (R-L 2 ), yielded the mononuclear complex [Cu(R,S-L 2 )Cl2] (5), displaying a distorted square pyramidal coordination geometry. The structure of this product along with its corresponding circular dichroism spectrum revealed that racemisation of the starting R-L 2 ligand has occurred under the relatively mild (basic) conditions employed for the synthesis. A temperature-dependent magnetic studies of the complexes 1, 2 and 5 indicate that a week ferromagnetic interaction is operative in each dicopper core in 1 and 2 with 2J?=?1.2?cm?1. On the other hand, a week antiferromagnetic intermolecular interaction is operative for 5. 相似文献
4.
V. M. Ostrovskaya V. V. Minin G. A. Zvereva A. V. Tsygankov N. N. Efimov D. A. Man’shev 《Russian Journal of Coordination Chemistry》2012,38(11):703-708
A number of reagent test papers were designed on the basis of redox indicators: copper(I) complexes with sheet polydentate 1-(2-carboxyphenyl)-5-heterylhydrazidinyl-6-celluloses (I?CIV) (heteryl = 6-methoxy-4-methylpyrimidin-2-yl, 4,6-dimethylpyrimidin-2-yl, benzoxazol-2-yl, and benzothiazol-2-yl). Complexes I?CIV were transformed under the action of H2O2 into copper(II) complexes with 1-(2-carboxyphenyl)-5-heterylformazanyl-6-celluloses (V?CVIII), respectively. When treated with Na2S, complexes V?CVIII were reversibly reduced to the starting copper(I) complexes I?CIV. The reactions were accompanied by bathochromic shifts from the central region of the visible spectrum to the higher wavelengths. Complex I was used to develop visual and reflectometric test methods for checking the peroxide content of pharmaceuticals and cosmetics at a level of 0.01% and above. 相似文献
5.
Prof. Dr. Otto Hromatka Dieter Binder Karl Eichinger 《Monatshefte für Chemie / Chemical Monthly》1975,106(2):555-558
The synthesis of 1-(3-thienyl)-benzimidazol-2-ones (3 a and4), described in an earlier paper1, has been further investigated. The Na-salt of3 a is converted to a benzimidazolone substituted in position 3 (3 b). Dehydrogenation of the thiophene nucleus of3 a with chloranil yields5 a, which undergoes substitution in position 3 with Cl(CH2)2N(CH3)2 to give5 b. Monochlorination of5 a yields5 c, the structure of which is confirmed by1H-NMR-spectroscopy.5 d is obtained by reaction of the Na-salt of5 c with Cl(CH2)2N(CH3)2. 相似文献
6.
Eman M. Flefel Waled A. Tantawy Randa E. Abdel-Mageid Abd El-Galil E. Amr Rolla Nadeem 《Research on Chemical Intermediates》2014,40(4):1365-1381
3-(Naphthalen-1-ylmethylene)-5-phenylfuran-2(3H)-one 1 was prepared and converted into a variety of heterocyclic systems of synthetic and biological importance. Benzylamine was reacted with furanone 1 to afford compounds 2 and 3 according to the reaction conditions. Butanamide 2 was reacted with thionyl chloride or thiourea to give derivatives 4 and 5, respectively. Compound 3 was reacted with ethyl cyanoacetate to give the corresponding pyrrolopyridine derivative 6. Treatment of 1 with hydrazine hydrate afforded compounds 7 and 8 according to the reaction conditions. Also, compound 1 was reacted with phenyl hydrazine, hydroxyl amine, malononitrile or thiourea to give compounds 9–12, respectively. Cyclization of 7 with ethoxymethylene-malononitrile, ethyl-(ethoxymethylene)cyanoacetate, carbon disulphide or acetylacetone afforded the corresponding compounds 13–16, respectively. Condensation of 7 with p-nitrobenzaldehyde gave the corresponding hydrazone 17, which was treated with thioglycolic acid or chloroacetyl chloride to give compounds 18 and 19, respectively. Also, most of the prepared products were tested for anti-avian influenza virus and revealed promising antiviral activity against H5N1 virus [A/Chicken/Egypt/1/2006 (H5N1)] by determination of both TC 50 and ED 50 and confirmed by plaque reduction assay on MDCK cells. Compounds 7, 8, 11, 12 and 13 showed the highest effect compared with the other tested compounds. 相似文献
7.
Hossein A. Dabbagh Alireza Najafi Chermahini 《Journal of the Iranian Chemical Society》2012,9(3):339-348
Stereoselective (exo-specific) synthesis, dynamic 1H NMR and computational analysis of exo-N??-{3-azatricyclo[3.2.1.0.2,4]oct-3-yl)mesithyloxy)methylene}-1-benzensulfunamide (3) were investigated. Aziridine nitrogen inversion gives rise to two sets of configurations where the N-substituent is Syn (S) or Anti (A) to C7 of the norbornyl ring. At lower temperature, the proton signals of aziridine exo-E-3 decoalesces to show two syn conformers and one anti conformer (exo-E-3 1 S ? $ \leftrightharpoons $ ?exo-E-3 2 S ? $ \leftrightharpoons $ ?exo-E-3 3 A ) with ratio of 60:20:20, respectively. Experimentally, the Gibbs free energy of activations [??G ? (kcal/mol) ?±?0.08] were calculated 11.96, 12.45 for 3 isomerizations. The standard Gibbs free energy (??G o kcal/mol) 0.174, 0, 0.174, and 0.298 at 213?K and energy minimum 6.64, 4.77 and 1.78 were calculated for 3 1S? $ \leftrightharpoons $ ?3 2S, 3 2S? $ \leftrightharpoons $ ?3 3 A , 3 1 S? $ \leftrightharpoons $ ?3 3 A isomerizations, respectively. The enthalpy (??H ?, kcal/mol) and entropy (??S ?, cal?mol?1?K?1) of activation for the nitrogen inversion of aziridine of 3 were calculated 11.2 and ?0.80, respectively. 相似文献
8.
Dr. Siegfried H. Weber Wolf Arnold Lucien H. Chopard-dit-Jean Marc Montavon 《Monatshefte für Chemie / Chemical Monthly》1975,106(2):491-497
The title compound (1) is hydrolysed at pH=0–2 to the new compounds 1-thiocarbamoyl-5-methyl-3.3-diphenylpyrrolidin-2-one (3) and the tetrahydrotriazine derivative (4). These compounds, together with 5-methyl-3.3.-diphenylpyrrolidin-2-imine (5), are the stable end-products of the reaction. The expected 5-methyl-3.3.-diphenyl-1-thiocarbamoyl-pyrrolidin-2-imine (6) is formed either as an intermediate or an end-product according to the conditions of hydrolysis. Its formation is analogous to that of the isomeric 5-methyl-3.3.-diphenyl-2-pyrrolidinylidene-thiourea (9) from 1-(N-methoxymethyl)-3-(5-methyl-3.3.-diphenyl)-2-pyrrolidinylidene)-thiourea (2) by cleavage of the methoxymethyl group. 相似文献
9.
Tianzhi Yu Shuxia Yang Yuling Zhao Peng Zhang Zhe Lv Duowang Fan Zhongrong Geng 《Research on Chemical Intermediates》2012,38(1):215-222
Three coumarin derivatives, 7-hydroxy-3-(2-pyridyl)coumarin (HPC), 7-(4-(5-(4-tert-butylphenyl)-1,3,4-oxadiazol-2-yl)benzyloxy)-3-(2-pyridyl)coumarin (Ox-PC), and 7-(4-(9H-carbazol-9-yl)butoxy)-3-(2-pyridyl)coumarin (Cz-PC), were synthesized and characterized by elemental analysis, 1H NMR, FT-IR, and UV?Cvis absorption spectra. The fluorescence behaviors of the compounds in methanol solutions and solid states were investigated. HPC exhibits weak green emission, whereas Cz-PC and Ox-PC show strong blue emissions in dilute solutions. 相似文献
10.
Sadiq-ur-Rehman Muhammad Aziz Choudhary Moazzam H. Bhatti Saqib Ali 《Journal of the Iranian Chemical Society》2012,9(1):35-45
A new series of di- and tri-organotin(IV) compounds with the general formula R4?n SnL n , where R?=?Me (1,2), Et (3), n-Bu (4,5), n-Oct (6), Ph (7) and L?=?(E)-3-(4-methoxyphenyl)-2-(4-chlorophenyl)-2-propenoate, were synthesized by reaction of silver salt of ligand or ligand acid with diorganotin dichloride/oxide and triorganotin chloride in 2:1 and 1:1 molar ratio, respectively. These compounds were characterized by elemental analyses, FT-IR, multinuclear (1H, 13C, 119Sn) NMR and mass spectrometry. The spectroscopic results revealed that all the diorganotin(IV) compounds possess trigonal bipyramidal structures in solution and octahedral geometry in the solid state around the tin atom. A linear polymeric trigonal bipyramidal structure in the solid state and a tetrahedral environment around the tin atom in non-coordinating solvents has been proposed for the triorganotin(IV) compounds. All synthesized compounds were tested in vitro against a number of microorganisms to assess their biocidal activity. These studies revealed that ligand acid and some of its organotin compounds show promising activity against different strains of bacteria and fungi but lowered than reference drugs. 相似文献
11.
Christof Kratky Wolfgang Reischl Elisabeth Altmann Erich Zbiral 《Monatshefte für Chemie / Chemical Monthly》1982,113(4):439-448
Oxidation of the α- and β-4-phenyl-1,2,4-triazolin-3,5-dione adducts of vitamin D3 (2 and1) withMCPBA yields two diastereomeric mixtures of the (5,10)-(7,8)-dioxiranes3 a,3 b,3 c and4 a,4 b respectively. The corresponding benzoates5 a,5 b,6 a and6 b were prepared and the X-ray crystal structure of5 b was determined. This analysis proved5 b to be the (5R, 1 OS)-(7R, 8R)-dioxirane of the β-resp. (6S)-4-phenyl-1,2,4-triazolin-3,5-dione adduct1 of vitamin D3. 相似文献
12.
Yasuko Saito Toshiyuki Takano Keita Sakakibara Hiroshi Kamitakahara Fumiaki Nakatsubo 《Cellulose (London, England)》2012,19(6):2105-2114
2,3-Di-O-myristyl-6-O-(zinc(II) phthalocyaninyl) cellulose (5) was synthesized from cellulose (1) by five reaction steps via 6-O-(3′,4′-dicyanophenyl)-2,3-di-O-myristyl cellulose (4). The key reaction was phthalocyanine-ring formation on a cellulose backbone, that is, the reaction of compound 4 with o-phthalodinitrile in the presence of hexamethyldisilazane and zinc acetate in DMF afforded to compound 5 in 35.4 % yield. Consequently, the degree of substitution with phthalocyanine moieties of compound 5 was 0.38. The LB monolayer film of compound 5 on an indium tin oxide (ITO) electrode was found to show photocurrent generation performance at 680 nm. 相似文献
13.
V. P. Zelenov A. A. Voronin A. M. Churakov Yu. A. Strelenko M. I. Struchkova V. A. Tartakovsky 《Russian Chemical Bulletin》2013,62(1):117-122
3-Amino-4-(tert-butyl-NNO-azoxy)furoxan (1a) and 4-amino-3-(tert-butyl-NNO-azoxy)-furoxan (1b) and their acetyl derivatives 6a,b were obtained. The equilibria 1a ai 1b and 6a ? 6b were studied. Furoxan 6b can undergo thermal rearrangement into 3-[(tert-butyl-NNO-azoxy)(nitro)methyl]-5-methyl-1,2,4-oxadiazole (7), prolonged heating of which gives N-(2-tert-butyl-5-nitro-1-oxido-2H-1,2,3-triazol-4-yl)acetamide (8). With the transformation 7 → 8 as an example, the possibility of participation of the azoxy group in the Boulton-Katritzky rearrangements was demonstrated for the first time. 相似文献
14.
Christine Ivancsics Prof. Dr. Erich Zbiral 《Monatshefte für Chemie / Chemical Monthly》1975,106(4):839-848
β-Cyanovinyl-triphenylphosphonium bromide (1) rearranges to (2-cyano-1-phenylethyl)diphenylphosphine oxide (2) on treatment with alkali.1 reacts with NaN3 to 5-triphenyl-phosphonium-1.2.3-triazole-ylide (3) and with cyclopentadiene to (5-cyano-bicyclo[2.2.1]hepten-2-yl-6)triphenylphosphonium bromide (4). Reaction of1 with thioamides leads to (α-cyano-β-amino-β-alkyl)-allyl-triphenylphosphonium hromides (6) together with [(2-alkyl-4-aminothiazolyl)-5-methyl]triphenylphosphonium bromides (5). (2-amino-3-imidazo[1.2—α]pyridinyl) methyl]triphenylphosphonium bromide (7) results from reaction of1 with 2-aminopyridine, [(2-amino-3-imidazo[1.2—α]pyrimidinyl)methyl]triphenylphosphonium bromides (8 and9) from 2-aminopyrimidine and 2-amino-4-6-dimethylpyrimidine resp. 相似文献
15.
Prof. Dr. O. Hromatka D. Binder K. Eichinger 《Monatshefte für Chemie / Chemical Monthly》1974,105(1):138-141
The synthesis of 5-(o-chlorophenyl)-7-trifluoromethyl-1H-thieno[3.2?e]-1.4-diazepin-2(3H)-one (10) starting from ethyl 3-amino-5-trifluoromethyl-2-thiophenecarboxylate (1) is described. 相似文献
16.
Tai Hasegawa Toschitake Iwamoto 《Journal of inclusion phenomena and macrocyclic chemistry》1988,6(2):143-156
The crystal structures of the four title compounds have been analyzed by single crystal X-ray diffraction methods at room temperature. Three with a general formula Cd[NH2(CH2)6NH2]Ni(CN)4·G (G=m-toluidine,Im;p-toluidine,Ip; and 2,4-xylidine,Ix) are the inclusion compounds of the respective aromatic molecules in the three-dimensional metal complex host (1,6-diaminohexane)cadmium(II) tetracyanonickelate(II). The remaining one is a coordination complex ofp-toluidine, bis(p-toluidine) (1,6-diaminohexane)cadmium(II) tetracyanonick-elate(II),II, Im, Ix, andII crystallize under similar experimental conditions;Ip is obtained using thep-toluidinemesitylene mixture at higher dilution than that used forII. Im crystallizes in the tri linic space group \(P\bar 1\) , witha=9.725(2),b=7.598(1),c=7.177(1) Å, α=90.44(1), β=98.80(1), γ=95.70(1)o, andZ=1 (the final conventionalR=0.037 for 3526 reflections);Ip: monoclinic,P2/m,a=9.540(2),b=7.611(1),c=7.120(1) Å, β=100.95(1)o, andZ=1 (R=0.027 for 1700 reflections);Ix: monoclinic,P2/m,a=9.628(2),b=7.613(1),c=7.122(1) Å, β=100.01(1)o, andZ=1 (R=0.049 for 2704 reflections);II: monoclinic,P21/n,a=12.107(3),b=10.117(2),c=12.471(3) Å, β=113.67(2)o, andZ=2 (R=0.037 for 2616 reflections). The structures ofIm, Ip andIx are similar to that of theo-toluidine inclusion compound of the same metal complex host. InII atrans pair of thep-toluidine molecules to the cadmium atom in the two-dimensional network formed by thecatena-μ-linkages of ?Cd?NH2(CH2)6NH2?Cd? and ?NC?Ni?CN?Cd?NC?Ni?CN?intersecting at each Cd atom; two cyanide groups of the tetracyanonickelate(II) moiety have free N-ends. 相似文献
17.
Shoji Matsumoto 《Tetrahedron letters》2007,48(7):1117-1120
The reaction of 2-(arylamino)-1-(methylthio)-1-tosylethenes (4) with hydrogen iodide in refluxing toluene gave 3-tosyl-2-(tosylmethyl)quinoline derivatives (6) in good yields. In this reaction, hydrogen iodide dose not only reductively removes the methylthio group of 4 to form an intermediary 1-(arylamino)-2-tosylethene (5), but also serves as a protic catalyst for the subsequent dimeric cyclization of 5 to lead to the quinoline derivatives (6). 相似文献
18.
Pyrolysis of the 3-O-allyl derivative 7 of isovanillin followed by alkylation of the derived allylphenol 8 afforded a series of benzaldehyde derivatives 9-11 each of which was transformed by initial treatment with methylmagnesium bromide followed by oxidation of the corresponding alcohols with activated manganese dioxide into a series of ketones 15-17. Palladium(0) catalysed isomerization of the double bond in the prop-2′-enyl side-chain afforded ketones 36-38 which were subjected to the Corey-Bakshi-Shibata asymmetric reduction protocol to afford the R-3-alkoxy-1-(1′-hydroxyethyl)-4-methoxy-2-(1″-propenyl) benzenes 42-44 in yields of approximately 60% and with ee's of 75%. 相似文献
19.
E. Vessally 《Journal of Structural Chemistry》2008,49(6):979-985
Energetic, geometric and magnetic criteria were applied to examine the stability and/or aromatic character for the cyclic molecules C 4 H 4 M (M = O, S, Se, Te, NH, PH, AsH and SbH) at B3LYP/6-311++G** and MP2/6-311++G** levels of theory. The isodesmic reactions and nuclear independent chemical shifts (NICS) calculations were utilized to examine the molecules for energetic and magnetic criteria, respectively. The isodesmic reaction energies reveal that thiophene (C 4 H 4 S, ?23.269 kcal/mol) and pyrrole (C 4 H 4 NH, ?20.804 kcal/mol) have the greatest aromatic stabilization energies and tellurophene (C 4 H 4 Te, ?15.114 kcal/mol) and stibole (C 4 H 4 SbH, ?1.169 kcal/mol) have the lowest aromatic stabilization energies in their corresponding groups at MP2/6-311++G**. The NICS calculations confirmed the results obtained through isodesmic reaction energies. 相似文献
20.
Palimécio G. Guerrero Jr. Paulo R. de OliveiraAdriano C.M. Baroni Francisco A. MarquesRicardo Labes Gabriela R. HurtadoMiguel J. Dabdoub 《Tetrahedron letters》2012,53(39):5302-5305
An efficient and novel total synthesis of the two bioactive retinoids temarotene and arotinoid acid (TTNPB) is described. The key steps in this process include the regio and stereoselective hydrotelluration of thioacetylene 9 and Te/Li transmetalation of mixed (Z)-1,2-bis(organylchalcogene)-1-alkene (Z)-3. The subsequent reaction involving the β-phenylthio vinyl lithiated intermediate 10 with dimethyl sulfate gave the (E)-vinyl sulfide 11. The Ni+2 cross-coupling of 11 with the corresponding phenylzinc bromide and p-oxazoline phenylzinc bromide 12 afforded the respective temarotene 2 and retinoid-oxazoline substituted 13. Finally, compound 13 was deprotected with HCl to furnish arotinoid acid (TTNPB) 1. 相似文献