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1.
Sukanta KamilaEdward R. Biehl 《Tetrahedron letters》2012,53(31):3998-4003
(5Z,5′Z)-3,3′-(1,4-Phenylenebis(methylene)-bis-(5-arylidene-2-thioxothiazolidin-4-one) derivatives (5a-r) have been synthesized by the condensation reaction of 3,3′-(1,4- or 1,3-phenylenebis(methylene))bis(2-thioxothiazolidin-4-ones) (3a,b) with suitably substituted aldehydes (4a-f) or 2-(1H-indol-3-yl)2-oxoacetaldehydes (8a-c) under microwave conditions. The bis(2-thioxothiazolidin-4-ones) were prepared from the corresponding primary alkyl amines (1a,b) and di-(carboxymethyl)-trithiocarbonyl (2). The 2-(1H-indol-3-yl)-2-oxoacetaldehydes (8a-c) were synthesized from the corresponding acid chlorides (7a-c) using HSnBu3. 相似文献
2.
Shuo Qiao 《Journal of organometallic chemistry》2011,696(14):2746-2753
Reaction of quinolin-8-amine with 1H-pyrrole-2-carbaldehyde or 5-tert-butyl-1H-pyrrole-2-carbaldehyde catalyzed by HCO2H forms N-((1H-pyrrol-2-yl)methylene)quinolin-8-amine (≡ HL, 3a) or N-((5-tert-butyl-1H-pyrrol-2-yl)methylene)quinolin-8-amine (≡ HL′, 3b). Treatment of 3a and 3b respectively with AlMe3 or AlEt3 in toluene affords corresponding aluminum complexes LAlMe2 (4a), L′AlMe2 (4b) and LAlEt2 (4c). Reaction of 3a and 3b with an equivalent of ZnEt2 in toluene generates L2Zn and L′2Zn, respectively. A related compound N-((1H-pyrrol-2-yl)methylene)-2-(3,5-dimethyl-1H-pyrazol-1-yl)benzenamine (≡ HL″, 7) was prepared by reaction of 2-(3,5-dimethyl-1H-pyrazol-1-yl)benzenamine with 1H-pyrrole-2-carbaldehyde in the presence of HCO2H. Reaction of 7 with AlMe3 gives L″2AlMe (8), and with ZnEt2 yields L″2Zn (9). All new compounds were characterized by NMR spectroscopy and elemental analysis. The structures of complexes 4b, 5b and 8 were additionally characterized by single crystal X-ray diffraction analyses. Complexes 4a-4c, and 8 were proved to be active catalysts for the ring-opening polymerization (ROP) of ?-caprolactone (?-CL) in the presence of BnOH. The kinetic study of the polymerization reactions catalyzed by 4a and 8 was performed. 相似文献
3.
Christopher D. Gabbutt B. Mark Heron Carley Poyner Peter N. Horton 《Tetrahedron》2006,62(47):10945-10953
The oxidation of 3-[bis-(diaryl)methyl]chromones 2 with p-chloranil affords novel acetals, 3-[bis-(diaryl)methylene]-2-methoxychroman-4-ones, 4 through interception of a pyrylium type intermediate. Oxidation of 3-(2-hydroxyphenyl)-4-[bis-(diaryl)methyl]pyrazoles 8, derived from 2 and hydrazines, gave 4,4-diarylbenzopyrano[4,3-c]pyrazoles 15. The electronic absorption spectra of 4 and 15 upon protonation are comparable with those of triarylmethine cationic dyes. 相似文献
4.
Sergey S. Patrushev Tatyana V. Rybalova Igor D. Ivanov Valentin A. Vavilin Elvira E. Shults 《Tetrahedron》2017,73(19):2717-2726
The eudesmane-type methylene lactones (isoalantolactone, alantolactone, 4,15-epoxyisoalantolactone, 2′,2′-dichloro-4H-spiro[cyclopropane-1′,4-eudesma-11(13)-en-8β,12-olide], and alantolactone) react with 8-bromoxanthines (8-bromocaffeine, 8-bromotheobromine, 8-bromo-3-butyltheobromine, 8-bromotheophylline, 8-bromo-9-butyltheophylline) under Heck reaction conditions to produce the target (E)-13-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)eudesma-4(15),11(13)-dien-8β,12-olides and the subsequent endocyclic isomers - 11-(2,6-dioxo-2,3-dihydro-1H-purin-8-yl)-13-normethyleudecma-4(15)-7(11)-dien-8α,12-olides. It was revealed that the yield and product ratio depends on the reaction conditions and the structure of methylene lactone. The effectiveness of Pd(OAc)2–caffeine catalytic system has been demonstrated in this reaction. The electric eel acetylcholinesterase inhibitory activity of the eudecmanolide-xanthine hybrids was evaluated. Among the new type bisheterocycles compound 27 with butyl and 2-oxodecahydronaphtho[2,3-b]furan-3(2H)-ylidene)methyl substituents at C-7 and C-8 of the xanthine core showed moderate activity with IC50 value of 40 μM. 相似文献
5.
8 Phenyl- (2) and 8,8 diphenyl-heptafulvenes (3) have been synthesized and fully characterized. The 220 MHz NMR data on 2 and 3, as well as the 13C NMR data on 3, indicates only a small contribution of the dipolar structure for this system. The electrophilic and nucleophilic reagents react at different sites of this system while protonation of 2 and 3 occurs at the exocyclic methylene carbon butylation occurs at the 7 -membered ring, i.e. the 1- and 3-positions of 2 and only at the 3-position of 3, when treated with n-BuLi. Cycloaddition with tetracyanoethylene gives the [8 + 2]-cycloadduct for 2 and the [4 + 2] adduct for 3. 相似文献
6.
Four new meroterpenoids identified as (R)-4-((2,2-dimethylchroman-6-yl)methyl)-3-(4-hydroxyphenyl)-5-methoxyfuran-2(5H)-one (1), 1-(2,2-dimethylchroman-6-yl)-3-(4-hydroxyphenyl)propan-2-one (2), (R,E)-3-(2,2-dimethylchroman-6-yl)-4-hydroxy-5-((2-(2-hydroxypropan-2-yl)-2,3-dihydrobenzofuran-5-yl)methylene)furan-2(5H)-one (3), methyl (R)-2-(2-(2-hydroxypropan-2-yl)-2,3-dihydrobenzofuran-5-yl) acetate (4), along with nine known compounds (5–13) were isolated from a chemical-epigenetic culture of Aspergillus terreus OUCMDZ-2739 with 10 μM trichostatin A (TSA). Under the same condition without TSA, A. terreus OUCMDZ-2739 produced different compounds (14–20), supporting that the chemical-epigenetic modification of fungi could enrich the chemodiversity of the fungal products. The cytotoxicity was observed for compound 8 against K562 cell, 9 against MCF-7 and K562 cells and 12 against MCF-7 cell with IC50 values of 9.5, 10.1, 13.0 and 8.5 μM, respectively. Compounds 3, 8 and 17 exhibited stronger α-glucosidase inhibition than 1-deoxynojirimycin and acarbose (positive controls) with IC50 values of 24.8, 1.2, 61.6, 191.7 and 555.1 μM, respectively. The enzyme kinetics study further indicated that compound 8 was an anticompetitive inhibitor with Ki value of 1.42 μM. 相似文献
7.
《Arabian Journal of Chemistry》2019,12(8):2721-2731
Two series of novel bis(indole) analogues viz., N′-((5-substituted-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)alkanehydrazides (7a–f) and N′-((5-substituted-1-(3-methylbut-2-enyl)-1H-indol-3-yl)methylene)-n-(1H-indol-3-yl)acetohydrazide (8a–f) were synthesized and characterized by spectral analysis. The target molecules were screened for their antimicrobial, anticancer activities and structure and activity relationship (SAR) was investigated. Compounds 7a, 7c and 8a were found to be active in antimicrobial screening. Anticancer screening reveals that Compound 7c was active against HeLa cell line with an IC50 of 43.1 μM and compound 7d was found to be interesting candidate with an IC50 of 26.0 and 30.2 μM against Colo-205 and Hep G2 cell lines respectively. 相似文献
8.
The syntheses of seven flexible bidentate bis-pyridyl diamide and four monodentate pyridyl amide ligands containing central amide units are described. The bis-pyridyl ligands were prepared in one step from commercially available compounds in moderate to good yield. These compounds all possess external metal coordinating pyridyl groups and internal amide functionalities, with the potential to bind anions. Crystal structures of six of the bis-pyridyl diamide ligands are described. The four compounds with xylene cores N,N′-[1,3-phenylenebis(methylene)]bis-3-pyridinecarboxamide 1, N,N′-[1,3-phenylenebis(methylene)]bis-4-pyridinecarboxamide 2, N,N′-[1,4-phenylenebis(methylene)]bis-3-pyridinecarboxamide 3 and N,N′-[1,4-phenylenebis(methylene)]bis-4-pyridinecarboxamide 4 crystallize with extensive amide N-H?OC hydrogen bonding between the diamide compounds, giving rise to two and three dimensional hydrogen bonded networks. N,N′-Bis(3-pyridylmethyl)benzene-1,3-dicarboxamide 5, the only compound with the amide groups directly attached to a central benzene core, was not able to be crystallised. N,N′-2,6-Bis(3-pyridylmethyl)pyridine dicarboxamide 6 and N,N′-2,6-bis(4-pyridylmethyl)pyridine dicarboxamide 7 have a mismatch of hydrogen bond donor and acceptor regions preventing ready involvement of the amide NH groups in network formation. For comparison we also prepared compounds N,N′-2′-propyl-6-(3-pyridylmethyl)pyridine dicarboxamide 10 and N,N′-2′-propyl-6-(4-pyridylmethyl)pyridine dicarboxamide 11 with two amide groups but only the one external donor pyridyl moiety, and compounds N-6-[(3-pyridylmethylamino)carbonyl]-2-pyridinecarboxylic acid methyl ester 8 and N-6-[(4-pyridylmethylamino)carbonyl]-2-pyridinecarboxylic acid methyl ester 9, which have only the one amide. 相似文献
9.
Wittig homologation of 2-(chloromethyl)-2H-chromen-2-ol derivatives 2a–t with (ethoxycarbonylmethylene)triphenylphosphorane provided the 2-oxoethylidene-2,3-dihydrobenzoxepine-4-carboxy-lates 3a–t with Z (cis) selectivity. Various basic catalysts were studied for the reaction of 2-(chloromethyl)-2H-chromen-2-ol 2a with the combination of Wittig reagent to provide compound 3b. The reaction of 2-(chloromethyl)-2H-chromen-2-ol 2a with other Wittig reagents, such as methylene(triphenylene)phosphorane and (1-ethoxycarbonylethylidene)triphenylphosphorane provided ketone derivative 4a rather 2-oxoethylidene derivative 3b. The ketone derivative 4a was reacted with Wittig reagent (ethoxycarbonylmethylene)triphenylphosphorane to give 2,3-dihydrobenzoxepine-4-carboxylate 3b. The present approach is novel, straight forward and being reported for the first time. 相似文献
10.
In the present study, via reaction of Ni(NO3)2·6H2O with two flexible dicarboxylic ligands under the solvothermal reaction conditions, two new Ni(II)-containing coordination complexes with the chemical formulae of [Ni4(L1)4(DMF)4·2DMF]n (1) and [Ni(L2)(DMF)]n (2) (H2L1= 2,2'-(1,4-phenylenebis(methylene))bis(sulfanediyl)dinicotinic acid and H2L2 ?= ?2,2'-(1,2-phenylenebis(methylene))bis(sulfanediyl)dinicotinic acid) have been prepared. For the treatment of the gastric carcinoma, the Cell Counting Kit-8 kit was carried out for the detection of the gastric carcinoma cells viability after compound treatment. Additionally, the Annexin V-FITC/PI apoptosis assay was also conducted and the apoptosis levels of the gastric carcinoma cells were determined after compound exposure. 相似文献
11.
The chemical reactivity of electron deficient chromone–linked acrylonitrile [3-(6-methylchromonyl)acrylonitrile (1)] was studied towards some active methylene nitriles and active methylene ketones. Reaction of compound 1 with malononitrile, cyanoacetamide, ethyl cyanoacetate, malononitrile dimer and acetoacetanilide afforded 5-cyanomethylchromeno[4,3-b]pyridines 2–4 and 9. Compound 1 reacted with 1H-benzimidazol-2-ylacetonitrile producing pyrido[1,2-a]benzimidazole derivative 5. Benzonitrile derivatives 6–8 were efficiently synthesized from the reaction of compound 1 with acetylacetone, ethyl acetoacetate and diethylmalonate. In these reactions a diversity of products has been synthesized through a domino process, including Michael addition, retro-Michael with γ-pyrone ring opening followed by different types of recyclization (RORC). Structures of the new synthesized products were deduced on the basis of their analytical and spectral data, and the reaction mechanisms are discussed. 相似文献
12.
Electrophilic attack of the active methylene group in 3-methyl-1-phenyl-5-pyrazolone (2) by s-triazine (1) leads to aminomethinylation of 2 with formation of 3-methyl-1-phenyl-4-aminomethylene-5-pyrazolone (4). Subsequent interaction of 4 with 2 explains the formation of 4,4′-methenyl-bis-[3-methyl-1-phenyl-5-pyrazolone (5). 1-Phenyl-3,5-pyrazolidinedione (6) reacts analogously with 1 forming 1-phenyl-4-aminomethylene-3,5-pyrazolidinedione (7). N,N′-Bis-indanyl-formamidine (9) results from the interaction of 2-amino-indane (8) with 1. 相似文献
13.
Uroš Urši? 《Tetrahedron》2010,66(24):4346-1445
(2E,3Z)-2-(1-Methyl-2,5-dioxoimidazolidin-4-ylidene)-3-[(arylamino- or heteroarylamino)methylene]succinate 5 obtained by [2+2] cycloaddition of (5Z)-5-[(dimethylamino)methylene]-3-methylimidazolidine-2,4-dione (1) and dimethyl acetylenedicarboxylate (2) followed by substitution of the dimethylamino group with aromatic or heteroaromatic amines, afforded by heating in ethanol in the presence of potassium hydroxide, potassium salts 6. Acidification of 6 with hydrochloric acid afforded mixtures of (E)- and (Z)-isomers of methyl 4-(2-hydroxy-1-methyl-5-oxo-1H-imidazol-4(5H)-ylidene)-5-oxo-1-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates. On the other hand, alkylation of compounds 6 with methyl iodide or benzyl bromide produced the corresponding methyl (E)-4-(2-methoxy- or 2-benzyloxy-1-methyl-5-oxo-1H-imidazol-4(5H)-ylidene)-5-oxo-1-phenyl-4,5-dihydro-1H-pyrrole-3-carboxylates 9, derivatives of a new triazafulvalene system. 相似文献
14.
(+)-ε-Cadinene (1) and (-)-γ2cadinene (2) have been synthesized from the enol ether ketone 3 via the methylene ketone 4. These two stereospecific total syntheses confirm the structures assigned to these sesquiterpenes and represent the first preparation by totally synthetic methods of any of the widespread group of cadinanes in their native state. 相似文献
15.
《Arabian Journal of Chemistry》2020,13(1):545-556
A new series of 4-((4,4-dimethyl-2,6-dioxocyclohexylidene)methylamino)-N-(substituted)benzenesulfonamide 3–17, monosubstituted 2-((4-((4-aminophenyl)sulfonyl)phenyl)amino)methylene 18, and its disubstituted derivative 19 were synthesized from the starting material 2-((dimethylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione 2. The crystal structures of compounds 2, 7 and 13 were reported by us through X-ray crystallography. All the prepared compounds were evaluated for their antibacterial activity against Gram-positive bacteria (Staphylococcus aureus, Bacillus subtilis, Clostridium sporogenes), Gram-negative bacteria (Pseudomonas aeruginosa, Escherichia coli), and antifungal activity against Aspergillus fumigatus, Penicillium chrysogenum, Fusarium oxysporum, Candida albicans. The synthesized compounds displayed interesting antimicrobial activity. Compounds 4 and 12 were the most potent in this study and displayed higher activity compared to the reference drugs, with MIC value of 3.9–31.3 μg/mL against a panel of Gram-positive, Gram-negative bacteria and fungi. Molecular modeling was performed inside the active site of dihydropteroate synthase. The synthesized compounds showed similar orientation and binding interactions to that of the co-crystallized ligand inside the binding pocket. 相似文献
16.
2 - Aminobenzimidazolyl - 1 - phenylimidate 1; 1 - cyan - 2 - aminobenzimidazole 5 and 2 - aminobenzimidazolyl - 1 - amidines 8 were synthesized. 1 and 8 give with aromatic aldehydes or acids 1,2 - dihydro - 3 - aryl - 4 - phenoxy(or amino) - s - triazino[1,2-a]- or 2 - aryl - 4 - phenoxy(or amino) - s - triazino[1,2-a] - benzimidazoles 3, 3a, 4, 4a. 5 gives with isocyanates or azomethines tetrahydro - s - triazino[1,2-a] - benzimidazoles 6 and 7. The mass- and IR-spectres of the synthesized compounds are discussed. 相似文献
17.
P. Praveen Kumar Y. Dathu ReddyCh. Venkata Ramana Reddy B. Rama DeviP.K. Dubey 《Tetrahedron letters》2014
Green and efficient one pot, three-component synthesis of novel 2-amino-6-(1,4-dioxo-3,4-dihydrophthalazin)-2(1H)-yl-4-phenyl-4H-pyran-3,5-dicarbonitriles 6 has been developed by condensing 3-(1,4-dioxo-3,4-dihydrophthalazin-(1H)-yl)-3-oxopropanenitrile 3, benzaldehydes 4 and active methylene compounds 5 using l-proline as catalyst in EtOH at RT. 相似文献
18.
Barbara Binotti Elisabetta Foresti Piera Sabatino Daniele Zuccaccia 《Journal of organometallic chemistry》2004,689(3):647-661
Complexes [Pd(η1, η2-5-OMe-C8H12)(N,O)]BF4 (N,O=2,6-(i-Pr)2(C6H3)NC(Ph)-C(Ph)O, 1; 2,6-(i-Pr)2(C6H3)NC(Me)-C(Ph)O, 2; 2-benzoylpyridine, 3) were synthesized by the reactions of [Pd(η1,η2-5-OMe-C8H12)Cl]2 with the suitable N,O-ligand. They were tested as catalysts for olefin or alkyne polymerizations. During such reactions 1-3 quantitatively transformed into their η1,η2-1-OMe-C8H12 isomers (1a-3a). The same isomerization occurred in methylene chloride, even in the absence of olefins or alkynes, with a much slower rate. All complexes were fully characterized in solution by multinuclear and multidimensional low temperature NMR spectroscopy. The solid state structures of complexes 1 and 1a were investigated by X-ray single crystal studies. 19F, 1H-HOESY NMR experiments carried out in methylene chloride-d2 at 217 K indicated that the anion prefers to locate on the side of N,O-ligand shifted toward the O-arm in 1-1a and 2-2a while it approaches the N-arm in 3 and 3a compounds. 相似文献
19.
By the reaction of cis- and trans-2-aminomethylcyclohexanol (1, 2), cis- and trans-2-hydroxymethyl-cyclohexylamine (3,4) and the homologous cycloheptane derivatives (5-8) with ethyl p-chlorobenzimidate (11), cis- and trans-5,6-tetramethylene- and pentamethylene-2,3,5,6-tetrahydro-4H-1,3-oxazines (12,13,16,17) and cis- and trans-4,5-tetramethylene- and pentaimethylene-4,5-dihydro-6H-1,3-oxazines (14, 15, 18, 19) were prepared. The amidine intermediate of the ring-closure reaction was isolated, and the mechanism of the acid-catalysed reaction is discussed. It follows from the 1H NMR data that in the preferred conformations of the cis-tetramethylene-tetrahydrooxazines the methylene group of the hetero ring is equatorial and the hetero atom (O or N) axial. In contrast, the conformation equilibria of the cis pentamethylene derivatives, in accordance with earlier X-ray analysis, are shifted towards the conformer containing the methylene group in isoclinal and the hetero atom in equatorial position. The preferred conformations 12a and 14a of the tetramethylene derivatives 12 and 14 were also determined by X-ray crystal analysis. 相似文献
20.
Grignard reaction of ethyl 3-(3,5-dimethoxyphenyl)-propionate (4) followed by cyclodehydration of the carbinol (5) with conc H2SO4 gave 4,6-dimethoxy-3,3-dimethylindane (6). Oxidation of the indane (6) with CrO3-pyridine complex in methylene chloride gave 4,6-dimethoxy-3,3-dimethylindan-1- one (1) in high yield. Conjugate addition of methyl magnesium iodide to methyl α-cyano-β-methyl-3,5-dimethoxycinnamate (11), prepared from 3,5-dimethoxyacetophenone (10) by Knoevenagel condensation, resulted in methyl 2-cyano-3-(3,5-dimethoxyphenyl)-3,3-dimethylpropionate (12). Refluxing the ester (12) with aq DMSO containing sodium chloride gave the corresponding nitrile (15) which underwent Höesch reaction to yield 5,7-dimethoxy-3,3-dimethylindan-1-one (2). 相似文献