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1.
A high-yield straightforward conversion of lactams to lactim ethers is shown by the conversion of (10H)-dipyrrin-1-ones to (11H)-dipyrrin-1-ol methyl and ethyl ethers in 90% yield from heating in neat trimethyl or triethyl phosphite at 160°C. Unlike
the parent dipyrrinones, which form intermolecularly hydrogen-bonded dimers in CHCl3, their lactim ethers are shown to be monomeric by vapor pressure osmometry. The latter react with boron trifluoride etherate
to N,N′-bridged BF2 derivatives that exhibit strong fluorescence (φF 0.6–0.8) near 535 nm. X-Ray crystal structures were obtained of the lactim ethyl ether of kryptopyrromethenone and the BF2 derivative of the lactim ethyl ether 2,3-diethyl-7,8-dimethyl-(10H)-dipyrrin-1-one. 相似文献
2.
A high-yield straightforward conversion of lactams to lactim ethers is shown by the conversion of (10H)-dipyrrin-1-ones to (11H)-dipyrrin-1-ol methyl and ethyl ethers in 90% yield from heating in neat trimethyl or triethyl phosphite at 160°C. Unlike
the parent dipyrrinones, which form intermolecularly hydrogen-bonded dimers in CHCl3, their lactim ethers are shown to be monomeric by vapor pressure osmometry. The latter react with boron trifluoride etherate
to N,N′-bridged BF2 derivatives that exhibit strong fluorescence (φF 0.6–0.8) near 535 nm. X-Ray crystal structures were obtained of the lactim ethyl ether of kryptopyrromethenone and the BF2 derivative of the lactim ethyl ether 2,3-diethyl-7,8-dimethyl-(10H)-dipyrrin-1-one.
Correspondence: David A. Lightner, Department of Chemistry, University of Nevada, Reno, Nevada 89557-0020 USA. 相似文献
3.
Tove Wiklund Susanne Olsson Anders Lennartson 《Monatshefte für Chemie / Chemical Monthly》2011,39(2):813-819
Abstract
The reaction between benzyllithium and prochiral 2-ethylpyridine in tetrahydrofuran has been studied. In the presence of N,N,N′,N′′,N′′-pentamethyldiethylenetriamine (PMDTA), it was found that 1-(2-pyridyl)ethyllithium was formed as a PMDTA complex. This complex is mononuclear, with lithium coordinated to the pyridyl nitrogen atom only; there are no short lithium–carbon distances and the structure approaches that of an enamide rather than a carbanion. The complex undergoes spontaneous resolution and forms chiral crystals with two molecules in the asymmetric unit; the two molecules have different configurations at the chirogenic pyridyl nitrogen atoms but share the same chiral conformation of the chelate ring systems. Reaction between benzyllithium and 2-ethylpyridine in tetrahydrofuran in the absence of PMDTA was found to give a high proportion of lithium 4-benzyl-2-ethyl-1,4-dihydropyridinide, and crystals of a dinuclear complex displaying tetrahydrofuran ligands and co-crystallised n-hexane molecules were isolated. 相似文献4.
Ingrida Tumosien? Zigmuntas Jonas Beresnevi?ius 《Monatshefte für Chemie / Chemical Monthly》2009,43(9):1523-1528
Abstract
Reaction of 3,3′-[(4-alkoxyphenyl)imino]bis(propanoic acid hydrazides) with CS2 in alkaline solution and subsequent acidification gave 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(1,3,4-oxadiazole-2(3H)-thiones). The same dihydrazides on reaction with phenyl isocyanates or phenyl isothiocyanates were converted to bis[N′-(phenylaminocarbonyl)propanoic acid hydrazides] and bis[N′-(phenylaminocarbonothioyl)propanoic acid hydrazides], which underwent cyclization in alkaline medium to produce 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(4-phenyl-2,4-dihydro-3H-1,2,4-triazol-3-ones) and their 3-thio analogues, whereas in sulfuric acid or POCl3 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(N-phenyl-1,3,4-oxadiazol-2-amines) and 5,5′-[[(4-alkoxyphenyl)imino]diethane-2,1-diyl]bis(N-phenyl-1,3,4-thiadiazol-2-amines) were obtained. 相似文献5.
Andrei V. Bogdanov Vladimir F. Mironov Lenar I. Musin Rashid Z. Musin Dmitry B. Krivolapov Igor A. Litvinov 《Monatshefte für Chemie / Chemical Monthly》2011,41(3):81-85
Abstract
The reaction of aminomethylisatins (isatin N-Mannich bases) with hexaethylphosphorous triamide leads to the formation of 1,1′-bis(dialkylaminomethyl)-3,3′-bis(indolin-3-ylidene)-2,2′-diones and 1,1′-bis(1,3-dioxo-1,3-dihydroisoindol-2-ylmethyl)-1H,1′H-[3,3′]bisindolylidene-2,2′-dione. 相似文献6.
A. V. Velikorodov O. Yu. Poddubnyi A. K. Kuanchalieva O. O. Krivosheev 《Russian Journal of Organic Chemistry》2010,46(12):1826-1829
1,3-Dipolar cycloaddition to methyl 4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)-1-oxoethyl]-phenylcarbamate of diazomethane in chloroform-diethyl ether and of 3,4-dimethoxybenzonitrile
oxide generated from the corresponding aldehyde oxime by the action of N-chlorobenzenesulfonamide sodium salt (Chloramine B) in boiling ethanol gave, respectively, methyl 4-(2-oxo-1′,5′-dihydro-1H-spiro[indole-3,4′-pyrazol]-3′-ylcarbonyl)phenylcarbamate and methyl 4-[3′-(3,4-dimethoxyphenyl)-2-oxo-1H,4′H-spiro[indole-3,5′-isoxazol]-4′-ylcarbonyl]phenylcarbamate. The condensation of methyl 4-[2-(2-oxo-2,3-dihydro-1H-indol-3-ylidene)-1-oxoethyl]phenylcarbamate with hydrazine hydrate in ethanol afforded methyl 4-(2-oxo-1,2,2′,4′-tetrahydrospiro[indole-3,3′-pyrazol]-5′-yl)phenylcarbamate. 相似文献
7.
A. V. Velikorodov N. M. Imasheva A. K. Kuanchalieva O. Yu. Poddubnyi 《Russian Journal of Organic Chemistry》2010,46(7):971-975
Condensation of methyl 4-acetylphenylcarbamate with isatin in the presence of diethylamine afforded methyl 4-[(3-hydroxy-2-oxo-2,3-dihydro-1H-indol-3-yl)acetyl]phenylcarbamate which was converted into the corresponding chalcone on heating in glacial acetic acid in
the presence of hydrochloric acid. 1,3-Dipolar cycloaddition to that chalcone of azomethine ylide generated from 2-phenacylisoquinolinium
bromide by the action of triethylamine gave methyl 4-(3′-benzoyl-2-oxo-1′,2,2′,3,3′,10b′-hexahydro-1H-spiro-[indole-3,1′-pyrrolo[1,2-a]isoquinolin]-2′-ylcarbonyl)phenylcarbamate. Condensation of 2-hydroxy- and 2,4-dihydroxybenzaldehydes with methyl 4-acetylphenylcarbamate
in the presence of gaseous hydrogen chloride resulted in the formation of chromenium salts with a methoxycarbonylaminophenyl
fragment on the C2 atom in the heteroring. 相似文献
8.
Mohammad Rahimizadeh Mehdi Pordel Mehdi Bakavoli Zahra Bakhtiarpoor Ala Orafaie 《Monatshefte für Chemie / Chemical Monthly》2009,20(2):633-638
Abstract
New imidazo[4,5-a]acridone derivatives were synthesized from the rearrangement of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles. New imidazo[4,5-a]acridines were obtained from the reaction of imidazo[4,5-a]acridones in boiling POCl3. All of these compounds exhibited antimicrobial activities comparable to streptomycin as reference drug. 相似文献9.
A. V. Velikorodov A. K. Kuanchalieva O. L. Titova 《Russian Journal of Organic Chemistry》2010,46(7):1060-1065
Oximation of indoles having a methoxycarbonylamino group on C5 and an acyl group on C3 with hydroxylamine hydrochloride in the presence of pyridine gave the corresponding oximes. The reduction of the 3-C=O group
with sodium tetrahydridoborate in the presence of sodium hydroxide was accompanied by removal of the methoxycarbonyl group
at the pyrrole nitrogen atom with formation of racemic alcohols. 1,4-Addition of 1-(pyridin-3-yl)butane-1,3-dione to dimethyl
1,4-benzoquinone diimine N,N′-dicarboxylate in dioxane in the presence of sodium methoxide, followed by heating in boiling 22% hydrochloric acid, afforded
methyl 2-methyl-5-(methoxycarbonylamino)-3-(pyridin-3-ylcarbonyl)-1H-indole-1-carboxylate. 3-(Dimethylamino)-1-(4-methyl-1,2,5-oxadiazol-3-yl)prop-2-en-1-one reacted with N,N′-bis(methoxycarbonyl)- and N,N′-bis(phenylsulfonyl)-1,4-benzoquinone diimines in methylene chloride and acetic acid, respectively, in the presence of BF3 · Et2O to produce indoles having a 1,2,5-oxadiazolylcarbonyl group on C3. 相似文献
10.
Solvothermal synthesis and structures of three novel heterometallic microporous coordination polymers assembled from 2-hydroxy-nicotinic acid 总被引:1,自引:0,他引:1
Hua Hong Zou Shu Hua Zhang Yu Xiao Chao Feng Yin Guang Wang 《Structural chemistry》2011,22(1):135-140
Abstract
Three novel heterometallic microporous coordination polymers {M(Hnico)3M′} n (1, M = Co, M′ = K; 2, M = Ni, M′ = K; 3, M = Co, M′ = Na, Hnico is the anion of 2-hydroxy-nicotinic acid, where the proton is transferred from the phenolate hydroxy group to the nitrogen atom of imine pyridine ring) were synthesized by hydrothermal reaction between M(Ac)2·4H2O, M′OH and a multifunctional organic aromatic H2nico ligand and characterized by IR spectrum, elemental analysis, raman spectrum and the single crystal X-ray diffractions. In complexes 1–3, the M2+ ions linked three different Hnico ligand formed [M(Hnico)3]− subunit which further interlinked the six-coordination M′+ cation constructed 3D network. The network topology of 1–3 can be simplified a rare 3D (4,4)-connected (41263) net. 相似文献11.
A. L. Kurlovich V. A. Tarasevich N. G. Kozlov 《Russian Journal of Organic Chemistry》2009,45(10):1503-1508
Condensation of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and cyclohexane-1,3-dione, methyl
2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone gave the corresponding 7-(2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydro-12H-benzo[c]acridin-8-ones. The reaction of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and indan-1,3-dione
produced 7-(2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-8H-benzo[h]indeno[1,2-b]quinolin-8-one. 7-(2′-Hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydrobenzo[b][1,10]phenanthrolin-8-ones were obtained by three-component condensation of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde
with quinolin-8-amine and cyclohexane-1,3-dione, methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone. 相似文献
12.
Senem Karahan Pelin Kose Elif Subasi Huseyin Alp Hamdi Temel 《Transition Metal Chemistry》2008,33(7):849-854
The hitherto unknown complexes, [M2(CO)6(μ-CO)(μ-L)], [M = Cr; 1, Mo; 2, W; 3] and [M2(CO)6(μ-CO)(μ-L′)], [M = Cr; 4, Mo; 5, W; 6] have been synthesized by the photochemical reactions of photogenerated intermediate, M(CO)5THF (M = Cr, Mo, W) with thio Schiff base ligands, N,N′-bis(2-aminothiophenol)-1,4-bis(2-carboxaldehydephenoxy)butane (H
2
L) and N,N′-bis(2-aminothiophenol)-1,7-bis(2-formylphenyl)-1,4,7-trioxaheptane (H
2
L′). The complexes have been characterized by elemental analysis, LC-mass spectrometry, magnetic studies, FT-IR and 1H NMR spectroscopy. The spectroscopic studies show that H
2
L and H
2
L′ ligands are converted to benzothiazole derivatives, L and L′ after UV irradiation and coordinated to the central metal as bridging ligands via the central azomethine nitrogen and sulphur
atoms in 1–6. 相似文献
13.
Murat Taş Seval Çamur Yalçın Kılıç 《Journal of Thermal Analysis and Calorimetry》2011,103(3):995-1000
The complexes were synthesized by the reaction between sodium salt of p-aminosalicylic acid (PAS) and Cu(II) for 1 and corresponding ethylenediamine (en) or its derivatives for 2–6. The complexes were characterized by using elemental analyses, FT-IR, UV–Vis, magnetic moment measurements, and thermal analyses
techniques. In complex 1[Cu2(PA)4(H2O)2], two Cu(II) ions were found as bridged by four μ-O:O′ p-aminosalicylato (PA) ligands, forming a cage structure, and two aqua ligands to form dinuclear square-pyramidal geometry
around Cu(II) ions. In the complexes 2–6, the PA (anionic form of p-aminosalicylic acid) coordinated to Cu(II) ions as monodentate manner by using its oxygen atom of deprotonated carboxylic
acid and ethylenediamine derivatives coordinated to the Cu(II) ions in bidentate manner to form mononuclear octahedral complexes
[Cu(PA)2(L)2] (L = ethylendiamine, N,N-dimethylethylendiamine, N,N′-dimethylethylendiamine, N,N,N′,N′-tetramethylethylendiamine, and 1,3-propanediamine, for complexes 2, 3, 4, 5, and 6, respectively). In all the complexes OH and NH2 groups of PA ligands were not coordinated to metals. 相似文献
14.
V. Ya. Sosnovskikh A. Yu. Sizov B. I. Usachev M. I. Kodess V. A. Anufriev 《Russian Chemical Bulletin》2006,55(3):535-542
Reactions of chromones with methyl ketoximes in the presence of lithium diisopropylamide follow the nucleophilic 1,2-addition
mechanism to give spiro[4H-chromene-4,5′-isoxazolines] in good yields. The isoxazoline ring in spiro[4H-chromene-4,5′-isoxazolines] undergoes opening under the action of conc. H2SO4, yielding α,β-unsaturated oximes. Their nitrosation and bromination lead to the corresponding spiroisoxazolines, while the
Beckmann rearrangement, to α,β-unsaturated amides. The latter are also formed directly from spiro[4H-chromene-4,5′-isoxazolines] under the action of PCl5. N-Substituted acetophenone hydrazones in the presence of lithium diisopropylamide react at the C(4) atom of 2-trifluoromethylchromone,
while acetophenone anil under the same conditions, at the C(2) atom.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 516–522, March, 2006. 相似文献
15.
Helio G. Bonacorso Cleber A. Cechinel Jussara Navarini Rosália Andrighetto Marcos A. P. Martins Nilo Zanatta 《Monatshefte für Chemie / Chemical Monthly》2011,21(6):277-285
Abstract
This work describes the regioselective synthesis of two new series of 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-4,5-dihydro-5-hydroxy-5-(trihalomethyl)-1H-pyrazoles], where the 3-substituents are H, Me, C6H5, 4-FC6H4, 4-ClC6H4, 4-BrC6H4, 4-NO2C6H4, 4,4′-BiPh, and 2-furyl, in a one-pot methodology with ethanol as solvent, from the reaction of 4-alkoxy-4-(alkyl/aryl/heteroaryl)-1,1,1-trihaloalk-3-en-2-ones with oxalyldihydrazide (51–89%). Complementarily, the dehydration reactions of five examples of the described oxalylbispyrazolines are also reported, which furnished the respective 1,1′-oxalylbis[3-(alkyl/aryl/heteroaryl)-5-(trihalomethyl)-1H-pyrazoles] in 53–78% yields without the two C(O)–N bond cleavages. 相似文献16.
Goran N. Kaluđerović Tanja M. Vasiljević Mila D. Laušević Akmal S. Gaballa Tibor J. Sabo 《Monatshefte für Chemie / Chemical Monthly》2009,140(5):553-557
Abstract The electrospray mass spectrometric (ESI–MS) behavior of the complexes trans-dichloro(ethylenediamine-N,N′-di-3-propionato)platinum(IV), trans-dibromo(ethylenediamine-N,N′-di-3-propionato)platinum(IV), dichloro(ethylenediamine-N,N′-di-3-propionic acid)platinum(II), tetrachloro(O,O′-di-n-butyl-ethylenediamine-N,N′-di-3-propanoate)platinum(IV), chlorotribromo(O,O′-di-n-butyl-ethylenediamine-N,N′-di-3-propanoate)platinum(IV), and dichloro(O,O′-di-n-butyl-ethylenediamine-N,N′-di-3-propanoate)platinum(II), with the formulae trans-[PtCl2(eddp)] (1), trans-[PtBr2(eddp)] (2), [PtCl2(H2eddp)] (3), [PtCl4(Bu2eddp)] (4), [PtBr3Cl(Bu2eddp)] (5), and [PtCl2(Bu2eddp)]·H2O (6), is reported. The deprotonated molecular ions or halide adducts are usually observed. ESI–MS data demonstrate the usefulness
of the method for efficient characterization of metal complexes in solution.
Graphical Abstract
相似文献
17.
Mahmood Tajbakhsh Moslem M. Lakouraj Majid S. Mahalli 《Monatshefte für Chemie / Chemical Monthly》2008,10(2):1453-1456
Various symmetrical dialkyl and diacyl disulfides are prepared easily in high yields from the corresponding alkyl and acyl
halides under mild and nonaqueous conditions using N,N′-dibutyl-N,N,N′,N′-tetramethyl-ethylenediammonium tetrahydroborate (BTMETB) or N,N′-dibenzyl-N,N,N′,N′-tetramethylethylenediammonium tetrahydroborate (BZTMETB) and elemental sulfur. The quaternary diammonium borohydrides were easily prepared by treatment of the corresponding quaternary
diammonium chloride or bromide with alkaline solution of sodium borohydride at room temperature. 相似文献
18.
V. A. Glushkov G. F. Krainova O. A. Maiorova V. I. Karmanov A. A. Gorbunov P. A. Slepukhin 《Russian Journal of Organic Chemistry》2012,48(4):575-581
Addition of 1,3,3-trimethyl-3,4-dihydroisoquinolines to N-benzylideneanilines gives substituted N-[2-(3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-1-phenylethyl]anilines, whereas 2′,5′,5′-trimethyl-4′,5′-dihydro-4H-spiro[naphthalene-1,3′-pyrrol]-4-one reacts with N-benzylideneanilines along two pathways involving cyclization to substituted 2,3,3a,4,10,11-hexahydrobenzo[f]pyrrolo[2,3-d]quinolin-5(1H)-ones or elimination of the aniline residue with formation of substituted 5′,5′-trimethyl-2-styryl-4′,5′-dihydro-4H-spiro[naphthalene-1,3′-pyrrol]-4-ones. 相似文献
19.
E. S. Denislamova N. V. Bubnov A. N. Maslivets 《Russian Journal of Organic Chemistry》2011,47(6):933-936
Methyl 1-aryl-3-benzoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione to give methyl 11-aryl-12-benzoyl-9-hydroxy-4,6-dimethyl-3,5,10-trioxo-4,6,8,11-tetraazatricyclo[7.2.1.02,7]dodec-2(7)-ene-1-carboxylates which underwent thermal recyclization to 1-aryl-3-benzoyl-4-hydroxy-1′,3′-dimethylspiro[pyrrole-2,5′-pyrrolo[2,3-d]pyrimidine]-2′,4′,5,6′(1H,1′H,3′H,7′H)-tetraones. 相似文献
20.
I. E. Tolpygin 《Russian Journal of Organic Chemistry》2012,48(1):104-108
A number of 2-(anthracen-9-yl)-substituted imidazolidines and hexahydropyrimidines were synthesized by reaction of N,N′-bis[aryl(hetaryl)methyl]ethylene-1,2-diamines and N,N′-bis[aryl(hetaryl)methyl]-propane-1,3-diamines with anthracene-9-carbaldehyde. The obtained compounds showed chemosensor
activity toward Cd2+, Cu2+, and Hg2+ ions. 相似文献