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1.
Mowafak Y. Shandala Mikdad T. Ayoub Mouayed J. Mohammad 《Journal of heterocyclic chemistry》1984,21(6):1755-1756
Ethyl β-methoxycrotonate I reacts with substituted carbonyl compounds II in benzene to give 4-methoxy-6-substituted-5,6-dihydro-2H-pyran-2-ones III. The reaction of IIIa and j with hydrazine hydrate in ethanol leads to 3-[(1′-thienyl-1-hydroxy)methyl]-5-hydroxy-1H-pyrazole (IVa) and 3-[1′-styryl-1′-hydroxy)methyl]-5-hydroxy-1H-pyrazole (IVj) in good yields. The structure of the products were assigned and confirmed on the basis of their elemental analysis and the electronic absorption, infrared and nmr spectra. 相似文献
2.
Brigitte Kopp Erika Kubelka Christian Reich Wolfgang Robien Wolfgang Kubelka 《Helvetica chimica acta》1991,74(3):611-616
Investigation of the tubers of Eranthis hyemalis (Ranunculaceae) afforded six chromenone glycosides. Their structures have been elucidated mainly by spectroscopic (FAB-MS, 2D-NMR techniques) and chemical methods (acidic and enzymatic hydrolysis) as 9-{[(β-D -glucopyranosyl)oxy]methyl}-8,11-dihydro-5-hydroxy-2-methyl-4H-pyrano[2,3-g][1]benzoxepin-4-one ( 1 ), 9-{[(β-D -gentiobiosyl)oxy]methyl}-8,11-dihydro-5-hydroxy-2-methyl-4H-pyrano[2,3-g][1]benzoxepin-4-one( 2 ), 9-{[(β-D -glucopyranosvl)oxy]melhyl}-8,11-dihydro-5-hydroxy-2-(hydroxy-methyl)-4H-pyrano[2,3-g][1]benzoxepin-4-one( 3 ), 8-{(2E)-4-[(β-D -glucopyranosyl)oxy]-3-methylbut-2-enyl}-5,7-dihydroxy-2-methyl-4H-1-benzopyran-4-one ( 4 ), 8-{(2E)-4-[(β-D -glucopyranosyi)oxy]-3-methylbut-2-enyl}-5,7-dihydroxy-2-(hydroxymethyl)-4H-1-benzopyran-4-one ( 5 ), and 7-{[(β-D -glucopyranosy1)oxy]methyl}-2,3-dihydro-2-(l-hydroxy-1-methylethyl)-4-methoxy-5H-furo[3,2-g][1]benzopyran-5-one ( 6 ). Compound 2 exhibited negative inotropic activity. 相似文献
3.
The treatment of ketosulfoxide 1 with phosgene in pyridine gave a mixture of 1-(4-hydroxy-8-methoxy-2-oxo-2H-1-benzopyran-3-yl)pyridinium hydroxide inner salt ( 4 ) and 7-methoxy-2-(methylthio)-3-(2H)benzofuranone ( 7 ). Ketosulfoxides 8 and 11 behaved similarly. The inner salt structure assigned to compounds 4, 10 , and 13 was confirmed by the unambiguous synthesis of 10 and 13 from hydroxycoumarins 15 and 18 . 相似文献
4.
James H. Looker Duane L. Shaneyfelt Wayne Halfar 《Journal of heterocyclic chemistry》1979,16(6):1281-1282
Condensation reactions of comenaldehyde methyl ether (I) with malonic acid, ethyl cyanoacetate, and cyanoacetamide to give β-(5-methoxy-4H-pyran-4-on-2-yl)acrylic acid (II), ethyl 2-cyano-3-(5-methoxy-4H-pyran-4-on-2-yl)propenoate (III), and 2-cyano-3-(5-methoxy-4H-pyran-4-on-2-yl)propenamide (IV), respectively, are described. Ultraviolet absorption spectra for 2-hydroxymethyl-5-methoxy-4H-pyran-4-one, I and II are presented. 相似文献
5.
David T. Connor Patricia A. Young Maximillian von Strandtmann 《Journal of heterocyclic chemistry》1978,15(1):115-117
The reaction of 1-methyl-3-(methylsulfinyl)-4(1H)quinolinone ( 1 ) with acetic anhydride and thionyl chloride gave 3-[[(acetyloxy)methyl]thio]]-1-methyl-4(1H)quinolinone ( 2 ) and 3-[(chloromethyl)thio]-1-methyl-4(1H)quinolinone ( 3 ) respectively. 3-(Methylsulfinyl)-4(1H)cinnolinone ( 4 ) gave the corresponding products when treated under similar conditions. Treatment of 8-methoxy-3-(methylsulfinyl)-4H-1-benzopyran-4-one ( 11 ) with acetic anhydride and thionyl chloride gave bis addition vinyl Pummerer products 2,3-bis(acetyloxy)-2,3-dihydro-8-methoxy-3-(methylthio)-4H-1-benzopyran-4-one ( 12 ) and 2,3-dichloro-2,3-dihydro-8-methoxy-3-(methylthio)-4H-1-benzopyran-4-one ( 13 ), respectively. 相似文献
6.
V. L. Gein N. N. Kasimova Z. G. Aliev M. I. Vakhrin 《Russian Journal of Organic Chemistry》2010,46(6):875-883
The reactions of methyl 2,4-dioxo-4-phenylbutanoate and methyl 2,4-dioxopentanoate with a mixture of an aromatic aldehyde
and propane-1,2-diamine, depending on the initial reactant ratio, gave 4-acyl-1-(2-aminopropyl)-5-aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2-ones and 1,1′-(propane-1,2-diyl)bis(4-acetyl-3-hydroxy-5-phenyl-2,5-dihydro-1H-pyrrol-2-one). Reactions of substituted 1-(2-aminopropyl)-2,5-dihydro-1H-pyrrol-2-ones with aromatic amines and hydrazines were studied, and the structure of one of the products, 5-(2-aminopropyl)-3,4-diphenylpyrrolo[3,4-c]pyrazol-6-one, was proved by X-ray analysis. 相似文献
7.
The reaction of methyl 2-bromo-6-(trifluoromethyl)-3-pyridinecarboxylate ( 1 ) with methanesulfonamide gave methyl 2-[(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridine-carboxylate ( 2 ). Alkylation of compound 2 with methyl iodide followed by cyclization of the resulting methyl 2-[methyl(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridinecarboxylate ( 3 ) yielded 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 4 ). The reaction of compound 4 with α,2,4-trichlorotoluene, methyl bromopropionate, methyl iodide, 3-trifluoromethylphenyl isocyanate, phenyl isocyanate and 2,4-dichloro-5-(2-propynyloxy)phenyl isothiocyanate gave, respectively, 4-[(2,4-dichlorophenyl)methoxy]-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazine 2,2-dioxide ( 5 ), methyl 2-[[1-methyl-2,2-dioxido-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4-yl]oxy]propanoate ( 6 ), 1,3,3-trimethyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 7 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-[3-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 8 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-phenyl-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 9 ) and N-[2,4-dichloro-5-(2-propynyloxy)phenyl]-4-hydroxy-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2] thiazine-3-carboxamide 2,2-dioxide ( 10 ). 相似文献
8.
As a part of metabolic studies of mosapride ( 1 ), a potential gastroprokinetic agent, the synthesis of 4-chloro-7-ethoxy-2(3H)-benzoxazolone-6-carboxylic acid ( 7 ) as a derivative of 4-amino-5-chloro-2-ethoxy-3-hydroxybenzoic acid ( 6 ), which has served a benzoic acid part of the metabolites 4 and 5 , is described. Treatment of methyl 3-amino-4-substituted amino-5-chloro-2-ethoxybenzoate derivatives 11a-c with sodium nitrate in acidic medium gave the benzotriazole derivatives 13x,y instead of the objective 3-hydroxy counterpart. The synthesis of 7 started from o-vanillin acetate ( 15 ) and proceeded through the intermediates 2-hydroxy-3-methoxy-4-nitrobenzaldehyde ( 18 ), methyl 4-amino-2,3-dihydroxybenzoate ( 23 ), and methyl 7-hydroxy-2(3H)-benzoxazolone-6-carboxylate ( 30 ). Compound 30 was alternatively prepared from 23 via methyl 4-ethoxycarbonylamino-2-ethoxycarbonyloxy-3-hydroxybenzoate ( 29 ), which is the product resulting from the migration of the ethoxycarbonyl group of methyl 4-amino-2,3-diethoxycar-bonyloxybenzoate ( 27 ). 相似文献
9.
Zusammenfassung Die Oxidation des Acridonalkaloids Acronycin (1) mit Kaliumpermanganat führt zu (1S-cis)-1,2,3,12-Tetrahydro-1,2-dihydroxy-6-methoxy-3,3,12-trimethyl-7-H-pyrano[2,3-c]acridin-7-on (2), 1-Hydroxy-6-methoxy-3,3,12-trimethyl-1H-pyrano[2,3-c]acridin-2,7(3H,12H)-dion (3) und 1-Hydroxy-6-methoxy-3,3,12-trimethyl-1-(2-oxopropyl)-1H-pyrano[2,3-c]acridin-2,7(3H,12H)-dion (4).
Natural product chemistry, part. 174 [1]: Oxidation of acronycine by potassium permanganate
Summary Oxidation of the acridone alkaloid acronycine (1) by potassium permanganate results in oxidation of the cromenering to give (1S-cis)-1,2,3,12-tetrahydro-1,2-dihydroxy-6-methoxy-3,3,12-trimethyl-7H-pyrano[2,3-c]acridine-7-one (2), 1-hydroxy-6-methoxy-3,3,12-trimethyl-1H-pyrano-[2,3-c]acridine-2,7(3H,12H)-dione (3) and 1-hydroxy-6-methoxy-3,3,12-trimethyl-1-(2-oxopropyl)-1H-pyrano[2,3-c]acridine-2,7(3H,12H)-dione (4).相似文献
10.
Summary The reaction of 3-iodo-4-methoxy-2(1H)-quinolinone (1) and 3-iodo-4,6,8-trimethoxy-2(1H)-quinolinone (2) with 2-methyl-3-butyn-2-ol under modified Heck-conditions gave the 2-substituted derivatives 2-(1-hydroxy-1-methylethyl)-4-methoxyfuro[2,3-b]-quinoline (3) and 2-(1-hydroxy-1-methylethyl-4,6,8-trimethoxyfuro[2,3-b]-quinoline (4). By a subsequent hydrogenation-reaction with a homogeneous catalyst (PtO2/Rh2O3), the furoquinoline-derivatives yielded the dihydrofuro-[2,3-b]quinolines, identified as 2-(1-hydroxy-1-methylethyl-4-methoxy-2,3-dihydrofuro[2,3-b]quinoline (5) (racemic platydesmine) and 2-(1-hydroxy-1-methylethyl)-4,6,8-trimethoxy-2,3-dihydrofuro-[2,3-b]quinoline (6) (racemic precursor of O4-methylptelefolonium salt). 相似文献
11.
Jimmy Orjala Anthony D. Wright Clemens A. J. Erdelmeier Otto Sticher Topul Rali 《Helvetica chimica acta》1993,76(4):1481-1488
Five New unusual monoterpene-substituted dihydrochalcones, the adunctins A–E (1″S)-1-{2′-hydroxy-4′-methoxy-6′-[4″-methyl-1″-(1?-methylethyl)cyclohex-3″ -en-1″ -yloxy]phenyl}-3-phenylpropan-1-one ( 1 ), (5aR*,8R*,9aR*)-3-phenyl-1-[5′,8′,9′,9′a-tetrahydro-3′-hydroxy-1′-methoxy-8′-(1″-methylethyl)-5′-a-methyldibenzo-[b,d]furan-4′-yl]propan-1-one ( 2 ), (2′R*,4″S*)-1-{6′-hydroxy-4′-methoxy-4″-(1?-methylethyl)spiro[benzo[b]-furan-2′(3′H),1″ -cyclohex-2″ -en]-7′-yl}-3-phenylpropan-1-one ( 3 ), (2′R*,4″R*)-1-{6′-hydroxy-4′-methylethyl-4″-(1?-methylethyl)spiro[benzo[b]furan-2′(3′H),1″-cyclohex-2″-en]-7′-yl}-3-phenypropan-1-one ( 4 ), and (5′aR*,6′S*, 9′R*,9′aS*)-1-[5′a,6′,7′,8′,9′a-hexahydro-3′,6′-methoxy-6′-methyl-9′-(1″-methylethyl)dibenzo[b,d]-furan-4′-yl]-3-phenylpropan-1-one ( 5 ) were isolated from the leaves of Piper aduncum (Piperaceae) by preparative liquid chromatography. In addition, (?)-methyllindaretin ( 6 ), trans-phytol, and α-tocopherol ( = vitamin E) were also isolated and identified. The structures were elucidated by spectroscopic methods, including 1D- and 2D-NMR spectroscopy as well as single-crystal X-ray diffraction analysis. The antibacterial and cytotoxic potentials of the isolates were also investigated. 相似文献
12.
Antonio Guerriero Michele D'Ambrosio Vincenzo Cuomo Francesco Pietra 《Helvetica chimica acta》1991,74(7):1445-1450
Acetone extraction of cultures of the marine ascomycete Leptosphaeria oraemaris (LINDER) on cornmeal disk gave the novel polyketide derivative leptosphaerolide ( = (+)-7-[(1E)-l,3-dimethylpent-1-enyl]-10-hydroxy-3-methoxybenzo[1,2-b:5,4-c′]dipyran-2(9H)-one; (4+)-8) besides the o-dihydroquinone 3-[(1E)-1,3-dimethylpent-1-euyl]-8,10-dihydroxy-7-methoxy-8-(2-oxopropyl)-1H-naphtho[2,3-c]pyran-9(8H)-one ( 1 ) as a 10:9 mixture of epimers. retro-Aldol reaction of 1 gave leptosphaerodione ( = (?)-3-[(1E)-1,3-dimethylpent-1-enyl]-10-hydroxy-7-methoxy-1H-naphtho[2,3-c]pyran-8,9(8H)-dione; (?)-6) which was also present in small amounts in the extracts and which gave 1 on reaction with acetone. It is thus likely that 1 is an artefact of the extraction by acetone. Biogenetically (+)-8 might derive from (?)-6 via an unusual oxidation with loss of CO2. 相似文献
13.
Yu. V. Shklyaev T. S Vshivkova A. G. Tolstikov 《Chemistry of Heterocyclic Compounds》2009,45(3):341-344
When treated with cyanoacetic ester in conc. H2SO4 1-(4-hydroxy-3-methoxyphenyl)- and 1-(3-hydroxy-4-methoxyphenyl)-2-methylpropan-1-ol form ethyl 7-hydroxy-6-methoxy-3,3-dimethyl(or
6-hydroxy-7-methoxy- 3,3-dimethyl)-1,2,3,4-tetrahydroisoquinolylidene-1-acetate.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 421-425, March, 2009. 相似文献
14.
Condensation of aromatic (heteroaromatic) aldehydes with 1,3-dicarbonyl compounds under the 1-butyl-3-methylimidazolium tetrafluoroborate
([Bmim][BF4]) ionic liquid-piperidinium acetate catalytic system (0.2 equiv. of each component) in the absence of a solvent affords,
depending on the structures of the reagents, 2-arylidene derivatives of methyl acetoacetate and acetylacetone, diethyl 2,4-bis(trifluoroacetyl)-3-phenylpentanedioate,
or dimethyl 2-aryl-4-hydroxy-6-oxocyclohexane-1,3-dicarboxylates. The reactions of the resulting 2-arylidene derivatives with
O-methylisourea in the [Bmim][BF4] ionic liquid produced methyl 2-methoxy-4-methyl-6-aryldihydropyrimidine-5-carboxylates and 1-(2-methoxy-4-methyl-6-phenyldihydropyrimidin-5-yl)ethanone
(mixtures of 3,6- and 1,6-dihydro isomers), which were transformed into the corresponding 3,4-dihydropyrimidin-2(1H)-one derivatives.
Dedicated to Academician N. K. Kochetkov on the occasion of his 90th birthday.
__________
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 5, pp. 1199–1204, May, 2005. 相似文献
15.
Krivonogov V. P. Kozlova G. G. Sivkova G. A. Spirikhin L. V. Abdrakhmanov I. B. Murinov Yu. I. Tolstikov G. A. 《Russian Journal of Organic Chemistry》2003,39(2):257-260
A reaction was studied of previously unknown 1,3-bis(2-hydroxy-3-chloropropyl)uracil, 1,3-bis(2- hydroxy-3-chloropropyl)-6-methyluracil, and 1,3-bis(2-hydroxy-3-chloropropyl)-5-fluorouracil with 1,3-bis[3-(3-methyl-2H-5-pyrazolon-1-yl)-2-hydroxypropyl]-6-methyluracil. 相似文献
16.
Reactions of methyl acetyl- or benzoylpyruvates with aromatic aldehydes and ethylenediamine, depending on the reactant ratio, afforded 4-acyl-1-(2-aminoethyl)-5-aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2-ones or 1,2-bis(4-acyl-5-aryl-3-hydroxy-2-oxo-2,5-dihydro-1H-pyrrol-1-yl)ethanes. Substituted 1-(2-aminoethyl)-3-hydroxy-2,5-dihydro-1H-pyrrol-2-one hydrochlorides were brought into reactions with p-methoxyaniline and hydrazine.__________Translated from Zhurnal Obshchei Khimii, Vol. 75, No. 2, 2005, pp. 282–287.Original Russian Text Copyright © 2005 by Gein, Kasimova. 相似文献
17.
George C. Wright Thomas J. Schwan Nelson J. Miles 《Journal of heterocyclic chemistry》1974,11(6):849-851
The compound 5,6-dihydro-8-hydroxy-9-methoxy-1H,7H-benzo[ij]quinolizine-1,7-dione ( 4a ) was synthesized from 3-(1,4-dihydro-6,7-dimethoxy-4-oxo-1-quinolyl)propionic acid ( 3a , free base), involving spontaneous demethylation with ring closure. The structural assignment of 4a was based on an analogous, unequivocal synthesis of 5,6-dihydro-9-ethoxy-8-hydroxy-1H,7H-benzo[ij]quinolizine-1,7-dione hydrochloride ( 4b ). 相似文献
18.
A. Bolognese R. Liberatore G. Riente G. Scherillo 《Journal of heterocyclic chemistry》1988,25(4):1247-1250
The oxidation mixture of 3-hydroxykynurenine ( 1 ), treated with aqueous acetic anhydride and, subsequently, with acidic methanol, yields the 1-hydroxy-3-carbomethoxy-5-methoxy-11-(β-aspartoyl-N-acetyl-methyl ester)pyrido[3,2-a]phenoxazine ( 5 ), the 1-hydroxy-11-(β-aspartoyl-N-acetyl-methyl ester)-5.H-pyrido[3,2-a]-phenoxazin-5-one ( 6 ), the 1-methoxy-11-(β-aspartoyl-N-acetyl-methyl ester)-5H-pyrido[3,2-a]phenoxazin-5-one ( 6a ), the l,5-dimethoxy-11-(β-aspartoyl-N-acetyl-methyl ester)pyrido[3,2-a]phenoxazine ( 7 ) and the 1-methyl-1(1′-[11-(β-aspartoyl-methyl esterimino)]ethenyl)ketal-1H,5H-pyrido[3,2-a]phenoxazin-5-one ( 8 ). A probable scheme, for the compound formation, is reported. 相似文献
19.
N. T. Pokhodylo V. S. Matiichuk N. D. Obushak 《Russian Journal of Organic Chemistry》2010,46(6):894-897
Reactions of methyl 3-cyclopropyl-3-oxopropanoate with chloroacetone and ammonia, benzaldehyde and ammonia, and benzoquinone
gave, respectively, methyl 2-cyclopropyl-5-methyl-1H-pyrrole-3-carboxylate, dimethyl 2,6-dicyclopropyl-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylate, and methyl 2-cyclopropyl-5-hydroxy-1-benzofuran-3-carboxylate.
Cyclization of methyl 3-cyclopropyl-3-oxopropanoate with ethyl chloro(arylhydrazono)ethanoates and other halohydrazones led
to the formation of 3-substituted 1-aryl-5-cyclopropyl-1H-pyrazole-4-carboxylic acids, and 5-cyclopropyl-1-(quinolin-5-yl)-1H-1,2,3-triazole-4-carboxylic acid was obtained by reaction of the title compound with 5-azidoquinolines. 相似文献
20.
The reaction of 2-styrylbenzoic acids 2 with N-phenylselenosuccinimide (N-PSS) affords 3-phenyl-iso-coumarin derivatives 3 and 3,4-dihydro-3-phenyl-4-(phenylseleno)isocoumarins 4 via selenolactonization. The reaction of 2-styrylbenzamides 5 and 1-(2-aminophenyl)-3-phenyl-2-peropen-1-one derivatives 11 with N-PSS also resulted in the formation of 1-isoquinolone 6 and 4(1H)-quinolone derivatives 12 , respectively. 相似文献