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1.
Condensation of cinchomeronic acid with p-nitrophenylacetic acid, of 2, 6-dimethylcinchomeronic acid with phenylacetic acid, and p-nitrophenylacetic acid in acetic anhydride solution in the presence of triethylamine followed by rearrangement of the condensation products with sodium methoxide gives 2-(p-nitrophenyl)-5-azaindandione-1, 3, 4, 6-dimethyl-2-phenyl-5-azaindandione-1, 3, and 4, 6-dimethyl-2-(p-nitrophenyl)-5-azaindandione-1, 3. Reaction of the alkali metal salts of these compounds with dimethyl sulfate leads to alkylation at the nitrogen atom, and formation of N-methyl betaines of the corresponding 5-azaindandiones. 2-Aryl-5-azaindandiones and their N-methyl betaines are dark in color (black to reddish brown), sparingly soluble, and decompose at 250-350°.  相似文献   

2.
3,4-Diaryl-5-[4-(acetylsulfamoyl)phenyl]-4,5-dihydropyrrolo[3,4-c]pyrazol-6(2H)-ones were synthesized be reaction of 5-aryl-4-aroyl-1-[4-(acetylsulfamoyl)phenyl]-3-hydroxy-1H-pyrrole-2(5H)-ones with hydrazine hydrate in glacial acetic acid, and their sodium salts were obtained by treatment with sodium methoxide in methanol–DMF (1: 1). Analgesic and anti-inflammatory activity and acute toxicity of the synthesized compounds were studied.  相似文献   

3.
6-Allylsulfanyl-1-arylpyrazolo[3,4-d]pyrimidin-4(5H)-ones react with iodine and sulfuric acid to give angular pyrazolothiazolopyrimidine derivatives. The reaction of 6-(prop-2-yn-1-ylsulfanyl)-1-(4-tolyl)-pyrazolo[3,4-d]pyrimidin-4(5H)-one with sulfuric acid gives angularly fused pyrazolo[4,3-e][1,3]thiazolo-[3,2-a]pyrimidin-4-one, whereas in the reaction with sodium methoxide linearly fused pyrazolo[3,4-d][1,3]-thiazolo[3,2-a]pyrimidin-4-one was formed. Linearly fused pyrazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazole derivatives were also obtained by reaction of 1-aryl-6-(3-phenylprop-2-en-1-ylsulfanyl)pyrazolo[3,4-d]pyrimidin-4(5H)-ones with sulfuric acid.  相似文献   

4.
Condensation of 2-hydroxymethylnicotinic and 2-hydroxymethylquinoline-3-carboxylic acid lactones with aromatic aldehydes in the presence of sodium methoxide gives, respectively, 2-aryl-4-azaindan-1,3-diones and 2-aryl-4-aza-5,6-benzindan-1,3-diones. Alkylation of 2-aryl-4-azaindan-1,3-diones with diazomethane gives the N-methylbetaines. According to the IR spectra, in the solid state the 4-azaindan-1,3-diones seemto have a strongly polarized enol structure.Translated from Khimiya Geterotsiklicheskikh Soedinenii, Vol. 6, No. 5, pp. 647–650, May, 1970.  相似文献   

5.
Ethyl 2-amino-5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carboxylates and 2-amino- 5-(2-aryl-2-oxoethylidene)-4-oxo-1H-4,5-dihydrofuran-3-carbonitriles reacted with alcohols in the presence of a catalytic amount of concentrated aqueous HCl to give the corresponding 5-alkoxy-2-amino-5-(2-aryl-2- oxoethyl)-4-oxo-1H-4,5-dihydrofuran-3-carboxylic acid derivatives. A probable reaction mechanism was proposed on the basis B3LYP/6-311G(d) quantum chemical calculations.  相似文献   

6.
Cyclopropanation of methyl (2E)-3-[(1R,6S)-7,7-dimethyl-2-oxo-3-oxabicyclo[4.1.0]hept-4-en-4-yl]prop-2-enoate with dichlorocarbene occurred at the endocyclic double bond, while its reaction with diazomethane in the presence of Pd(acac)2 involved the exocyclic double bond. The resulting lactones reacted with sodium methoxide in methanol via opening of one cyclopropane fragment.  相似文献   

7.
Alkylation of sodium 4(5)-alkyl-6-oxo-1,6-dihydropyrimidine-2-thiolates with 2-bromo-1-(4-bromophenyl)ethan-1-one afforded 2-{[2-(4-bromophenyl)-2-oxoethyl]sulfanyl}pyrimidin-4(3H)-ones. Analogous reaction with sodium 4-trifluoromethyl-6-oxo-1,6-dihydropyrimidine-2-thiolate gave a mixture of 2-{[2-(4-bromophenyl)-2-oxoethyl]sulfanyl}-4-(trifluoromethyl)pyrimidin-4(3H)-one and its intramolecular cyclization product, 3-(4-bromophenyl)-3-hydroxy-7-trifluoromethyl-2,3-dihydro[1,3]thiazolo[3,2-a]-pyrimidin-5-one.  相似文献   

8.
2-[2-(4-Chlorophenyl)-2-oxoethylidene]-5-phenylfuran-3(2H)-one and methyl (5-aryl-3-oxo-2,3-dihydrofuran-2-ylidene)acetates react with carboxylic acid hydrazides to give the corresponding 3-substituted 2-acyl-6-aryl-3-hydroxy-2,3-dihydropyridazin-4(1H)-ones. Specificities of the product structure are discussed.  相似文献   

9.
Condensation of acetylferrocene with 5-phenyl(4-methylphenyl)-1,2-oxazole-3-carbaldehydes afforded (Е)-3-[5-phenyl(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-ones. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with semicarbazide, thiosemicarbazide, and hydroxylamine led to the formation of 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole- 1-carboxamide, 5-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-3-ferrocenyl-4,5-dihydro-1H-pyrazole-1-carbothioamide, and 5-(4-methylphenyl)-3'-ferrocenyl-4',5'-dihydro-3,5'-bi-1,2-oxazole respectively. Reactions of (Е)-3-[5-(4-methylphenyl)-1,2-oxazol-3-yl]-1-ferrocenylprop-2-en-1-one with guanidine and thiourea result in 4-[5-(4-methyl-phenyl)-1,2-oxazol-3-yl]-6-ferrocenylpyrimidin-2-amine and -2-thione respectively.  相似文献   

10.
Hydrochloric acid reacts with 5-ethyl-2-methallylsulfanyl-6-methylpyrimidin-4(3H)-ones to protonate the nitrogen atom; it adds to the double bond of 2-prenylsulfanyl-6-(trifluoromethyl)pyrimidin-4(3H)-one and gives the addition and heterocyclization products in the case of 2-prenylsulfanyl-6-methylpyrimidin-4(3H)-one.  相似文献   

11.
2,3-Alkadienoates as Dienophiles, Application in the Synthesis of (+)-(R)-Lasiodiplodin Methyl 2, 3-alkadienoates 2 are shown to react at 80° with l, 1-dimethoxy-3trimethylsilyloxy-l, 3-butadiene (1) to give the adducts 3 in good yields. Rearrangement of 3 , catalyzed by p-toluenesulfonic acid or by sodium methoxide, affords the 6-substituted methyl 4-hydroxy-2-methoxybenzoates 4 (R ? H, CH3, C6H5). An analogous reaction sequence starting with (-)-(11 R)-dodeca-2, 3-dien-11-olide ((-) -6 ) and 1 leads, via the adduct (R)-7 , to (+)-( R )-lasiodiplodin ((+) ?8 ) with properties identical to those of the natural product. The allene lactone (-) -6 was prepared by an intramolecular Wittig condensation of (R) ?5 , produced from (–)-(R)-9-hydroxydecanoic acid.  相似文献   

12.
Diazotization of 2-amino-1,3,4-thiadiazoles gave 1,3,4-thiadiazole-2-diazonium sulfates which were converted to 2-azido-1,3,4-thiadiazoles. The latter reacted with ethyl acetoacetate in the presence of sodium methoxide in methanol to produce 1-(5-R1-1,3,4-thiadiazol-2-yl)-5-R2-1H-1,2,3-triazole-4-carboxylic acid derivatives. The reactions of 2-azido-5-methyl-1,3,4-thiadiazole and 2-azido-1,3-thiazole with ethyl 3-(1,3-benzodioxol-5-yl)-3-oxopropanoate led to the formation of 1,2,3-triazole ring under milder conditions (K2CO3, DMSO). Various 1,2,3-triazole-4-carboxylic acid derivatives were synthesized.  相似文献   

13.
Preparative method for the synthesis of lithium, sodium, cesium, and calcium salts of (E)-4-(5-arylisoxazol-3-yl)methyleneaminobutanoic, (E)-6-(5-arylisoxazol-3-yl)methyleneaminohexanoic, (E,S)-3-methyl-2-(5-arylisoxazol-3-yl)methyleneaminobutanoic, (E,S)-4-methyl-2-(5-arylisoxazol-3-yl)methyleneaminopentanoic and (E,2S,3S)-3-methyl-2-(5-arylisoxazol-3-yl)methyleneaminopentanoic acids was developed by reacting 5-phenyl(4-tolyl)isoxazole-3-carbaldehydes with amino acids like 4-aminobutyric and 6-aminocaproic acids, L-valine, L-leucine or L-isoleucine in the presence of lithium hydride, sodium methoxide, cesium carbonate or calcium hydride in boiling methanol.  相似文献   

14.
Condensation of 1,1-diamino-2,2-dinitroethylene with glyoxal and formaldehyde in water solutions at pH 7–8 gave rise to 2-(dinitromethylene)imidazolidine-4,5-diol and 1,1-diamino-N,N′-bis(hydroxymethyl)-2,2-dinitroethylene respectively. Condensation products of 2-(dinitromethylene)imidazolidine-4,5-diol with acetonitrile, benzonitrile, urethane, 3,4-diaminofurazan were isolated. The reaction of 4,5-diacetamido-2-(dinitromethylene) imidazolidine sulfate with water in acetonitrile led to the formation of 2-(dinitromethylene)-5-methyl-1,2,3,3a,4,6a-hexahydroimidazo[4,5-d]imidazole. The dehydration of 2-(dinitromethylene)imidazolidine-4,5-diol in a system H2SO4-AcOH provided 2-(dinitromethylene)-2,3-dihydro-1H-imidazol-4-ol. 1,1-Diamino-N,N′-bis(hydroxymethyl)-2,2-dinitroethylene in sulfuric acid was converted into 4-(dinitromethylene)-1,3,5-oxadiazinane.  相似文献   

15.
Condensation of 3-(4-fluorophenyl)-1H-pyrazole-4-carbaldehyde with 2-naphthyl-or 6-quinolylamine and CH-acids (acetone, acetophenone, cyclic mono-and β-diketones) provided new derivatives of benzo[f]quinoline, benzo[a]phenanthridine, benzo[a]acridine, and 4,7-phenanthroline. The arising in the course of the reaction [3-(4-fluorophenyl)-1H-pyrazole-4-ylmethylene]-2-naphthyl-(or 6-quinolyl)amines, [3-(4-fluorophenyl)-1H-pyrazole-4-ylmethylene]-1,3-indandione, and octahydro-1,8-xanthenedione derivatives were isolated.  相似文献   

16.
Reaction of ethyl or methyl 2-dimethylaminomethylene-3-oxoalkanoates with hydroxylamine hydrochloride in methanol solution afforded in high yields the relative esters of 5-substituted 4-isoxazolecarboxylic acids II . These esters were hydrolyzed generally with concentrated hydrochloric acid-acetic acid mixtures to the corresponding carboxylic acids in satisfactory yields. Ethyl or methyl esters II isomerized with sodium ethoxide or methoxide, respectively, to the corresponding esters or hemiesters of 2-cyano-3-oxoalkanoic acids generally in excellent to satisfactory yields. Reaction of methyl 5,5-dimethyl-3-dimethylaminomethylene-2,4-dioxohexanoate with hydroxylamine hydrochloride afforded in moderate yield methyl 4-(2,2-dimethyl-1-oxopropyl)-5-isoxazolecarboxylate, which was converted by acid hydrolysis as above to 4-t-butyl-4-hydroxyfuro[3,4-d]isoxazol-6-(4H)-one.  相似文献   

17.
A new C-glycosyl precursor for C-nucleoside synthesis, 2,5-anhydroallonamidine hydrochloride ( 4 ) was prepared and utilized in a Traube type synthesis to prepare 2-(β-D-ribofuranosyl)pyrimidines, a new class of C-nucleosides. The anomeric configuration of 4 was confirmed by single-crystal X-ray analysis. Reaction of 4 with ethyl acetoacetate gave 6-methyl-2-(β-D-ribofuranosyl)pyrimidin-4-(1H)-one ( 5 ). Reaction of 4 with diethyl sodio oxaloacetate gave 2-(β-D-ribofuranosyl)pyrimidin-6(1H)-oxo-4-carboxylic acid ( 6 ). Esterification of 6 with ethanolic hydrogen-chloride gave the corresponding ester 7 which when treated with ethanolic ammonia gave 2-(β-D-ribofuranosyl)pyrimidin-6(1H)-oxo-4-carboxamide ( 8 ). Condensation of 2,5-anhydroallonamidine hydrochloride ( 4 ) with ethyl 4-(dimethylamino)-2-oxo-3-butenoate ( 9 ), gave ethyl 2-(β-D-ribofuranosyl)pyrimidine-4-carboxylate ( 10 ). Treatment of 10 with ethanolic ammonia gave 2-(β-D-ribofuranosyl)pyrimidine-4-carboxamide ( 11 ). Single-crystal X-ray analysis confirmed the β-anomeric configuration of 11. Acetylation of 11 followed by treatment with phosphorus pentasulfide and subsequent deprotection with sodium methoxide gave 2-(β-D-ribofuranosyl)pyrimidine-4-thiocarboxamide ( 14 ). Dehydration of the acetylated amide 12 with phosphorous oxychloride provided 2-(β-D-ribofuranosyl)pyrimidine-4-carbonitrile ( 15 ). Treatment of 15 with sodium ethoxide gave ethyl 2-(β-D-ribofuranosyl)pyrimidine-4-carboximidate ( 16 ), which was converted to 2-(β-D-ribofuranosyl)pyrimidine-4-carboxamidine hydrochloride ( 17 ) by treatment with ethanolic ammonia and ammonium chloride. Treatment of 16 with hydroxylamine yielded 2-(β-D-ribofuranosyl)pyrimidine-4-N-hydroxycarboxamidine ( 18 ). Treatment of 2-(β-D-ribofuranosyl)pyrimidine-4-carboxamide ( 11 ) with phosphorus oxychloride gave the corresponding 5′-phosphate, 19 , Coupling of 19 with AMP using the carbonyldiimidazole activation procedure gave the corresponding NAD analog, 2-(β-D-ribofuranosyl)pyrimidine-4-carboxamide-(5′ ? 5′)-adenosine pyrophosphate ( 20 ).  相似文献   

18.
The syntheses of 3-hydroxy-4-hydroxymethyl-2-methyl-5-pyridineacetic and -5-pyridine-propionic acids and several related compounds are described. Although acid hydrolysis of α4,3-O-isopropylidene-5-pyridoxic acid gives 5-pyridoxic acid lactone (α-pyracin), its higher homolog α4,3-O-isopropylidene-pyridoxylformic acid gave a corresponding free alcohol whose carboxylic acid proton was shown to be exchanged rapidly with the 3-phenolic and -4-alcoholic - protons in nuclear magnetic resonance studies. Inter-molecular hydrogen bonding between the side chain carboxylic acid and pyridine nitrogen atoms is suggested in the solid state.  相似文献   

19.
Condensation of ephedrine alkaloids with 5-bromo-2-hydroxybenzaldehyde was studied, and X-ray diffraction analysis of the synthesized (2S,4S,5R)-2-(2-hydroxy-5-bromophenyl)-3,4-dimethyl-5-phenyl-1,3-oxazolidines was performed.  相似文献   

20.
Synthetic methodology that allows for incorporation of isotopic carbon at the C-3 and C-4 positions of bile salts is reported. Three [3,4-(13)C(2)]-enriched bile salts were synthesized from either deoxycholic or lithocholic acid. The steroid 3alpha-OH group was oxidized and the A-ring was converted into the Delta(4)-3-ketone. The C-24 carboxylic acid was next converted into the carbonate group and selectively reduced to the alcohol in the presence of the A-ring enone. Following protection of the 24-OH group, the Delta(4)-3-ketone was converted into the A-ring enol lactone. Condensation of the enol lactone with [1,2-(13)C(2)]-enriched acetyl chloride and subsequent Robinson annulation afforded a [3,4-(13)C(2)]-enriched Delta(4)-3-ketone that was subsequently converted back into a 3alpha-hydroxy-5beta-reduced bile steroid. C-7 hydroxylation, when necessary, was achieved via conversion of the Delta(4)-3-ketone into the corresponding Delta(4,6)-dien-3-one, epoxidation of the Delta(6)-double bond, and hydrogenolysis/hydrogenation of the 5,6-epoxy enone system. The [3,4-(13)C(2)]-enriched bile salts were subsequently complexed to human ileal bile acid binding protein (I-BABP), and (1)H-(13)C HSQC spectra were recorded to show the utility of the compounds for investigating the interactions of bile acids with I-BABP.  相似文献   

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