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1.
Luo-Cheng Zhang Bing-Zhu Yin Zhong-Tian Jin Kimiaki Imafuku 《Journal of heterocyclic chemistry》1988,25(1):285-288
3-Acetamidotropolone ( 1a ) reacted with bromine and fuming nitric acid to afford respectively 3-acetamido-7-bromo- ( 1b ) and -5,7-dibromotropolone ( 1c ) and 3-acetamido-5-nitrotropolone ( 1d ). Azo-coupling reaction of 1a gave 3-acetamido-5-(4-methylphenylazo)tropolone ( 1f ). Bromination of 1d and 1f gave 7-bromo-substituted compounds 1e and 1g , respectively. The compounds 1b-g were hydrolyzed to afford 3-aminotropolones 4b-g , which reacted with triethyl orthoformate to give the corresponding 8H-cyclohept[d]oxazol-8-ones 5b-g . Heating of 3-acetamidotropolones 1a-d with polyphosphoric acid gave 2-methyl-8H-cyclohept[d]oxazol-8-ones 6a-d . 相似文献
2.
The appropriate pyridine-2(1H)-thiones were reacted with an equivalent amount of 5-(chloromethyl)-2-hydroxybenzaldehyde in ethanol in the presence of potassium hydroxide to give the corresponding 2-hydroxybenzaldehyde derivatives in excellent yields. The latter derivatives were taken as key synthons for the preparation of the target hybrids. Therefore, 2-hydroxybenzaldehydes were reacted with benzoylglycine in acetic anhydride in the presence of fused sodium acetate at 100°C for 6 hours to afford a new series of nicotinonitrile-coumarin hybrids. The in vitro acetylcholinesterase inhibitory activities were estimated for the new coumarins. The results were expressed as the inhibition percentage of the tested hybrids at concentration of 25 nM, compared to donepezil as a reference (inhibition percentage of 70.5). Coumarin hybrids linked to 6-(4-nitrophenyl) or 6-(4-chlorophenyl)-4-phenylnicotinonitrile exhibited more effective inhibitory activities than donepezil with inhibition percentages of 94.1 and 72.3, respectively. The new coumarins were tested for their free radical-scavenging capabilities against DPPH. Furthermore, some new coumarins were tested for in vitro cytotoxic activity against each MCF-10A, MCF-7, Caco2, and HEPG2. The new hybrids showed cytotoxicity in micromolar range (IC50 of 3.5-13.9 μM) against all tested cell lines. These results clearly demonstrated that the hybrids being tested are not cytotoxic at the concentration required to inhibit acetylcholinesterase effectively. 相似文献
3.
Sherif M. H. Sanad Mahmoud A. E. Hawass Ahmed A. M. Ahmed Mohamed A. A. Elneairy 《合成通讯》2018,48(14):1847-1856
4-(3-(4-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)-6-phenyl-2-thioxo-1,2-di hydro-pyridine-3-carbonitrile (1) reacted with ethyl chloroacetate (2) in ethanolic sodium acetate solution to yield the corresponding ethyl (3-cyanopyridin-2-ylsulphanyl)acetate derivative 3. Intramolecular cyclization of compound 3 was achieved by its heating in DMF containing potassium carbonate to afford the corresponding ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate derivative 4 which reacted with hydrazine hydrate in refluxing pyridine to yield the starting material 3-aminothieno[2,3-b]pyridine-2-carbohydrazide derivative 7. Compound 7 reacted with different reagents such as triethylorthoformate, formic acid, acetic acid and acetic anhydride to afford the target molecules pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-one derivatives 8–10, 12 and 13 in good to excellent yields. On the other hand, pyridine-2(1H)-thione derivative 1 reacted with hydrazine hydrate in refluxing pyridine to give the other starting material 3-amino-1H-pyrazolo[3,4-b]pyridine derivative 20 which reacted with acetylacetone under reflux to afford the target molecule pyrido[2′,3′:3,4]pyrazolo[1,5-a]-pyrimidine derivative 21 in a good yield. The structures of target molecules were elucidated using elemental analyses and spectral data. 相似文献
4.
Convenient synthesis of variously substituted 2-chloro-5,12-dihydro-5-oxobenzoxazolo[3,2-a]quinolines at the 6-position and N-acylated-3-chlorodibenz[b,e][1,4]oxazepin-11(5H)-ones are reported. The former compounds were obtained in 65–93% yield by simply heating N-acyl-4-chloro-N-(2-hydroxyphenyl)-anthranilic acids in acetic anhydride for 4 hours, and the latter by heating sodium salt of N-acyl-4-chloro-N-(2-hydroxyphenyl)anthranilic acids with acetic anhydride. 相似文献
5.
Zhi-Hong Li Zhong-Tian Jin Bing-Zhu Yin Kimiaki Imafuku 《Journal of heterocyclic chemistry》1987,24(3):779-783
3-Acetyltropolone ( 1 ) reacted with bromine, iodine, and nitric acid to afford respectively 3-acetyl-5,7-di-bromotropolone ( 2 ), 3-acetyl-7-iodotropolone ( 3 ), and 3-acetyl-5-nitro- ( 4 ) and 3-acetyl-5,7-dinitrotropolone ( 5 ). Azo-coupling reactions of 1 gave 3-acetyl-5-arylazotropolones 7a-f. The Schmidt reactions of 2 and 3 gave respectively 5,7-dibromo- ( 9 ) and 7-iodo-2-methyl-8H-cyclohept[d]oxazol-8-one ( 10 ), while 4 gave 3-acetamido-5-nitrotropolone ( 11 ). Compounds 2 and 4 reacted with hydroxylamine to give 3-methyl-8H-cyclohept[d]isoxazol-8-ones 12 and 13. The reactions of 2 , 3 , and 4 with hydrazine gave 3-methyl-1,8-dihydrocycloheptapyrazol-8-ones 15 , 16 , and 17. 相似文献
6.
A. V. Bentya R. I. Vas’kevich A. V. Turov E. B. Rusanov M. V. Vovk V. I. Staninets 《Russian Journal of Organic Chemistry》2011,47(7):1066-1073
6-Allyl(diallyl, prop-2-yn-1-yl)amino-1-R-pyrazolo[3,4-d]pyrimidin-4(5H)-ones reacted with iodine to give angularly fused 8-iodomethyl-7,8-dihydro-1-R-imidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-ones which were treated with sodium acetate to obtain 8-methylidene-1-R-7,8-dihydroimidazo[1,2-a]pyrazolo-[4,3-e]pyrimidin-4(6H)-ones as a result of elimination of hydrogen iodide. 8-Methylidene-1-R-7,8-dihydroimidazo[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-ones were converted into 8-methyl-1-R-imidazo[1,2-a]pyrazolo-[4,3-e]pyrimidin-4(5H)-ones on heating to the melting point. 8-Methylidene-1-phenyl-7,8-dihydroimidazo-[1,2-a]pyrazolo[4,3-e]pyrimidin-4(6H)-one underwent isomerization into linearly fused 6-methyl-1-phenyl-1,8-dihydro-4H-imidazo[1,2-a]pyrazolo[3,4-d]pyrimidin-4-one on heating in sulfuric acid. 相似文献
7.
Reactions of methyl 2-isothiocyanatobenzoate with hydroxylamine and alkoxyamines afforded earlier unknown 3-hydroxy-2-sulfanylquinazolin-4(3H)-one (1a) and 3-alkoxy-2-sulfanylquinazolin-4(3H)-ones (1b,c). Base-catalyzed reactions of compound 1a with alkyl halides were not regioselective, yielding O,S-dialkylation products.
In the presence of acetic acid and sodium acetate, compound 1a was alkylated only at the S atom to give 2-alkylsulfanyl-3-hydroxyquinazolin-4(3H)-ones. Selective O-acylation of compound 1a at position 3 yielded 3-acyloxy-2-sulfanylquinazolin-4(3H)-ones. 相似文献
8.
Mohamed I. Ali Abou El-fotooh G. Hamman Salwa F. Mohamed 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3-4):211-216
Abstract 1,2,3,4-Tetrahydro-l-aryl-3,9-dioxo-2,4-diazafluorenes (2) and 1,2,3,4-tetrahydro-1-aryl-9-oxo-3-thi-oxo-2,4-diazafluorenes (3) were newly synthesized. Compounds 3 reacted with chloroacetic acid, α-bromopropanoic acid, or B-bromopropanoic acid in the presence of fused sodium acetate and acetic anhydride to give 2,3-dihydro-5-aryl-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (4), 2-methyl-2,3-dihydro-5-aryl-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (5) and 2,3-dihydro-6-aryl-6H,7H-thiazino[3,2-b]2,4-diazafluorene-4,7-diones (6), respectively. 2,3-Dihydro-2-arylmethylene-5-aryl-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (7) were prepared by the reaction of compounds (3) with chloroacetic acid and aromatic aldehydes in the presence of fused sodium acetate and acetic anhydride or by the reactions of (4) with aromatic aldehydes in the presence of acetic anhydride. 2-(Arylhydroazono)-5-aryl-2,3-dihydro-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (8) were synthesized by coupling (4) with aryldiazonium salts in the presence of pyridine. 相似文献
9.
Mohamed G. Kassem S. A. Shams El-Dine Farid S. G. Soliman Manal N. S. Saudi 《Monatshefte für Chemie / Chemical Monthly》1990,121(8-9):671-675
Summary Approaches leading to 5,6-dihydro-5,6-diphenyl-2-substituted-pyrrolo[3,4-d][1,2,3]-triazol-4(2H,4H)-ones (10) are described. The first approach consists of cyclodehydrating 3(or 4)-hydroxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (4,7) with boiling acetic anhydride. The second approach involves cyclization of 3(or 4)-acetoxyimino-1,5-diphenyl-4(or 3)-(4-substituted phenylhydrazono)pyrrolidin-2-ones (8,9) with elimination of acetic acid upon treatment with sodium hydroxide.Part of the work has been presented at the 8th International Congress of Heterocyclic Chemistry (August 1981), Graz, Austria 相似文献
10.
Vladimir L. Rusinov Grigori V. Zyryanov Tatjana L. Pilicheva Oleg N. Chupakhin Hans Neunhoeffer 《Journal of heterocyclic chemistry》1997,34(3):1013-1019
3-Aryl-1,2,4-triazin-5(2H)-ones 1a-c react with indoles 2a-c in trifluoroacetic acid/chloroform or in boiling butanol or acetic acid to give 3-aryl-6-(indolyl-3)-1,6-dihydro-1,2,4-triazin-5(2H)-ones 3a-g . Oxidation of the dihydro-1,2,4-triazin-5(2H)-ones 3a-e afforded 6-(indolyl-3)-1,2,4-triazin-5(2H)-ones 4a-e , products of nucleophilic substitution of hydrogen in 1a-c . Refluxing 1b with N-methylpyrrote 5b in butanol for an extended time resulted in the formation of 3-(4-chlorophenyl)-6-(1-meuiylpyrrolyl-2)-1,2,4-triazin-5(2H)-one 4h. The reaction of 1a-c with indoles 2a-c , pyrroles 5a,b , 1,3-dimethyl-2-phenylpyrazol-4-one (8) and aminothiazoles 9a,b in acetic anhydride affords the 1-acetyl-3-aryl-6-hetaryl-1,6-dihydro-1,2,4-triazin-5(2H)-ones 6a-s . Reaction of 1a-c with N-methyl-pyrrole 5b in acetic anhydride gives beside the 1:1 addition products 6h-k also the 2:1 addition products 7a-c . 相似文献
11.
I. V. Dyachenko A. I. Vas’kevich R. I. Vas’kevich M. V. Vovk 《Russian Journal of Organic Chemistry》2014,50(6):858-863
2-Allylsulfanylpyrido[3,4-d]pyrimidin-4(3H)-one reacted with arylsulfanyl chlorides in chloroform to give addition products to the exocyclic double bond, which were converted into linearly fused arylsulfanylthiazinopyridopyrimidines by the action of sodium acetate. The reactions of 2-allyl(cinnamyl, propargyl)sulfanylpyrido[3,4-d]pyrimidin-4(3H)-ones with arylsulfanyl chlorides in the presence of an equimolar amount of lithium perchlorate afforded angularly fused arylsulfanylmethylthiazolo- and -thiazinopyridopyrimidines. 相似文献
12.
Treatment of 4-[(3-hydroxy-2-pyridyl)amino]-2-phenyl-5-pyrimidinecarboxylic acid (X) with acetic anhydride under refluxing conditions afforded 10-hydroxy-2-phenyl-5H-pyrido[1,2-a]-pyrimido[4,5-d]pyrimidin-5-one acetate (IX). The intermediate X was prepared from 4-chloro-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester (V). The reaction of V with the sodium salt of 2-amino-3-hydroxypyridine at room temperature gave 4-(2-amino-3-pyridyloxy)-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester (VI). Treatment of VI with a hot aqueous sodium hydroxide solution and subsequent acidification gave X. Involvement of 4-[(3-hydroxy-2-pyridyl)amino]-2-phenyl-5-pyrimidinecaroboxylic acid ethyl ester (VIII) (Smiles rearrangement product) as an intermediate in the above alkaline hydrolysis reaction of VI to X was demonstrated by the isolation of VIII and its subsequent conversion into X under alkaline hydrolysis conditions. Acetylation of VIII with acetic anhydride in pyridine solution gave 4-[(3-hydroxy-2-pyridyl)amino]-2-phenyl-5-pyrimidinecarboxylic acid ethyl ester acetate (XI), which afforded IX on fusion at 220°. This alternative synthesis of IX from XI supported the structural assignment of IX. Fusion of VI gave 10-hydroxy-2-phenyl-5H-pyrido[1,2-a]pyrimido]4,5-d]pyrimidin-5-one (VII). The latter was also obtained when VIII was fused at 210°. Acetylation of VII with acetic anhydride afforded IX. 相似文献
13.
R. I. Vas’kevich P. V. Savitskii E. B. Rusanov V. I. Staninets 《Russian Journal of Organic Chemistry》2010,46(11):1682-1686
1-(6-Methyl-5-oxo-2,5-dihydro-1,2,4-triazin-3-yl)-4-arylthiosemicarbazides treated with methyl iodide in the presence of sodium
acetate in ethanol convert into 6-methyl-3-arylamino[1,2,4]-triazolo[4,3-b][1,2,4]triazin-7(1H)-ones. In reaction with dicyclohexylcarbodiimide 6-methyl-3-arylamino[1,2,4]triazolo[3,4-c][1,2,4]triazin-5(1H)-ones were obtained which at heating in alcohol solution in the presence of sodium acetate or at 262–272°C underwent the
Dimroth rearrangement to give 3-methyl-7-arylamino[1,2,4]triazolo[5,1-c][1,2,4]-triazin-4(8H)-ones. 相似文献
14.
P. Paradesi Naidu Akula Raghunadh K. Raghavendra Rao Ramamohan Mekala J. Moses Babu B. R. Rao 《合成通讯》2014,44(10):1475-1482
Urea/thiourea have been identified as an effective ammonia surrogate in the construction of quinazolin-4(3H)-one ring. This strategy afforded a simple and catalyst-free synthesis of 2-substituted 2,3-dihydroquinazolin-4(1H)-ones and quinazolin-4(3H)-ones via the reaction of isatoic anhydride and aryl aldehydes in the presence of urea or thiourea in ethanol. The reaction proceeded well to afford the quinazolin-4(3H)-one or its dihydro derivative, depending on the nature of carbonyl compounds employed. 相似文献
15.
Kamal A. Kandeel Ali M. Youssef Hany M. El-Bestawy Mohamed T. Omar 《Monatshefte für Chemie / Chemical Monthly》2002,45(8):1211-1219
N,N-Disubstituted 5-arylmethylidene-2-aminothiazol-4(5H)-ones reacted with diethyl malonate, ethyl benzoylacetate, acetylacetone, or cyclopentadiene in refluxing toluene and in presence of powdered sodium to give the respective 5-arylmethylidene-2′-amino-2,5′-bithiazolylidene-4,4′-dione derivatives in moderate yields. 5-Benzylidene-2-morpholin-4-yl-2-thiazol-4(5H)-one reacted with malononitrile in toluene and in presence of powdered sodium under mild conditions to afford the 1:1 adduct, benzylmalononitrile, and 2-morpholin-4-yl-2-thiazol-4(5H)-one. However, similar treatment of 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-one with malononitrile yielded the 2,5′-bithiazolylidene-4,4′-dione derivative together with 4-methoxyphenylmethylidene malononitrile. Treatment of 5-benzylidene- and 5-(4-methoxyphenylmethylidene)-2-morpholin-4-yl-2-thiazol-4(5H)-ones with 3-phenyl-4-oxo-2-thioxo-1,3-thiazolidine in refluxing toluene and in presence of powdered sodium produced 5-arylmethylidene-3-phenyl-4-oxo-2-thioxo-1,3-thiazolidines in good yields. The structures of all products were deduced from microanalytical and spectroscopic data, mechanistic details are discussed. 相似文献
16.
Bakr F. Abdel-Wahab Salwa F. Mohamed Abd El-Galil E. Amr Mohamed M. Abdalla 《Monatshefte für Chemie / Chemical Monthly》2008,31(3):1083-1090
Methyl 2-(thiazol-2-ylcarbamoyl)acetate was synthesized and used as starting material. It was treated with hydrazine hydrate
to afford the hydrazide, which was reacted with nitromethane and formaldehyde to give the saturated nitropyrimidine. The hydrazide
was reacted with phenyl isothiocyanate to afford the thiosemicarbazide, which was cyclized with ethyl bromoacetate, sodium
hydroxide, or sulfuric acid to afford N-phenylthiazolidinone, N-phenyltriazole, and thiadiazolyl derivatives. The methyl 2-(thiazol-2-ylcarbamoyl)acetate was coupled with diazonium salts
of aniline, 4-chloroaniline, 4-bromoaniline, or 4-aminobenzenesulfonamide to afford the carbamoyl acetates, which were reacted
with 2-aminobenzimidazole, 1,2,4,5-tetrachlorophthalic anhydride, and hydrazine hydrate to afford the corresponding thiazolylmalonamide,
tetrachloroisoindolylimide, and tri-azole derivatives. Schiff bases and imides are newly synthesized candidates obtained via simple condensation of the hydrazide with aldehydes, 2,3-pyridinedicarboxylic anhydride, or 1,8-naphthalenedicarboxylic anhydride.
The pharmacological screening showed that many of these compounds have good antihypertensive α-blocking activity and low toxicity. 相似文献
17.
Tetsuo Yamasaki Yuji Yoshihara Yoshinari Okamoto Tadashi Okawara Mitsuru Furukawa 《Journal of heterocyclic chemistry》1992,29(5):1313-1316
The reaction of 5-hydrazinopyridazin-3(2H)-ones 1 with α-keto diester 2 in acetic acid afforded the corresponding 4,6-dihydropyridazino[4,5-c]pyridazin-5(1H)-ones 3 and pyrrolo[2,3-d)pyridazin-4(5H)-ones 4 . Compounds 3 were also obtained from 4-bromo-5-hydrazinopyridazin-3(2H)-ones 8 and 2 under milder conditions. 5-Bromo-4-hydrazinopyridazin-3(2H)-one 9 , the regioisomer of 8b , also reacted readily with 2a to give 4,7-dihydropyridazino[4,5-c]pyridazin-8(1H)-one 10b , the regioisomer of 3b . 相似文献
18.
The reductive coupling of 1,3-dimethyhydantoin with benzophenones by TiCl4-Zn in THF gave 4-diarylmethyl-1H-imidazol-2(3H)-ones as four-electron reduced one-to-one coupled products and their dimers as two-to-two coupled products predominantly by controlling the reaction conditions. The reductive coupling of 5-alkyl-1,3-dimethyhydantoins with benzophenones produced 5-alkyl-4-diarylmethyl-1H-imidazol-2(3H)-ones as the sole products irrespective to the reaction conditions. On the other hand, the reductive coupling of 1,3-dimethyhydantoin with cyclic benzophenones selectively 4-arylhydroxymethyl-1H-imidazol-2(3H)-ones as two-electron reduced one-to-one coupled products and they were further reduced to 4-diarylmethyl-1H-imidazol-2(3H)-ones. 相似文献
19.
Abd El-Galil E. Amr Nermien M. Sabry Mohamed M. Abdulla 《Monatshefte für Chemie / Chemical Monthly》2007,138(7):699-707
Summary. A series of pyridines, pyrimidinones, and oxazinones were synthesized as anti-inflammatory agents using citrazinic acid (2,6-dihydroxyisonicotinic
acid) as a starting material. Acryloyl pyridine was treated with cyanothioacetamide to give cyano pyridine-thione, which was
reacted with ethyl chloroacetate to yield the corresponding amino ester. The ester was hydrolysed to the sodium salt, which
was treated with acetic anhydride to afford 2-methyloxazinone, which was treated with ammonium acetate to afford 2-methylpyrimidinone
followed by methylation with methyl iodide to yield 2,3-dimethylpyrimidinone. In addition, the oxazinone derivative was reacted
with aniline or hydrazine hydrate to give 3-phenyl- or 3-aminopyrimidinones. The latter reacted with thiophene-2-carboxaldehyde
or phenylisothiocyanate to afford Schiff’s bases or thiosemicarbazides. 3-Aminopyrimidinone was treated with phthalic anhydride or 1,2,4,5-benzenetetracarboxylic
acid dianhydride or toluene-3,5-diisocyanate to afford the corresponding imide, bis-imide, and bis-semicarbazide derivatives. The pharmacological screening showed that many of these compounds have good anti-inflammatory
activity comparable to Prednisolone? as reference drug. 相似文献
20.
Marzoog S. Al-Thebeiti 《Journal of carbohydrate chemistry》2013,32(6):667-674
ABSTRACT Cyclic ketones 1a-f reacted with mercaptoacetic acid in benzene and/or toluene in the presence of p-toluenesulfonic acid afforded the corresponding spiro-1,3-oxathialanone derivatives (2a-f). Compounds 2a-f reacted with glucosamine hydrochloride in a mixture of pyridine and ethanol to yield 3-(2′-glucosyl)-2-spiro[1′-cycloalkyl]thiazolidin-4-one derivatives 4a-f. Reaction of 4a-f with fused sodium acetate in a mixture of acetic anhydride and acetic acid gave annulated spirothiazoloxazologlucose derivatives 6a-f. All the synthesized spiro derivatives were identified by conventional methods (IR, 1H NMR spectroscopy and elemental analyses). 相似文献