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1.
This paper reports the synthesis of new pyrido[2,3- d]pyrimidin-4-one derivatives as diuretic agents. Starting with 1,2-dihydro-5-nitro-2-oxo-3-pyridinecarboxylic acid 1 , ethyl 2-ethoxy-5-nitro-3-pyridincarboxylate 4 was obtained. Compound 4 reacts with ammonia, methylamine or S-methylpseudothiourea to give the respective 2-amino-5-nitro-3-pyridinecarboxamide derivatives 5 and 6 or 2-methylthio-6-nitro-3 H-pyrido[2,3- d]pyrimidin-4-one 8. Treating carboxamide 5 with arylaldehydes and zinc dichloride, new 2-aryl-1,2-dihydro-6-nitro-3 H-pyrido[2,3- d]pyrimidin-4-ones 9 were synthetised. These compounds reduced with iron(II) hydroxide gave 6-amino-2-aryl-1,2-dihydro-3 H-pyrido[2,3- d]pyrimidin-4-ones 10 as expected. 相似文献
2.
Monoacylketene aminals containing an unsubstituted NH 2 group react as C-nucleophiles with benzoyl isothiocyanate to give the corresponding thioamides which undergo cyclization by sodium methoxide in methanol to afford 6-R-amino-5-acetyl-2-phenyl-3 H-pyrimidine-4-thiones. A scheme for constructing the pyrido[2,3- d]pyrimidine system from keteneaminals is offered. The reaction of 6-R-amino-5-acetyl-2-phenyl-3 H-pyrimidine-4-thiones with dimethylformamide dimethylacetal leads to 8-R-N-4-methylthio-8 H-pyrido-[2,3- d]pyrimidine-5-ones. Cyclization of 5-acetyl-6-benzoylamino-4-methylthio-2-phenylpyrimidine by sodium methoxide yields N-unsubstituted 4-methylthio-8 H-pyrido-[2,3- d]pyrimidine-5-one.Translated from Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 1932–1937, November, 1993 相似文献
3.
Summary Several 7-methyl-5-alkyl-2-vinylpyrazolo[3,4- d]pyrimidine-4,6(5 H,7 H)-diones were prepared. The successful cyclization and alkylation of 6-(-methylbenzylidenehydrazino)-1-methyluracils 2a–d using dimethylformamide acetals at high temperature provided 6a–d, 7a–d, and 8a–d. Treatment of 6a–d and 7a–d with acid afforded 7-methyl-5-alkylpyrazolo[3,4- d]pyrimidine-4,6(5 H,7 H)-diones 9a, b; under the same conditions, 3a–d reacted to 7-methylpyrazolo[3,4- d]-pyrimidine-4,6(5 H)-dione ( 4) in good yield.
DMF-Acetale als Alkylierungs- und Ringschlußreagentien: ein einfacher Weg zu substituierten Pyrazolo[3,4-d]pyrimidin-4,6(5H,7H)-dionen Zusammenfassung Es wurden verschiedene 7-Methyl-5-alkyl-2-vinylpyrazolo[3,4-d]pyrimidin-4,6(5H,7H)-dione hergestellt. Cyclisierung und Alkylierung der 6-(-Methylbenzylidenhydrazino)-1-methyl-uracile2a–d mit Hilfe von Dimethylformamidacetalen bei hohen Temperaturen ergab6a–d,7a–d und8a–d. Behandlung von6a–d und7a–d mit Säure lieferte die 7-Methyl-5-alkylpyrazolo[3,4-d]pyrimidin-4,6(5H,7H)-dione9a,b; unter den gleichen Bedingungen reagierten3a–d in guter Ausbeute zu 7-Methylpyrazolo[3,4-d]pyrimidin-4,6(5H)-dion (4). 相似文献
4.
Some new 7,9-disubstituted 7 H-1,2,3,4-tetrazolo[1,5- c]pyrrolo[3,2- e]pyrimidines 5 have been synthesized either by diazotization of 4-hydrazino-5,7-disubstituted-7 H-pyrrolo[2,3- d]pyrimidines 4 obtained by hydrazinolysis of 4-chloro-5,7-disubstituted-7 H-pyrrolo[2,3- d]pyrimidines 3 or via a substitution reaction between 3 and sodium azide. 5,7-Disubstituted-7 H-pyrrolo[2,3- d]pyrimidin-4(3 H)-ones 2 were obtained by cyclocondensation of 2-amino-3-cyano-1,4-disubstituted pyrroles 1 with formic acid which on chlorination using phosphorus oxychloride afforded 3 . A novel route for the synthesis of 4-amino-5,7-disubstituted-7 H-pyrrolo[2,3- d]pyrimidines 6 by the reductive ring cleavage of 5 has been reported. 相似文献
5.
2-R-5-Imino-6 H-1,3,4-thiadiazolo[3,2- a]pyrimidin-7-ones react with aromatic and heterocyclic aldehydes in the presence of Et 3N to give condensation products on the methylene group, which react with carbon disulfide to yield the corresponding 2,6-disubstituted
8-thioxo-9,9a-dihydro-1,3,4-thiadiazolo[3′,2′∶1,2]pyrimidino[5,6- d]1,3-thiazin-5-ones.
Deceased.
Translated from Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 366–368, February, 1999. 相似文献
6.
5 H-Pyrido[1,2- a]pyrimido[5,4- e]pyrimidin-5-ones IVa,b and 5 H-pyrido[1,2- a]pyrimido[4,5- d]pyrimidin-5-ones Va,b were synthesized from ethyl 4-chloro-5-pyrimidinecarboxylate and 2-aminopyridine. The former compounds were obtained directly upon heating the reactants in ethanol, and the latter were prepared by the fusion of ethyl 4-(2-pyridylamino)-5-pyrimidinecarboxylates obtained as minor products from the above reaction. The angular fused cyclic compounds, IVa,b were rearranged to the linear tricycles, Vb-f upon heating with amines. 相似文献
7.
N-(1-Chloro-2,2,2-trihaloethylidene)-O-methylurethanes undergo cyclization with 5-amino-3-methylisoxazole and 3-amino-5-methylisoxazole to give respectively 6-trihalomethylisoxazolo[5,4- d]pyrimidin-4(5H)-ones and 2-trihalomethyl-4H-isoxazolo[2,3- a]-1,3,5-triazin-4-ones. 相似文献
8.
Isothiocyanate 2, obtained from aza-Wittig reaction of iminophosphorane 1 with CS 2, reacted with amine to give 2-thioxo-2,3,5,6,7,8-hexahydrobenzothieno[2,3- d]pyrimidin-4(1 H)-ones 4 in the presence of sodium ethoxide. S-Alkylation of 4 produced 2-alkylthio-5,6,7,8-tetrahydrobenzothieno[2,3- d]pyrimidin-4(3 H)-ones 5 in good yields. 相似文献
9.
Abstract The reaction of 2-mercapto-6,7,8,9-tetrahydro-3 H-benzo[4,5]thieno[2,3- d]pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3- d]-1,2,4-triazolo[4,5- a]pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3 H-benzo[4,5]thieno[2,3- d]pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride
to afford the non-isolable azo-coupling products which converted, in situ, to 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3- d]-1,2,4-triazolo[4,5- a]pyrimidin-5-ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some
of the newly synthesized compounds had a moderate effect against some bacterial and fungal species. 相似文献
10.
By condensing alicyclic β-ketocarboxylates with substituted 2-aminopyridines in polyphosphoric acid or phosphoryl chloride-polyphosphoric acid, numerous 2,3-tri-, tetra-, penta- and hexamethylene-4 H-pvrido[1,2- a]pyrimidin-4-ones were synthesized for pharmacological purposes. The stability and several reactions of the title compounds were studied. The 6-substituted-4 H-pyrido[1,2- a]pyrimidin-4-ones were transformed into 1,8-naphthyridines in good yields independent of the ring size of ring C . The characteristic differences in the ir and uv spectra of the pyrido-pyrimidines and the corresponding naphthyridines are discussed. Catalytic hydrogenation of the pyrido[1,2- a]pyrimidin-4-ones furnished the corresponding 6,7,8,9-tetrahydropyrido-[1,2- a]pyrimidin-4-one derivatives. It was found that the A and C rings attached to the pyrirnidinone ring in solutions of unsubstituted tetrahydropyrido[1,2- a]pyrimidin-4-ones are flexible, whereas in the 6-methyl derivatives the conformer containing the 6-methyl group in axial position predominates. 相似文献
11.
Abstract The reaction of 2-mercapto-6,7,8,9-tetrahydro-3 H-benzo[4,5]thieno[2,3- d]pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3- d]-1,2,4-triazolo[4,5- a]pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3 H-benzo[4,5]thieno[2,3- d]pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride
to afford the non-isolable azo-coupling products which converted, in situ, to 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3- d]-1,2,4-triazolo[4,5- a]pyrimidin-5-ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some
of the newly synthesized compounds had a moderate effect against some bacterial and fungal species.
Graphical abstract
相似文献
12.
The title substances 1 and 2 were prepared by acylation of the corresponding ethyl 2-amino-thiophene- (or:-4,5,6,7-tetrahydro-benzo[ b]thiophene)-3-carboxylates, in some cases followed by reactions introducing a basic substituent.Additionally a group of 2-aroylamino-thiophene-(or:-4,5,6,7-tetrahydro-benzo[ b]thiophene)-3-carboxamides was subjected to ring closure reactions, yielding the corresponding 2-aryl-thieno[2,3- d]pyrimidin-4(3 H)-ones and 2-aryl-[1]benzothieno[2,3- d]pyrimidin-4(3 H)-ones (both: 3).
Zum Teil unter Mitarbeit von Ferdinand Fuhrmann 相似文献
13.
6-Allyl(diallyl, prop-2-yn-1-yl)amino-1-R-pyrazolo[3,4- d]pyrimidin-4(5 H)-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(6 H)-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(6 H)-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(6 H)-ones were converted into 8-methyl-1-R-imidazo[1,2- a]pyrazolo-[4,3- e]pyrimidin-4(5 H)-ones on heating to the melting point. 8-Methylidene-1-phenyl-7,8-dihydroimidazo-[1,2- a]pyrazolo[4,3- e]pyrimidin-4(6 H)-one underwent isomerization into linearly fused 6-methyl-1-phenyl-1,8-dihydro-4 H-imidazo[1,2- a]pyrazolo[3,4- d]pyrimidin-4-one on heating in sulfuric acid. 相似文献
14.
Antimony trichloride efficiently catalyses diastereoselective three-component reaction of urea, aromatic aldehydes and 2,3-dihydrofuran or 3,4-dihydro-2 H-pyran leading to 4-arylhexahydrofuro[2,3- d]pyrimidin-2(3 H)-ones and 4-arylhexahydro-1 H-pyrano[2,3- d]pyrimidin-2(8a H)-ones, respectively in good yield. 相似文献
15.
The reaction of 2-[( N-acyl, N-alkyl or phenyl)amino]-4 H-pyrido[1,2- a]pyrimidin-4-ones 8a-g with the N,N-dimethylformamide/phosphorus oxychloride Vilsmeier reagent 1 (95°, 90 minutes) afforded 1-alkyl or phenyl-2 H-dipyrido[1,2- a:2′,3′- d]pyrimidine-2,5(1 H) ?diones, 3-alkyl substituted or not, 10a-g . The starting compounds 8 were prepared by treating 2-amino-4 H-pyrido[1,2- a]pyrimidin-4-ones N-alkyl substituted 7a,b or N-phenyl substituted 4 with excess anhydrides (130°, 7 hours) when the 2-(alkylamino) derivatives 7 were used in the reaction, compounds 8 were obtained along with very small amounts of 3-acyl-2-(alkylamino)-4 H-pyrido[1,2- a]pyrimidin-4-ones 9 . 相似文献
16.
The following tetracyclic ring systems and their derivatives have been synthesized for pharmacological investigations: Trimethylenethieno[2,3— d]dihydropyrrolo[1,2— a]pyrimidin-4-one and -4-thione ( 1 a, 5 a); Tetramethylenethieno[2,3— d]dihydropyrrolo[1,2— a]pyrimidin-4-one and -4-thione ( 1 b, 1 j, 5 b); Pentamethylenethieno[2,3— d]dihydropyrrolo[1,2— a]pyrimidin-4-one and-4-thione ( 1 c, 5 c); Trimethylenethieno[2,3— d]tetrahydropyrido[1,2— a]pyrimidin-4-one and -4-thione ( 1 d, 5 d); Tetramethylenethieno[2,3— d]tetrahydropyrido[1,2,— a]pyrimidin-4-one and -4-thione ( 1 e, 5 e); Pentamethylenethieno[2,3— d]tetrahydropyrido[1,2— a]pyrimidin-4-one and -4-thione ( 1 f, 5 f); Trimethylenethieno[2,3— d]tetrahydroazepino[1,2— a]pyrimidin-4-one and -4-thione ( 1 g, 5 g); Tetramethylenethieno[2,3— d]tetrahydroazepino[1,2— a]pyrimidin-4-on and -4-thione ( 1 h, 5 h); Pentamethylenethieno[2,3— d]tetrahydroazepino[1,2— a]pyrimidin-4-one and -4-thione ( 1 i, 5 i); Tentamethylenethieno[2,3— d]tetrahydroazepino[1,2— a]pyrimidin-4-one ( 7 b); Pentamethylenethieno-[2,3— d]tetrahydropyrido[1,2— a]pyrimidin-4-one ( 7 c).Compounds 1 a–i were synthesized from 2-amino-3-ethoxycarbonyl-4,5-polymethylenethiophene 2 a–c with the corresponding lactim ethers ( 3 a–c) in chlorobenzene in the presence of polyphosphoric acid ( PPA). Compounds 7 b and 7 c were obtained in the reaction of -amino acid esters 2 b and 2 c with 2-bromopyridine ( 6). The thione derivatives ( 5 a–i) were prepared from compounds 1 a–i with phosphorus(V) sulphide.Part 74: Szabó J, Fodor L, Szcs E, Bernáth G, Sohár P (1984) Pharmazie 39: 347. 相似文献
17.
The reaction of 6-(R-amino)-5-acetyl-4-methylsulfonyl-2-phenylpyrimidines with amines was studied. 6-Arylamino derivatives react with alkylamines to form 6-alkylamino-4-arylamino-5-acetyl-2-phenylpyrimidines, which upon refluxing in benzene with dimethylformamide dimethylacetal are converted to 4-alkylamino-8-aryl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-ones. The cyclization proceeds selectively with participation of the arylamino group only, the alkylamino group being not involved. At the same time, refluxing of 5-acetyl-4,6-dibenzylamino-2-phenylpyrimidine with dimethylformamide dimethylacetal in toluene affords the product of condensation on the acetyl group, which upon refluxing in o-xylene transforms to 4-benzylamino-8-benzyl-2-phenylpyrido[2,3-d]pyrimidin-5(8H)-one. 相似文献
18.
One-step three-component cyclocondensation of 2,6-disubstituted pyrimidin-4(3 H)-ones with 1,3-dicarbonyl compounds and some aromatic and heterocyclic aldehydes on heating or under microwave irradiation afforded new functionally substituted 5,8-dihydropyrido[2,3- d]pyrimidin-4(3 H)-ones. Conventional heating was found to be more advantageous. The effects of the 2-substituent in the initial pyrimidin-4(3 H)-one and the nature of the dicarbonyl component on the product structure and yield were analyzed. 相似文献
19.
We describe an efficient synthesis of 2,4-substituted pyrido[4,3- d]pyrimidin-5(6 H)-ones, which involves the acid-promoted cyclization of cyano enamine 15 to afford 2,4-bis(methylthio)pyrido[4,3- d]pyrimidin-5(6 H)-one 17 as a key intermediate. Selective displacement of the 4-methylthio group by a wide range of anilines followed by oxidation of the 2-methylthio group and subsequent substitution by amines enabled the synthesis of a variety of 2,4-disubstituted pyrido[4,3- d]pyrimidin-5(6 H)-ones. 相似文献
20.
Heating of 5-acetyl-4-aminopyrimidine derivatives with ethyl acetoacetate, ethyl benzoylacetate, and diethyl acetone-1, 3-dicarboxylate in the absence of a base gave the corresponding 6-acylpyrido[2, 3- d]pyrimidin-7(8 H)-ones. Under analogous conditions, the reaction with ethyl malonate afforded ethyl 7-oxo-7, 8-dihydropyrido[2, 3- d]pyrimidine-6-carboxylates. The pyridone (rather than hydroxypyridine) structures of the pyridopyrimidines obtained were confirmed by IR spectroscopy.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 770–773, March, 2005. 相似文献
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