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1.
New thietanyl-substituted derivatives of pyrimidine-2,4(1H,3H)-dione and imidazole were synthesized. The alkylation of 6-methylpyrimidine-2,4(1H,3H)-diones with 2-chloromethylthiirane in water involved the N1 atom of the pyrimidine ring and afforded 6-methyl-1-(thietan-3-yl)-pyrimidine-2,4(1H,3H)-diones. Under analogous conditions 6-aminopyrimidine-2,4(1H,3H)-dione gave rise to 6-(thietan-3-ylamino)pyrimidine-2,4(1H,3H)-dione. Unsymmetrically substituted 2-methyl-4(5)-nitro- and 5(4)-bromo-2-methyl-4(5)-nitro-1H-imidazoles reacted with 2-chloromethylthiirane to produce mixtures of isomeric 2-methyl-4(5)-nitro-1-(thietan-3-yl)-1H-imidazoles and 5(4)-bromo-2-methyl-4(5)-nitro-1-(thietan-3-yl)-1H-imidazoles. 相似文献
2.
V. A. Kataev S. A. Meshcheryakova V. V. Lazarev V. V. Kuznetsov 《Russian Journal of Organic Chemistry》2013,49(5):743-745
Reactions of 6-methylpyrimidine-2,4(1H,3H)-dione or 5-hydroxy-6-methyl-pyrimidine-2,4(1H,3H)-dione with 2-chloromethylthiirane afforded the corresponding substituted 1-(thietan-3-yl)pyrimidine-2,4(1H,3H)-diones. The calculations in the framework of approximations PBE/3z, B3LYP/6-31G++(d,p) and MP2/6-31G++(d,p) showed that the alkylation occurred at the atom N1 of the pyrimidine ring. 相似文献
3.
S. A. Meshcheryakova 《Russian Journal of General Chemistry》2014,84(8):1539-1542
A new approach to prepare 2-chloroacetamides has been developed, based on the reaction of chloroacetyl chloride with excess of secondary amines. Alkylation of 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-dione with the synthesized 2-chloroacetamides in the presence of potassium carbonate has afforded N 3-acetamido-substituted 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-diones. 相似文献
4.
S. A. Meshcheryakova V. A. Kataev D. A. Munasipova I. Ya. Fattakhova 《Russian Journal of General Chemistry》2014,84(5):865-868
Oxidation of 6-methyl-1-(thiethan-3-yl)pyrimidine-2,4(1H,3H)-dione, 5(6)-nitro-1-(thiethan-3-yl)-benzimidazole, 2-methyl-4-nitro-1-(thiethan-3-yl)- and 5-bromo-2-methyl-4-nitro-1-(thiethan-3-yl)imidazoles was examined. Corresponding 1-oxothietan-3-yl- and 1,1-dioxothietan-3-yl derivatives were synthesized for the first time. Some factors affecting the quality of the final products and optimal conditions of the oxidation of thietanyl derivatives of pyrimidine-2,4(1H,3H)-dione, nitrobenzimidazole, and nitroimidazole were found. According to 1H NMR spectroscopy data, the obtained sulfoxides are mixtures of cis/trans isomers, the diastereomers ratio determined by the substituent at position 3 of thietane ring. 相似文献
5.
Reaction of 2-[6-methyl-2,4-dioxo-1-(thietan-3-yl)-1,2,3,4-tetrahydropyrimidin-3-yl]acetic acid hydrazide with β-dicarbonyl compounds proceeds regioselectively; the structure of the formed hydrazones is governed by the structure of the β-dicarbonyl reaction component. The reaction with acetyl- and propionylacetone afforded 3-[2-(5-alkyl-3-methyl-1H-pyrazol-1-yl)-2-oxoethyl]-6-methyl-1-(thietan-3-yl)pyrimidin-2,4(1H,3H)-diones, with aroylacetones, 5-hydroxypyrazoline derivatives which are present in DMSO solutions in E′ conformation with respect to the amide bond. The condensation products with acetoacetic acid derivatives have a linear structure and consist of mixtures of E,Z- and E′,Z′-isomers owing to the geometric and conformational isomerism. 相似文献
6.
O. M. Lezina S. A. Rubtsova V. A. Polukeev A. V. Kutchin 《Russian Journal of Organic Chemistry》2012,48(9):1222-1225
Oxidation of 3-methyl-2-sulfanylquinazolin-4(3H)-one with chlorine dioxide under different conditions gave 2,2??-disulfanediylbis[3-methylquinazolin-4(3H)-one], 3-methyl-4-oxo-3,4-dihydroquinazoline-2-sulfonic acid, 3-methylquinazoline-2,4(1H,3H)-dione, 6-chloro-3-methylquinazoline-2,4(1H,3H)-dione, and N,N-diethyl-3-methyl-4-oxo-3,4-dihydroquinazoline-2-sulfonamide. 相似文献
7.
Michihiko Noguchi Kazushige Sakamoto Seiji Nagata Shoji Kajigaeshi 《Journal of heterocyclic chemistry》1988,25(1):205-208
6,7-Dihydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-diones were obtained in high yields from the reaction of 5-formyl-1,3,6-trimethylpyrimidine-2,4(1H,3H)-dione ( 1 ) and primary amines. For this pyridopyrimidine synthesis the following reaction pathway is proposed; the [1,5]-hydrogen shift of 1 gives a 5,6-dihydro-5,6-dimethylenepyrimidine-2,4(1H,3H)-dione intermediate. The cycloaddition reaction of the intermediate with aldimines from 1 and the primary amines affords 5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine-2,4(1H,3H)-diones, which are dehydrated to the final products. 相似文献
8.
Larry T. Pierce 《Tetrahedron》2010,66(51):9754-9761
2,3-Bis(1-methyl-1H-indol-3-yl) methyl-3-oxopropionate is a key intermediate in the synthesis of a new family of LY333531 analogues. Base-mediated cyclocondensation with thiourea afforded novel 5,6-bis(1-methyl-1H-indol-3-yl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one, which was efficiently converted to the pyrimidin-2,4(1H,3H)-dione congener. Synthesis of a six-membered K-252c analogue, 5,6-bis(1-methyl-1H-indol-3-yl)pyrimidin-4(3H)-one, is also described. 相似文献
9.
N. I. Makarova E. N. Shepelenko O. G. Karamov A. V. Metelitsa V. A. Bren’ V. I. Minkin 《Russian Chemical Bulletin》2014,63(1):109-114
New nonsymmetrical dihetarylethenes, 3-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)-4-(3-thienyl)furan-2,5-dione and 1-alkyl- and (1-aryl)-3-(1-benzyl-5-methoxy-2-methyl-1H-indol-3-yl)-4-(3-thienyl)-1H-pyrrole-2,5-dione, exhibiting photochromic properties in solutions were synthesized. Noncyclic isomers of dihetarylethenes show fluorescence with quantum yields up to 0.13. 相似文献
10.
Oxidation of 2H, 6H-thiin-3-ones 1a – c with 3-chloroperbenzoic acid affords the corresponding 1-oxides 2a – c . On irradiation (350 nm) in either benzene or MeCN, these cyclic sulfoxides 2 isomerize to 3H, 7H-1,2-oxathiepin-4-ones 3 . The tetramethyl derivative 3a is isolated by flash chromatography at ?10°, but, at higher temperatures, it undergoes ring contraction and H2O elimination to give 4,4-dimethyl-2(2-methylprop-2enylidene)thietan-3-one ( 4 ). Diemthyloxathiepinones 3b and 3c undergo ring contraction in MeOH to afford 1-(4-methylthiophen-2-yl)ethanone ( 5 ) and two diastereoisomeric 4,4-dimethyl-2-methoxy-2-(1-methoxyethyl)thietan-3-ones ( 6 and 7 , respectively). 相似文献
11.
R. F. Papoyan L. A. Khachatryan G. A. Panosyan V. T. Kochikyan 《Russian Chemical Bulletin》2012,61(8):1656-1658
The bromination of 6,7-dihydro-1H-cyclopenta[d]pyrimidine-2,4(3H,5H)-dione (1) resulted in the substitution in the aliphatic ring. The reaction of this product with different N-nucleophiles gives new derivatives of the starting compound. The direction of the substitution in the alicycle was established by studying further transformations of some of these compounds by means of NMR spectroscopy. 相似文献
12.
Franco Gatta Maria Rosaria Del Giudice Anna Borioni Carlo Mustazza 《Journal of heterocyclic chemistry》1994,31(1):81-86
Synthesis of 1,3-dipropyl-1H,3H-pyrazino, pyrido, pyrimido and pyrrolo[2,1-f]purine-2,4-diones, starting from 5,6-diamino-1,3-dipropylpyrimidine-2,4-dione 1 and 6-chloro-1,3-dipropylpyrimidine-2,4-dione 14 is described. A new synthetic approach to 1,3-dipropyl-1H,3H-pyrido(or pyrazino)[1′,2′-1,2]pyrimido[4,5-d]pyrimidine-2,4,5-triones 19 e, f, h has been also developed. 相似文献
13.
V. O. Koz’minykh V. I. Goncharov E. N. Koz’minykh 《Russian Journal of Organic Chemistry》2006,42(11):1715-1718
A simple preparative procedure was developed for 3-(2-oxoalkylidene)-3,4-dihydroquinoxalin-2(1H)-ones, 4,5-dihydroxy-1-[3-oxo-3,4-dihydroquinoxalin-2(1H)-ylidene]-3,5-octadiene-2,7-dione, and 3-(2,3-dihydroxy-4-methyl-5-oxo-1,3-cyclopentadien-1-yl)quinoxalin-2(1H)-one by reaction of methyl ketones first with diethyl oxalate in the presence of sodium, and then with o-phenylenediamine. 相似文献
14.
Pengfa Li Chuanlang Zhan Shanlin Zhang Xunlei Ding Fengqi Guo Shenggui He Jiannian Yao 《Tetrahedron》2012,68(43):8908-8915
In this paper we report synthesis of a series of aromatic fused pyrimidine-2,4(3H)-dione-1-yl acetic acid and new PNA monomers containing these polycyclic nucleobase analogues. Introduction of a fused aromatic ring onto the 5,6-positions of the pyrimidine-2,4-[1H,3H]-diones brings about the steric effects and the charge delocalization, both weakening the nucleophilic substitutions on the 1- and 3-positions. We found that alkali metal cations play an important role in this alkylation reaction. LiOH brings out a much more efficient alkylation than NaOH does, while KOH nearly does not work on this reaction. Such influences from the alkali metal cations are probably due to that the charge-pairing interactions between the pyrimidine-2,4-dioxide anions and the alkali metal cations rearrange the charge distribution around the whole aromatic system and increase the negative charge distribution on the 1- and 3-nitrogen atoms, which then strengthens the nucleophilic reactivity on these positions. 相似文献
15.
Addition of 6-methyl-2-(3-methyl-5-oxo-2,5-dihydropyrazol-1-yl)pyrimidin-4(1H)-one, a compound with two CH-acidic centers, to 5-benzylidenepyrimidine-2,4,6(1H,3H,5H)-trione proceeds with the participation of the atom C5 of pyrimidine ring. Under the realized reaction conditions the latter possesses a greater nucleophilicity as a result of
the priority ionization. The obtained Michael adduct is unstable in the neutral aqueous medium and is decomposed into initial
oxopyrazolylpyrimidinone, pyrimidine-2,4,6-(1H,3H,5H)-trione, and benzaldehyde. 相似文献
16.
Refaah A. Alshahrani Adil A. Gobouri Naif A. Alshanbari Saleh A. Ahmed 《Phosphorus, sulfur, and silicon and the related elements》2018,193(6):345-349
The targeted synthesis of 2-(methylsulfanyl)-6-(furan-2-yl)-4(3H)-selenoxo -pyrimidine-5-carbonitrile failed due to the formation 1-methyl-2-methylsulfanyl-6-oxo -4-(furan-2-yl)-1,6-dihydropyrimidine-5-carbonitrile. A new series of 5,6,7,8-tetrahydro-1-benzo thieno[2,3-d]pyrimidine-4-yl substituted selanyl derivatives were prepared by the reaction of sodium diselenide with 4-chloro-5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidine followed by the reaction with chloroacetic acid derivatives such as ethyl chloroacetate, chloroacetamide or chloroacetonitrile. Hydrazinolysis of ethyl (5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidine- 4-ylselanyl)acetate with hydrazine hydrate gave the corresponding hydrazino derivative. The latter reacted with ethyl acetoacetate, acetylacetone, diethyl malonate, ethoxymethylenemalononitrile or ethyl 2-cyano-3-ethoxyacetate to afford 5-methyl-2-[2-(5,6,7,8-tetrahydro-1-benzothieno [2,3-d]pyrimidine-4-ylselanyl)acetyl]-2,4-dihydropyrazol-3-one, 1-(3,5-dimethylpyrazol-1-yl)-2- (5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4-ylselanyl)ethanone, 1-[2-(5,6,7,8-tetrahydro -1-benzothieno[2,3-d]pyrimidine-4-ylselanyl)acetyl]-2,4-dihydropyrazolidine-3,5-dione and 5-Amino-1-[2-(5,6,7,8-tetrahydro-1-benzothieno[2,3-d]pyrimidin-4-ylselanyl)acetyl]-1H-pyrazol -4-yl substituted carbonitrile or ethyl carboxylate, respectively. The structure of the novel compounds was confirmed by spectroscopic tools (IR, 1H NMR 13C NMR and mass spectra) and elemental analysis. 相似文献
17.
T. Sudhakar Rao Ganapathi R. Revankar Ravi S. Vinayak Roland K. Robins 《Journal of heterocyclic chemistry》1992,29(2):343-354
The synthesis of the congeners of uridine and cytidine in the pyrazolo[4,3-d]pyrimidine and pyrrolo[3,2-d]-pyrimidine ring system is described. Glycosylation of the trimethylsilyl (TMS) derivative of pyrazolo[4,3-d)pyrimidine-5,7(1H,4H,6H)-dione (4) with either 1-bromo- or 1-O-acetyl-2,3,5-tri-O-benzoyl-D-ribofuranose 5 and 6 , respectively in the presence of a Lewis acid catalyst gave the protected nucleoside 7 , which on debenzoylation afforded the uridine analogue 4-β-D-ribofuranosylpyrazolo[4,3-d]pyrimidine-5,7(1H,6H)-dione (8). Thiation of 7 gave 13 , which on deprotection yielded 4-β-D-ribofuranosyl-5-oxopyrazolo[4,3-d]pyrimidine-7(1H,-6H)-thione (14). Ammonolysis of 13 gave a low yield of the cytidine analogue 15. A chlorination of 7 , followed by amination furnished an alternative route to 15. A similar glycosylation of TMS-4 with 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride (16) gave mainly the N4 glycosylated product 17 , which on debenzylation furnished 4-β-D-arabinofuranosylpyrazolo[4,3-d]pyrimidine-5,7(1H,6H)-dione (18). 7-Amino-4-β-D-arabinofuranosylpyrazolo[4,3-d]pyrimidin-5(1H)-one (23) was prepared from 17 via the pyridinium chloride intermediate 21. Condensation of the TMS derivative of pyrrolo[3,2-d]pyrimidine-2,4(1H,3H,5H)-dione (24) with 6 , followed by deprotection of the reaction product gave 1-β-D-ribofuranosylpyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (26). Similarly, TMS-24 was reacted with 16 to give a mixture of the blocked nucleosides 31 and 32 , which on debenzylation afforded a mixture of two isomeric compounds 34 and 35. 1-β-D-Arabinofuranosylpyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (34) was converted to the ara-C analogue 38 via the 3-nitrotriazolyl intermediate 36. The structure of 38 was confirmed by single crystal X-ray diffraction studies. 相似文献
18.
Some 6-(1H-1,2,3-triazol-1-yl)pyrimidine-2,4(1H,3H)-dione derivatives were synthesized via the reaction of 6-azido-1,3-dimethyluracil
with ethyl acetoacetate in the presence of sodium ethoxide. The antiviral activities of these compounds against Hepatitis
A virus (HAV, MBB-cell culture adapted strain) and Herpes simples virus type-1 (HSV-1) were tested. 相似文献
19.
5-Hydroxy uracils or 4-hydroxy[1]benzopyran-2-ones were refluxed with 2-bromobenzyl bromides in acetone in the presence of anhydrous potassium carbonate to afford a number of 5-(2′-bromobenzyloxy) pyrimidine-2,4-dione (80-92%) or 4-(2′-bromobenzyloxy) benzopyran-7-ones (70-82%) respectively. These were then refluxed with tri-n-butyltin chloride and sodium cyanoborohydride in the presence of a catalytic amount of azobisisobutyronitrile (AIBN) for 3-4 h to give 1H,3H,6H [2]benzopyrano[4,3-d]pyrimidine-2,4-diones (75-85%) or 12H-benzopyrano[3,2-c][1]benzopyran-5-ones (70-85%) respectively. 相似文献
20.
Yu. L. Zborovskii V. V. Orysyk V. I. Staninets V. V. Bon’ 《Russian Journal of Organic Chemistry》2011,47(6):881-885
Cyclization of 2-(2-{4-[allylamino(thioxo)methyl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione by the action of iodine, bromine, or sulfuryl chloride gave 2-(2-{4-[4,5-dihydro-5-(halomethyl)-thiazol-2-yl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione hydrohalides which were converted into 2-{2-[4-(5-methylthiazol-2-yl)piperazin-1-yl]ethyl}-1H-benzo[de]isoquinoline-1,3(2H)-dione. 相似文献