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1.
Wittig condensations of both stabilized and unstabilized ylides were successfully achieved with 2-acetamido-4-hydroxy-5-phenylbutylpyrimidine-6-carboxaldehyde (XI); functionalized Wittig reagents derived from dichloroacetone, ethyl 4-iodobutyrate, 4-bromobutyronitrile, phenylpropyl bromide, 3-bromopropylphthalimide, p - nitrobenzyl bromide, and p-nitrocinnamyl bromide were used. The resultant 6-substituted pyrimidines could be further transformed by reduction of the 6-side-chain double bond. Successful Wittig reactions were achieved with XI where the corresponding 2-amino-4-hydroxy-5-phenylbutylpyrimidine-6-carboxaldehyde (X) with its less electrophilic aldehyde group failed to give isolable yields of condensation products. 相似文献
2.
2-Amino-6-bromomethyl-5-phenylbutyl-4-pyrimidinol (IV) smoothly alkylated triphenyl phosphine, resulting in a 95% yield of the phosphonium salt (V). This Wittig reagent (V) readily condensed with p-nitrobenzaldehyde, p-nitrocinnamaldehyde, or cinnamalde-hyde in N,N-dimethylformamide to give the 6-(p-nitrostyryl) (X), 6-(p-nitrophenyl-1,3-butadien-1-yl) (VIH), and 6-(phenyl-1,3-butadien-1-yl) (IX) pyrimidinols in 72, 67 and 44% yields, respectively. Catalytic reduction of VIII and IX afforded the corresponding 6-(p-aminophenylethyl) (XII) and 6-(p-aminophenylbutyl) (XI) 4-pyrimidinols. 相似文献
3.
M. Mirza-Aghayan N. Mohammadian M. Abolghasemi Malakshah R. Boukherroub A. A. Tarlani 《Journal of the Iranian Chemical Society》2013,10(3):559-563
A simple and efficient approach towards one-step synthesis of 2-amino-5-cyano-4-hydroxy-6-aryl pyrimidines has been developed. It is based on three-component condensation of aliphatic, aromatic or heterocyclic aldehydes, ethyl cyanoacetate and guanidinium carbonate in the presence of amino-functionalized SBA-15 catalyst in ethanol. In this chemical process, the tautomeric interconversion of pyrimidine derivatives has been observed. This efficient technique has the advantage to give 2-amino-pyrimidine derivatives using a heterogeneous catalyst in high yields, to be completed in short reaction times and to offer a simple product isolation procedure. 相似文献
4.
Methods for the synthesis of 5-cyano-7-hydroxy-2-carboxybenzofurans bearing a variety of substituents at the 6-position are outlined. The scope and limitations of lithiation processes, electrophilic substitutions, and pericyclic reactions are investigated. 相似文献
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Leonardo Bonsignore Maria Teresa Cocco Giuseppe Loy Valentina Onnis 《Journal of heterocyclic chemistry》1992,29(1):237-239
The reaction of 2-cyanoacetamidines 1 with carbon suboxide 2 afforded 6-amino-4-hydroxy-2(1H)-pyri-dones 4 . Compounds 4 were also obtained by reaction of amidines 1 and 2,4,6-trichlorophenylmalonates 3 . 相似文献
8.
The synthesis of 2-amino-4-hydroxy-6-amyl-1,3,5-triazanaphthalene (8) is described as a model sequence pertinent to preparation of 8-deazafolic acid and its analogs. Condensation of 2-acet-amido-4-hydroxy-6-pyrimidinealdehyde (3) with dimethyl 2-oxoheptylphosphonate afforded 1-(2′-acetamido-4′-hydroxy-6′-pyrimidinyl)-1-octene-3-one (4) as a key intermediate. Conversion of 4 to 1-(2′-amino-4′-hydroxy-5′ -phenylazo-6′ pyrimidinyl)-3-octanone (7) followed by reductive cyclization yielded 8 or its tetrahydro derivative (9) . 相似文献
9.
The Wittig reaction of quinisatines ( 1a,b ) with 1-ethoxycarbonylethyliden- ( 2a ) and ethoxycarbonylmeth-ylenetriphenylphosphorane ( 2b ) has been investigated. In both cases unusual reaction products ( 3a,b and 12a,b respectively) were isolated in high yields and converted to potential antiinflammatory acids 6, 8, 15 and lactones 4 , 7. 相似文献
10.
L. S. Stanishevskii I. G. Tishchenko V. I. Tyvorskii L. A. Khil'manovich 《Chemistry of Heterocyclic Compounds》1975,11(5):519-522
Esters of 5-amino-4-hydroxy-3-methylvaleric acids, which exist as pairs of diastereomers and are readily converted to the corresponding methyl-substituted 4-aminomethyl-4-butanolides or 5-hydroxy-2-piperidones, are obtained by reaction of esters of 3-methyl-4, 5-epoxy-2-pentenoic acid with amines and subsequent hydrogenation of the resulting esters of 5-amino-4-hydroxy-3-methyl-2-pentenoic acids.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 5, pp. 594–598, May, 1975. 相似文献
11.
An efficient Heck coupling of 2-hydroxy-3-iodo-naphthoquinone with a series of electron-deficient alkenes in aqueous solution has been accomplished. The method is characterized by simple conditions and facile work-up to isolate the products in good to excellent yields. The products contain the motif present in several naphthoquinone pigments but with enhanced polarity. 相似文献
12.
Bruno Cavalleri Piero Bellani Giancarlo Lancini 《Journal of heterocyclic chemistry》1973,10(3):357-362
Treatment of 4(5)-phenyl(or alkyl)-2-aminoimidazoles with isoamyl nitrite in acetic acid afforded the corresponding 4(5)-substituted 2-amino-5(4)-hydroxyimino-5(4)H-imidazoles which by heating in water were transformed into 3-benzoyl(or acyl)-5-amino-1,2,4-oxadiazoles. 相似文献
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A total synthesis of 5-vinyl pyrimidine and some of its substituted derivatives is described. The following vinyl pyrimidines have been prepared: 5-vinyl pyrimidine, 5-vinyl-4,6-dimethoxy pyrimidine, 5-(α-bromo) vinyl-4,6-dimethoxy pyrimidine. 相似文献
15.
Akimori Wada Junpei Yamamoto Yuka Hamaoka Kazuhiro Ohki Sotoo Nagai Sh
ichi Kanatomo 《Journal of heterocyclic chemistry》1990,27(6):1831-1835
ortho-Directed lithiation of some pyrimidines has been investigated. Treatment of 2- and/or 4-alkoxy or acylaminopyrimidine with lithium 2,2,6,6-tetramethylpiperidide in ether at 0°, followed by quenching with various electrophiles afforded the corresponding 5-substituted pyrimidines. 相似文献
16.
L. S. Vasil'ev F. E. Surzhikov O. G. Azarevich V. S. Bogdanov V. A. Dorokhov 《Russian Chemical Bulletin》1996,45(11):2574-2577
Schemes for synthesizing 3-acyl-4-amino(hydroxy)-2-trifluoromethylpyridines from 3-acyl 4-amino-5,5,5-trifluoro-3-penten-2-ones via their diphenylboron chelate complexes have been suggested.Translated fromlzvestiyn Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2715–2718, November, 1996, 相似文献
17.
Synthesis of the novel 2-halogenated 4-amino-5-pyrimidinecarbonitriles 3a,b starting from ethoxy-methylenemalononitrile 1 and cyanamide is described. Nucleophilic substitution of the reactive halogen atom leads to the derivatives 5a-g, 6 and 7a-h. 相似文献
18.
A new simple method has been used to prepare 6-substituted 4-(subst. amino)-5-aryldiazenyl-1-arylpyridazinium salts from N-methyl- or N-aryl-3-amino-1-phenylbut-2-en-1-ones and 4-aminopent-3-en-2-ones and substituted benzenediazonium tetrafluoroborates or hexafluorophosphates. The structure of selected derivatives was studied by means of 15N NMR spectra and X-ray. 相似文献
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Synthesis of 4-amino-6-hetarylthieno[2,3-d]pyrimidines from 5-acetyl-6-aminopyrimidine-4(3H)-thiones
Komkov A. V. Baranin S. V. Dmitrenok A. S. Zavarzin I. V. 《Russian Chemical Bulletin》2022,71(8):1720-1728
Russian Chemical Bulletin - An efficient method for the synthesis of functionalized thieno[2,3-d]pyrimidines and 2-(thieno[2,3-d]pyrimidin-6-yl)pyrido[2,3-d]pyrimidines from... 相似文献