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1.
Aroylketenes, generated by the thermolysis of 5-aryl-2,3-dihydro-2,3-furandiones, react with S-methyl-N-cyano-N′-phenylisothiourea,
N-cyano-N′,N′-dimethylformamidine, and N,N-bis(β-cyanoethyl)-cyanamide with the formation of 6-aryl-2-[(methylthio)(phenylamino)methylene]amino-,
6-aryl-2-dimethylaminomethyleneamino-, and 6-aryl-2-[N,N-bis(β-cyanoethyl)amino]-4H-1,3-oxazin-4-ones respectively. Modeling
has been carried out of the interaction of benzoylketene with the indicated cyano compounds by the SSP MO LCAO semiempirical
method using the MNDO-PM3 approach. A mechanism is proposed for the formation of substituted 4H-1,3-oxazin-4-ones.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1490–1501, October, 2005. 相似文献
2.
Starting from 5-aryl-2,3-dihydro-2,3-furandiones and benzoyl cyanamide, 2-benzoylamino-6-aryl-1,3-oxazin-4-ones were obtained. It was shown that on reaction of o-chlorophenyl cyanamide with furandiones, 2-imino-3-(o-chlorophenyl)-5-phenacyliden-4-oxazolidones are formed which in acid medium rearrange to 3-(o-chlorophenyl)-5-phenacylideneimidazolidin-2,4-diones and on thermolysis in acid medium they form 2-(o-chloroanilino)-6-aryl-1,3-oxazin-4-ones.For Communication 39, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 166–169, February, 1985. 相似文献
3.
One-pot montmorillonite K-10 clay supported reactions of either salicylaldehyde/2-hydroxyacetophenone hydrazones and aryl-/alkylureas or salicylaldehydes/2-hydroxyacetophenone and 4-aryl-/alkylsemicarbazides expeditiously yield 3,4-dihydro-4-hydrazino-2H-benz[e]-1,3-oxazin-2-ones (9) via cycloisomerization of the intermediate salicylaldehyde/2-hydroxyacetophenone 4-aryl-/alkylsemicarbazones (5) under solvent-free microwave irradiation. Under the same conditions, hydrazines (9) readily underwent reductive dehydrazination on alumina-supported copper(II) sulfate to furnish 2H-benz[e]-1,3-oxazin-2-ones (10). 相似文献
4.
Intramolecular cyclization of acyl(ethoxycarbonyl)keteneN-benzoylaminals in boiling Ph2O gives 5-acyl-4-amino-2-phenyl-1,3-oxazin-6-ones.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1322–1323, July, 1995.This study was financially supported by the Russian Foundation for Basic Research (Grant No. 94-03-08964). 相似文献
5.
Volodymyr A. Sukach 《Journal of fluorine chemistry》2008,129(12):1180-1186
A cyclocondensation of disubstituted (thio)ureas and isocyanates derived from enantiomerically enriched 4-amino-4-aryl-5,5,5-trifluoropentan-2-ones affords a novel synthetic access to chiral 4-trifluoromethyl-substituted 3,4-dihydropyrimidin-2(1H)-(thi)ones and 3,4-dihydro-1,3-oxazin-2-ones, respectively. 相似文献
6.
Yu. S. Andreichikov D. D. Nekrasov M. A. Rudenko O. V. Vinokurova 《Chemistry of Heterocyclic Compounds》1989,25(9):1059-1061
Aroylketenes have been generated by thermolysis of 6-aryl-2,2-dimethyl-1,3-dioxin-4-ones. They take part in a 1,4-cycloaddition reaction at the CN bond of N-aryl or N,N-dialkyl-N-cyanoamines and of N'-phenyl-N-cyanoguanidine to form the corresponding 2-N-aryl-amino, 2-N,N-dialkylamino, and 2-N-phenylguanidino-6-aryl-1,3-oxazin-4-ones. p-Aminobenzonitrile and cyanoacetamide are acylated by aroylketenes to form the p-cyanophenylamide of p-toluylacetic acid and the cyano-acetamide of benzoylacetic acid.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1265–1268, September, 1989. 相似文献
7.
Bismethylthiomethylene Meldrum's acid reacts with amides in the presence of potassium hydroxide to afford methylthioacylaminomethylene Meldrum's acid 5. Aminolysis of 5 gives aminoacylaminomethylene Meldrum's acids 7. Thermolysis of 5 and 7 supplies a novel synthetic method of 4-methylthio- and 4-amino-2-aryl-6H-1,3-oxazin-6-ones. 相似文献
8.
V. N. Britsun A. N. Borisevich A. N. Esipenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2006,42(4):546-550
The products of cyclocondensation of 3-oxo-3-R1-N-R2-propanethioamides with 3-aryl-2-propenoyl chlorides in acetone in the presence of potassium carbonate are 5-acyl-1-aryl(alkyl)-4-aryl-6-thioxopiperidin-2-ones,
5-acyl-2-aryl-6-aryl(alkyl)amino-2,3-dihydro-4H-thiopyran-4-ones, and 2-acetonylidene-3,6-diaryl-5,6-dihydro-4H-1,3-thiazin-4-ones,
the structure of which is proven by both spectral methods and chemical conversions.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 623–628, April, 2006 相似文献
9.
E. S. Vostrov E. V. Leont'eva O. P. Tarasova A. N. Maslivets 《Russian Journal of Organic Chemistry》2004,40(7):1058-1061
Thermal decarbonylation of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones gives rise to intermediate aroyl(phenyl)ketenes which react with nonactivated Schiff bases, N,N'-dicyclohexylcarbodiimide, and p-di-methylaminobenzonitrile according to the [4 + 2]-cycloaddition pattern with formation of 6-aryl-5-phenyl-4H-1,3-oxazin-4-ones. Reactions of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones with activated Schiff bases at a temperature below the thermolysis temperature lead to 4-aroyl-4-phenyltetrahydropyrrole-2,3-diones. 相似文献
10.
Yu. S. Andreichikov D. D. Nekrasov M. A. Rudenko A. Yu. Konovalov 《Chemistry of Heterocyclic Compounds》1987,23(6):610-613
On reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with -aminoisobutyronitrile, o-aminobenzonitrile, and -anilinopropiononitrile, we obtained aroylpyruvic acid N-(1-methyl-1-cyanoethyl)-, N-(o-cyanophenyl)-, and N-phenyl-N-(cyanoethyl)-amides, respectively. On reaction of 5-aryl-2,3-dihydrofuran-2,3-diones with cyanoacetamide we obtained aroylacetic acid N-(cyanoacetyl)amides, while in the case of methyleneaminoacetonitrile and p-dimethylaminobenzonitrile we obtained (6-aryl-4-oxo-2,3-dihydro-1,3-oxazin-3-yl)acetonitriles and 2-(p-dimethylaminophenyl)-6-aryl-1,3-oxazine-4-ones, respectively.For Communication 2, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 740–743, June, 1987. 相似文献
11.
Catalytic ring-expanding carbonylation of 2-aryl-2-oxazolines is reported as a novel method for the synthesis of 4,5-dihydro-1,3-oxazin-6-ones. Various observations suggest the involvement of cobalt radicals as the catalytically active species. [reaction: see text] 相似文献
12.
T. V. Beryozkina N. N. Kolos V. I. Musatov V. D. Orlov 《Russian Chemical Bulletin》2006,55(6):1056-1059
3,4-Dihydrobenzo-1,4-oxazin-2-ones were obtained from the corresponding β-aroylacrylic acids and 2-aminophenols. With 2-amino-4(5)-nitrophenols,
stable intermediate β-amino adducts (4-aryl-4-oxobutyric acid derivatives) were isolated.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 6, pp. 1018–1021, June, 2006. 相似文献
13.
B. Yu. Lalaev I. P. Yakovlev N. N. Kuz’mich G. V. Ksenofontova V. E. Zakhs 《Russian Journal of General Chemistry》2010,80(10):2043-2047
Reactions of 2-alkylsulfanyl- and 2-alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones with oxygen-centered nucleophiles were studied. 2-Alkoxy-4-hydroxy-6H-1,3-oxazin-6-ones reacted with water and alcohols to give the corresponding alkyl 3-amino-3-oxopropanoates as a result of
opening of the oxazine ring at the C6-O bond, whereas their 2-alkylsulfanyl analogs turned out to be stable toward O-nucleophiles. The different reactivities of
the title compounds were interpreted in terms of quantum-chemical calculations of their electronic structure. 相似文献
14.
B. Yu. Lalaev O. A. Petina N. N. Kuz’mich I. P. Yakovlev G. M. Alekseeva V. E. Zakhs 《Russian Journal of General Chemistry》2006,76(4):645-648
4-Hydroxy-6H-1,3oxazin-6-ones exhibit properties of weak OH acids. These compounds are readily methylated with diazomethane to give the corresponding 4-methoxy derivatives. According to the potentiometric titration data, the pK a values of 2-methoxy-and 2-methylsulfanyl-substituted 4-hydroxy-6H-1,3-oxazin-6-ones range from 7.45 to 8.42, depending on the substituent in position 5 of the heteroring. 4-Hydroxy-6H-1,3-oxazin-6-ones in biological media exist mainly in the neutral form. 相似文献
15.
2a,4-Disubstituted 2,2a,3,4-tetrahydro-2-phenyl-1H-azeto[2,1-d][ 1,5]benzothiazepin-1-ones, as well as 2-substi-tuted 2,3-dihydro-3-phenylacetyl-2-styryl-benzothiazoles and 4a,6-disubstituted 3- .benzyl-4a,5-d/hydro-2-phenyl-1H,6H-[1,3]oxazino[2,3-d][1,5]benzothiazepin-1-ones, were obtained from the reaction of 2,4-disubstituted 2,3-dihydro-1,5-benzothiazepines with phenylacetyl chloride in the presence of triethylamine. The mechanism for the formation of 4a,5-dihydro-1H,6H-[1,3]oxazino[2,3-d][1,5]benzothiazepin-1-ones, 2,3-dihydro-1,3-oxazin-4-one derivatives, was suggested. 相似文献
16.
Yasuo Morita Masakazu Kaneko Sumiko Matsuzawa Yutaka Yamamoto 《Journal of heterocyclic chemistry》1997,34(2):515-519
Facile and convenient methods for the preparation of a variety of 2,6-disubstituted 4H-1,3-oxazin-4-ones 3 by three complementary methods are described. Treatment of the branched aliphatic imidate 2c,d with diketene 1 in the presence of a catalytic amount of acetic acid affords 2-substituted 6-methyl-1,3-oxazin-4-ones 3c,d , whereas the unbranched imidate 2b,e gave oxazines 3b,e and pyrimidines 4b,e (Method A). The reaction of acyl Meldrum's acid 5 with imidate 2 afford 2,6-disubstituted oxazine 3, though the alkylimidate with acetyl Meldrum's acid yielded 3 and 5-acetyl-1,3-oxazine-4,6-dione 8 (Method B). The cylodehydration of acylacetylcarboxamide 13 with acid, such as 70% perchloric acid or fluorosulfonic acid, afforded 1,3-oxazines 3 (Method C). 相似文献
17.
V. é. Zakhs I. P. Yakovlev N. A. Smorygo V. A. Gindin B. A. Ivin 《Chemistry of Heterocyclic Compounds》1987,23(3):325-332
1H,13C NMR, IR, and UV spectra have been studied for solutions of a number of potentially tautomeric 2-aryl-1,3-oxazine-4,6-diones and their 5-methyl substituted analogs with variation of substituent at the para position of the benzene ring, as well as compounds with a fixed structure that simulates possible tautomeric forms. The data have been compared with the results of quantum chemical calculations carried out in SSO MO LCAO approximation by the CNO, CNDO/2, and MPNDO/3 methods. In DMSO and THF solution the test compounds exist predominantly as 2-aryl-4-hydroxy-6H-1,3-oxazin-6-ones. The para substituent in the benzene ring does not affect the composition of the tautomer mixture significantly.For Communication 61, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 386–394, March, 1987. 相似文献
18.
Géza Stájer LászlÓ Mód Angela E. Szabó Ferenc Folöp Gábor Bernáth Pál Sohár 《Tetrahedron》1984,40(12):2385-2393
The -- amino acid with norbornene skeleton was converted into 2-aryvl---1,3-oxazin-4-ones -. These compounds, similarly to the isomers - studied by us earlier, undergo retrodiene decomposition under mild conditions to give 2-aryl-6-l,3-oxazin-6-ones (-) in 50-60% yield. The ratio of the decomposition rate constants of the tricyclic and -1,3-oxazin-4-ones, measured in toluene solution, is about 2. 相似文献
19.
Vostrov E. S. Leont'eva E. V. Tarasova O. P. Maslivets A. N. 《Russian Journal of Organic Chemistry》2003,39(1):103-107
Aroyl(phenyl)ketenes generated by thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones undergo [4+2]-cyclodimerization to 3-aroyl-6-aryl-3,5-diphenyl-3,4-dihydro-2H-pyran-2,4-diones. Heating of the latter leads to rearrangement with formation of 4-aroyloxy-6-aryl-3,5-diphenyl-2H-pyran-2-ones. Thermolysis of 5-aryl-4-phenyl-2,3-dihydrofuran-2,3-diones in the presence of carbonyl compounds yields 6-aryl-5-phenyl-4H-1,3-dioxin-4-ones. 相似文献
20.
A series of indole, thiophene and pyrrole-fused 1,3-oxazine-2,4-diones, 2-methyl-1,3-oxazin-4-ones and 2-dimethylamino-1,3-oxazin-4-ones were synthesized and evaluated as antitumor agents. 相似文献