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1.
Mou-Yung Yeh Fat-Fong Chan Hsien-Ju Tien Toshio Fuchigami Tsutomu Nonaka 《中国化学会会志》1989,36(2):143-148
N-Hydroxy-3-arylsydnone-4-carboxamide oximes (7) were prepared from the corresponding 3-arylsydnone-4-carbohydroximic acid chlorides (6) and hydroxylamine in high yield. The chemical reactivity of compound (2) is somewhat different from 3-arylsydnone-4-carboxamide oximes (2) in that the former compounds reacted with both aromatic and aliphatic aldehydes in the presence of acid catalyst to give 3-aryl-4-(5-aryl-1,2,4-oxadiazol-3-yl)sydnones (5) and 3-aryl-4-(5-alkyl-1,2,4-oxadiazol-3-yl)sydnones (3). 相似文献
2.
I. M. Bazavova V. N. Britsun A. N. Esipenko V. M. Neplyuev M. O. Lozinsky 《Chemistry of Heterocyclic Compounds》2000,36(9):1058-1061
Reaction of 4-aryl-1,2,4-triazolidine-3,5-dithiones in an alkaline medium with chloroacetic acid and its derivatives, as well as with -bromo ketones, results in their conversion to 4-aryl-1,2,4-triazole-3,5-bis(sulfides). The aminomethylation in a neutral medium leads to the formation of 1-(aminomethyl)-4-aryl-1,2,4-triazolidine-3,5-dithiones. 相似文献
3.
In the presence of base, 3-subslituted 4-fonnyl- and 4-acetylsydnones decarbonylated to afford the corresponding 3-substituted sydnones. The Claisen-Schmidt reaction occurred between 3-substituted 4-for-mylsydnones and methyl ketone (such as 4-acetylsydnones, acetone and acetophenone) in dilute basic solution or electrogenerated basic (EGB) solution. 相似文献
4.
N. Yu. Gorobets A. V. Borisov A. V. Silin V. M. Nikitchenko S. N. Kovalenko 《Chemistry of Heterocyclic Compounds》2002,38(11):1389-1396
The reaction of 3-(4-aryl-2-thiazolyl)- and 3-(2-benzothiazolyl)-2-iminocoumarins with N-nucleophiles was studied. This reaction gives 2-N-substituted 3-(4-aryl-2-thiazolyl)- and 3-(2-benzothiazolyl)iminocourmarins. N-Nucleophiles such as arylamines, heterocyclic amines, and hydrazine derivatives undergo this reaction. 相似文献
5.
3-Aryl-4-(5-aryl-Δ2-1,2,4-oxadiazolin-3-yl)sydnones (5) were synthesized in high yields by the reaction of 3-arylsydnone-4-carboxamide oximes (prepared from the corresponding 3-arylsydnone-4-carbonitriles) with aromatic aldehydes in the presence of acid catalysts. No reaction occurred when aliphatic aldehydes were used. The oxadiazolin-3-ylsydnones (5) were easily converted into the corresponding 3-aryl-4-(5-aryl-1,2,4-oxadiazol-3-yl)sydnones by N-bromosuccinimide oxidation. The 3-arylsydnone-4-carbonitrile oxides were synthesized in good yields by N-bromosuccinimide oxidation of the corresponding 3-arylsydnone-4-carboxaldehyde oximes. 相似文献
6.
The crystal and molecular structures of three sydnone derivatives are reported. The compound 3-cyclohexylsydnone crystallizes in space group C2/c of the monoclinic system with sixteen molecules in a cell of dimensions a = 19.326 (3), b = 9.471 (2), c = 20.005 (4)Å, β = 106.85(1)°. The structure has been refined to a final value of 0.0581 for the conventional R-factor based on 2222 independent observed intensities. Form I of 3-(3-pyridyl)sydnone crystallizes in space group P2/n of the monoclinic system with eight molecules in a cell of dimensions a = 7.317(2), b = 9.283 (2), c = 20.891 (6) Å, β = 99.61(2)°. The structure has been refined to a final value of 0.0514 for the conventional R-factor based on 1208 independent observed intensities. Form II of 3-(3-pyridyl)sydnone crystallizes in space group P21/c of the monoclinic system with eight molecules in a cell of dimensions a=9.073 (2), b = 22.267 (5). c = 7.494(2)Å, β = 112.15 (2)°. The structure has been refined to a final value of 0.0462 for the conventional R-factor based on 1330 independent observed intensities. Each of the three structures contains two crystallographically independent molecules in the cell. In the case of 3-cyclohexylsydnone, one of the independent molecules exhibits disorder around the exocyclic bond at N(3). A comparison of bond lengths indicates that the (electron donating) cyclohexyl group brings about enhanced electron density in the N(3)-C(4) bond, and possibly in the N(3)-N(2) bond. All three structures studied here exhibit intermolecular hydrogen bonding involving C(4)-H(4)…O(6) interactions. Although there are no stacking interactions in the cyclohexyl derivative, there is evidence for such interactions in the 3-pyridyl derivatives. 相似文献
7.
Under various basic solutions and reaction durations, 3-substituted 4-formyIsydnones and nitroalkanes containing α-active hydrogen (e.g. nitromethane and nitroethane) are converted to β-nitroalcohols, nitroalkenes and dinitroalkanes. β-Nitroalcohols are obtained only by electrochemical reaction on an electrogenerated base (EGB). The mechanism of overall reaction steps in particular is discussed. 相似文献
8.
Hsien-Ju Tien Yan-Hong Tsai Wen-Yuan Yeh Jong-Chuan Yeh Yaw-Kuen Lee Young-Shang Ho 《中国化学会会志》1990,37(1):79-84
Two new sydnones; 3-(o-methoxybenzyl)sydnone(1) and 3-(o-melhoxybenzyl)-4-morpholinomethylsydnone(2) were synthesized from o-methoxybenzylamine and ethyl bromoacetat in moderate yields. 3-(o-,m-,p-Fluorophenyl)sydnones were prepared from the corresponding fluoroaniline and chloroacetic acid in higher yields with a conventional method. From the biological activity test, 1 shows significant response of coronary dilation test, collagen induced platelet aggregation inhibition, local anesthetic and moderate cardiotropic activity. In addition, 1 also leads to anticonvuls, muscle relaxation and behavior depression. But 2 only shows inhibition of collagen induced platelet aggregation and antiwrithing. 3-(p-Fluorophenyl)sydnone (5) shows significant response of coronary dilation, collagen induced platelet aggregation inhibition, moderate cardiotropic activity, antiwrithing and local anesthetic But 3-(o-Fluorophenyl)sydnone(3) and 3-(m-fluorophenyl)sydnone(4) only show coronary dilation and moderate cardiotropic activity. 相似文献
9.
A convenient method to prepare 4-formyl-3-arylsydone (I) from 3-arylsydnone by the Vilsmeier reaction in moderate yields (30%-76%) was carefully investigated. According to the Schmidt reaction, I reacts with sodium azide in concentrated sulfuric acid to produce 3-arylsydnone-4-carboxamide (II). But 3-arylsydnone-4-carhonitrile (III) is obtained, if dilute sulfuric acid was used instead. When III treates with concentrated sulfuric acid, II is obtained in good yield. The all possible reaction mechanisms are suggested. 相似文献
10.
The 13C NMR spectra of twelve 3-aryl-4-(5-aryl-Δ2-l,2,4-oxadiazolin-3-yl)sydnones and twelve 3-aryl-4-(5-aryl-l,2,4-oxadiazol-3-yl)sydnones have been measured and assigned by means of proton-noise decoupling and DEPT-experiments. The coupling constants were determined by means of gated decoupling, and NOE effects were observed by comparison of proton-decoupled and inverse-gated decoupled spectra. Differences shown by the oxadiazoline and the oxadiazole rings and the substitution effects are discussed. 相似文献
11.
Cyclization were occurred via the coupling reactions of some mercuric chloride derivatives of sydnone with LiPdCl3-CuCl2. A unique six-membered ring, 3,3′-ethylene-4,4′-bissydnone, was obtained by the cyclization reation of 1,2-di[3-(4-chloromercuric)sydnonyl]ethane. However, the seven-membered 3,3′-trimethylene-4,4′-bissydnone and 1,3-di[3-(4-chloro)sydnonyl]-propane were obtained from the corresponding mercuric chlroide of sydnone. Onyl substitution reaction took place when 4,4′-di[3-(4-chloromercuric)sydnonyl]biphenyl, 4,4′-di[3-(4-chloromercuric)sydnonyl]benzene, di(p-[3-(4-chloromercuric)sydnonyl]-phenyl}methane and, di(p-[3-(4-chloromercuric)sydnonyl]phenyl]ether were treated using the same process. 相似文献
12.
3-Arylsydnone-4-carbonitrile oxides (2), which are generated in situ by thermal dehydrochlorination of the corresponding hydroximic acid chlorides (1), undergo 1,3-dipolar cycloadditions with sydnone-4-carbonitriles (6) to give 3-aryl-4-[5-(3-arylsydnonyl)-1,2, 4-oxadiazol-3-yl] sydnones (9). These nitrile oxides (2) also react with alkyl- and arylnitriles to give 1,3-dipolar cycloaddition products. 相似文献
13.
Hsien-Ju Tien Mou-Yung Yeh Ded-Shih Huang Yi-Lung Wu Wen-Fa Kuo Wen-Kuen Chang Jing-Chyi Chang 《中国化学会会志》1998,45(3):387-390
3-(3′-,4′-Hydroxyphenyl)sydnones were prepared by dealkylation of 3-(3′-,4′-alkoxyphenyl)sydnones with concentrated sulfuric acid at room temperature in a range of 59 to 86% yield. 相似文献
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18.
Sixteen 3-aryl-4-oxo-2-phenyl-4,5,6,7-tetrahydroindazoles were obtained from the reaction of the phenylhydrazones of dimedone
and cyclohexane-1,3-dione with 3-bromo-, 4-bromo-, 4-chloro-, 4-fluoro-, 2-hydroxy-, 4-hydroxy-, 4-methoxy-, 2-nitro-, 3-nitro-,
4-nitro-, and 4-dimethylamino-benzaldehydes. The interaction of the tosylhydrazones of dimedone and cyclohexane-1,3-dione
with the substituted benzaldehydes gave thirteen 3-aryl-4-oxo-4,5,6,7-tetrahydroindazoles.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1662–1668, November 2005. 相似文献
19.
The reactions of 1-aryl-4-hydrazinocarbonyl-2-pyrrolidinones with 2,4-pentanedione and 2,5-hexanedione have been studied.
It was found that heating the hydrazinocarbonyl compounds with 2,4-pentanedione gave 3,5-dimethylpyrazole compounds and with
2,5-hexanedione gave 1-substituted 2,5-dimethylpyrroles.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 229–232, February, 2008. 相似文献
20.
3-Arylsydnone-4-carbonitrile oxides may undergo 1,3-dipolar cycloadditions with alkenes to produce the corresponding 3-aryl-4-(5-substituted-isoxazolin-3-yl)sydnones. The direct reaction of 3-arylsydone-4-carbohydroximic acid chlorides with alkenes may also give the same products, and with higher yield. 相似文献