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1.
Bond-switching rearrangement via hypervalent sulfur occurs during the reactions of 5-anilino-2-benzyl-3-oxo-Δ4–1,2,4-thiadiazoline 5 with electrophilic nitriles, isothiocyanates, carbon disulfide and ketenes, yielding the products 6 and 7. In contrast, N,N'-ditolylcarbodiimide reacts with 5 to give the normal addition product 8 , which rearranges only partially to 9 in several solvents (chloroform, acetonitrile and dimethyl sulfoxide). The equilibrium position depends on the temperature, favoring 9 at higher temperatures. 相似文献
2.
Preparations for 2,3-diphenyl- and 2-benzyI-3-phenyl-Δ3-1,2,4-oxadiazolin-5-ones (3) and (4) and for 2,5-diphenyl-Δ4-1,2,4-oxadiazolin-3-one ( 7 ) are reported. 相似文献
3.
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
4.
Elena Bermejo Alfonso Castieiras Douglas X. West 《Journal of Molecular Structure》2003,650(1-3):93-97
Condensation of thiosemicarbazide or N(4)-ethylthiosemicarbazide with 1,2,8,9-tetraphenyl-3,7-diazanona-1,9-dione in the presence of copper(II) acetate in 96% ethanol leads to Δ6-5,6-diphenyl-5-methoxy-1,2,4-triazacyclohexene-3-thione, C16H15N3OS, or Δ6-4-methyl-5,6-diphenyl-5-ethoxy-1,2,4-triazacyclohexene-3-thione, C18H19N3OS. For C16H15N3OS the crystal data are monoclinic, P21/c, a=9.7780(7), b=8.5120(3), c=18.2210(13) Å, β=100.958(3)°, V=1488.89(16) Å3, and Z=4 in agreement with an earlier report. For C18H19N3OS the crystal data are orthorhombic, P212121, a=8.6940(3), b=12.9946(3), c=15.5139(5) Å, V=1752.68(9) Å3, and Z=4. 相似文献
5.
Nam Sook Cho Chan Soo Ra Do Young Ra Jin Soo Song Sung Kwon Kang 《Journal of heterocyclic chemistry》1996,33(6):1823-1828
2-Aroyl-5-aroylamino-1,2,4-thiadiazolin-3-ones 2 have been synthesized through aroylation of 5-amino-2H-1,2,4-thiadiazolin-3-one ( 1 ) as an analog of cytosine. The aroylation was carried out with a substituted aroyl chloride in pyridine at 56–58°. It has been established that the intermediates of the reactions are 2-aroyl-5-amino-1,2,4-thiadiazolin-3-ones 3 on the basis of the spectral data, additional experimental information and ab initio molecular orbital calculations. 相似文献
6.
Nam Sook Cho Chan Soo Ra Do Young Ra Jin Soo Song Sung Kwon Kang 《Journal of heterocyclic chemistry》1996,33(4):1201-1206
2-Aroyl-5-aroylamino-1,2,4-thiadiazolin-3-ones ( 2 ) have been synthesized through aroylation of 5-arruno-2H-1,2,4-thiadiazolin-3-one ( 1 ) as an analog of cytosine. The aroylation was carried out with a substituted aroyl chloride in pyridine at 56~58°C. It has been established that the intermediates of the reactions are 2-aroyl-5-amino-1,2,4-thiadiazolin-3-ones ( 3 ) on the basis of the spectral data, additional experimental information and ab initio molecular orbital calculations. 相似文献
7.
Gerrit L'Abb Ernestine Albrecht Suzanne Toppet 《Journal of heterocyclic chemistry》1992,29(5):1317-1319
The reactions of 2-alkyl-3-phenyl-Δ3-1,2,4-thiadiazolin-5-imines 5a,b with trichloroacetonitrile at room temperature yield rearranged products, which are shown by 1 H and 13C nmr spectroscopy to exist in two tautomeric structures 6 and 7 . 相似文献
8.
Chiara B. Vicentini Maurizio Manfrini Augusto C. Veronese Mario Guarneri 《Journal of heterocyclic chemistry》1998,35(1):29-32
Condensation of pyrazolyl isothiocyanates 2 with N-substituted hydrazines provided the 2-methyl/phenyl-4-(pyrazol-5-yl)thiosemicarbazides 3 . Cyclization of 3 with formic acid-acetic anhydride or with triethyl orthoacetate-acetic anhydride provided 4-(pyrazol-5-yl)-l,2,4-triazole-3-thiones 4a-f and 5-methyl-4-(pyrazol-5-yl)-1,2,4-triazole-3-thiones 4g-I respectively. 相似文献
9.
By reaction of arylhydrazones of benzoyl chloride with 4-aminomethylthiazole in the presence of triethylamine, the corresponding amidrazones were obtained, which upon oxidation gave 5-(thiazol-4-yl)-1,2,4-triazoles with fungicidal and bactericidal activity.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2111–2112, September, 1991. 相似文献
10.
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
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12.
Do Young Ra Nam Sook Cho Jung Hyun Moon Sung Kwon Kang 《Journal of heterocyclic chemistry》1998,35(6):1435-1439
5-Amino-2-acyl-1,2,4-thiadiazolin-3-ones 2–1 can be synthesized from 5-amino-2H-1,2,4-thiadiazolin-3-one ( 1–1 ) via a selective acylation with an acid anhydride in pyridine. The 1H nmr spectral characteristics of 5-amino-2-acyl-1,2,4-thiadiazolin-3-ones 2–1 is in particular, compared with 5-amino-2H-1,2,4-thiadiazolin-3-one ( 1–1 ) and 5-amino-2-alkyl-1,2,4-thiadiazolin-3-ones 1–2, 1–3 . The 5-amino group of 2–1 appeared as two peaks in its 1H nmr spectrum, which merged to a single peak at a higher temperature, while those of compound 1–1, 1–2 and 1–3 appear only as a single peak. The restricted rotation of the C(5)-N(5) (at amino) bond of 5-amino-2-acetyl-1,2,4-thiadiazolin-3-one (2a-1) is about 14.5 Kcal/mol. 相似文献
13.
T. V. Shokol V. A. Turov A. V. Turov N. V. Krivokhizha V. V. Semenyuchenko V. P. Khilya 《Chemistry of Heterocyclic Compounds》2005,41(11):1411-1418
The condensation of 4-phenyl-1,2,4-triazol-3-ylacetonitrile with 2-methyl-, 4-ethylresorcinol, and with pyrogallol gave α-(4-phenyl-1,2,4-triazol-3-yl)-2,4-dihydroxyacetophenones.
Upon treatment with acid anhydrides and chlorides and subsequent hydrolysis these form 7-hydroxy-3-(4-phenyl)-1,2,4-triazol-3-yl)chromones
with different substituents in both the benzene and the pyrone rings.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1676–1684, November, 2005. 相似文献
14.
Godovikova T. I. Vorontsova S. K. Konyushkin L. D. Firgang S. I. Rakitin O. A. 《Russian Chemical Bulletin》2010,59(2):483-485
A number of 3-methyl-4-(5-R-1H-1,2,4-triazol-3-yl)-1,2,5-oxadiazoles were obtained in high yields by thermal dehydration of acylated 4-methyl-1,2,5-oxadiazole-3-carboxamide
hydrazones. 相似文献
15.
《中国化学快报》1997,(3)
2-5-Disubstituted-1,3,4-oxadiazoIesand3,4-disubstituted-l,2.4-triazoleshavebeenreportedtopossessanhb8cterial'-',antiinflamatory';activity,andtobepIantgrowthpromoters"'.lnearlierreports'-',wedescribedthereactionof2-methylsulphon}!l-5-phenyl-l-3,4-oxadiazolewithavarietyofnucleophilicreagents,suchas,amine,azide.hy'drazine-andaryloxy.Inordertoscreennewcompoundsforphysiologicalactivity-wewouldliketodescribeanovelsynthesisofl2new(3-benZyl-4-aroyl-l,2,4-triazoIetrimethoxylphenyl)-1'3,4-oxadiaz(2)byn… 相似文献
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18.
Krinochkin A. P. Guda M. R. Kopchuk D. S. Shtaitz Ya. K. Starnovskaya E. S. Savchuk M. I. Rybakova S. S. Zyryanov G. V. Chupakhin O. N. 《Russian Journal of Organic Chemistry》2021,57(4):675-677
Russian Journal of Organic Chemistry - Methyl 3-(3,6-diaryl-1,2,4-triazin-5-ylamino)thiophen-2-carboxylates were synthesized in 70–75% yield by solvent-free reaction of methyl... 相似文献
19.
N-Methylimines of 3-aryl-1-phenylpyrazole-4-carbaldehyde react with ethyl 2-aryl-hydrazino-2-chloroacetate with the formation of ethyl 1-aryl-5-(pyrazole-4-yl)-4,5-dihydro-1H-1,2,4-triazolecarboxylates. Analogous reactions of pyrazol-4-carbaldehyde N-(2-hydroxy)ethylimines results in derivatives of 3-(pyrazol-4-yl)-1,2,4-triazolo[3,4-c][1,4]-oxazines. 相似文献
20.
A series of 3-(3-alkyl-5-thioxo-1H-4,5-dihydro-1,2,4-triazol-4-yl)aminocarbonylchromones has been prepared by oxidation of 3-formylchromone with Jones' reagent followed by reaction with 3-alkyl-4-amino-4,5-dihydro-1,2,4-triazole-5(1H)-thione in the presence of POCl3. The structures of the compounds were confirmed by IR, LC-MS, and 1H NMR spectra and elemental analyses. 相似文献