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1.
Ahmad M. Farag Abdelgawad A. Fahmi Abdou O. Abdelhamid Ahmad S. Shawali Mohamed S. Algharib 《Journal of heterocyclic chemistry》1987,24(5):1341-1344
The reaction of diazotized 3-phenyl-5-aminopyrazole with phenacyl thiocyanate 1a and phenacyl selenocyanate 1b afforded directly 2-imino-3-(3-phenyl-5-pyrazolyl)-5-benzoyl-2,3-dihydro-1,3,4-thiadiazole monohydrate 9a and 2-imino-3-(3-phenyl-5-pyrazolyl)-5-benzoyl-2,3-dihydro-1,3,4-selenadiazole monohydrate 9b , respectively. The products 9a and 9b were also obtained from the reaction of C-benzoyl-N-(3-phenyl-5-pyrazolyl)formohydrazidoyl bromide 10 with potassium thiocyanate and potassium selenocyanate, respectively. Acetylation, benzoylation, and nitrosation of 9 afforded the corresponding diacetyl, dibenzoyl, and nitroso derivatives 11-13 , respectively. Cyclization of C-benzoyl-N-(3-phenyl-5-pyrazolyl)-nitrilimine 6 was shown to give the pyrazolo [5,1-d]triazole 8 and not the pyrazolo[5,1-c]-as-triazine derivative 7 , as previously reported. 相似文献
2.
Three new alternative synthetic strategies based on reactions of hydrazonoyl halides 3 with 2-methylthiouracil 2 and treatment of either 2-pyrimidinyl thiohydrazonates 8 or the diazonium coupling products of active (pyrimidin-2-ylthio)methylene compounds 12 with sodium ethoxide in ethanol are described for the title compounds. The mechanisms and regiochemistry of the studied reactions are discussed. 相似文献
3.
Ahmad S. Shawali Magda A. Abdallah Mosselhi A. N. Mosselhi Mahmoud S. Elewa 《Journal of heterocyclic chemistry》2007,44(2):285-288
Reactions of 4‐arylhydrazono‐2‐methylthio‐imidazolin‐5(1H)‐one 3 with various hydrazonoyl halides 1 proved to be site‐selective and yielded the respective imidazo[2,1‐c][1,2,4]triazole derivatives 8 . The structure of the latter was elucidated by X‐ray analysis and the mechanism of the studied reactions was discussed. 相似文献
4.
Kinetics and Mechanism of Dehydrochlorination of 3‐Chloro‐1,5‐diarylformazans and Their Mass Spectra
In aqueous dioxane containing triethylamine the title 3‐chloroformazans 1 are converted into the corresponding 1,4‐bis(arylazo)‐3,6‐diaryl‐1,2,4,5‐tetrazines 3 via head‐to‐tail dimerization of the intitially formed 1,3‐dipolar ions 2. The kinetics of triethylamine‐catalyzed dehydrochlorination of 1 in 70% dioxane at 27°C and ionic strength of 0.1 were studied. The rate data were linearly correlated with enhanced Hammett substituent constants σx? and an overall ρ value of 0.2 was determined for the variation of the N‐aryl substituent. These results were interpreted in terms of a two‐step mechanism. Also, the mechanisms of the unimolecular fragmentation of 1 and 3 in the mass spectrometer are discussed. 相似文献
5.
Bahgat E. Elanadouli Abdou O. Abdelhamid Ahmad S. Shawali 《Journal of heterocyclic chemistry》1984,21(4):1087-1091
The polarographic behaviour of a series of 2-amino-4-phenyl-5-arylazothiazoles has been investigated at a dropping mercury electrode. Each of the compounds studied exhibits one wave which was shown to correspond to the reductive cleavage of the azo linkage by a 4e irreversible step. On the basis of the polarographic data, it was concluded that the compounds exist only in one tautomeric form, namely the aminoazo structure 1 . The results of E1/2 — σX correlations and HMO calculations of bonding energies of the various possible tautomeric forms 1–3 indicate that the aminoazo form 1 is the most stable structure of the compounds examined. 相似文献
6.
Abdou O. Abdelhamid Hamdi M. Hassaneen Ikhlass M. Abbas Ahmad S. Shawali 《Tetrahedron》1982,38(10):1527-1530
Diazotized anathranilic acid and its methyl ester react with substituted α-thiocyanatoacetoacetanilides3a–c to give in both cases the corresponding thiadiazolo [2,3-b] quinazolines6a–c, respectively. A mechanism is proposed and it is substantiated by synthesis of6a from N-(2-car?yphenyl)-C-phenylcarbamoyl hydrazidoyl chloride8a or its N-(2-methoxycarbonylcarbonylphenyl) analogue8d. 相似文献
7.
Ahmad S. Shawali Abdou O. Abdelhamid Hamdi M. Hassaneen Abdelfattah Shetta 《Journal of heterocyclic chemistry》1982,19(1):73-75
Diazotized anthranilic acid and its methyl ester react with substituted phenacyl thiocyanates 3 to give in both cases the corresponding thiadiazolo[2,3-b]quinazolines 7a-e . A mechanism is proposed and it is substantiated by alternate synthesis of 7a from the hydrazidoyl chlorides 9a,b and potassium thiocyanate. 相似文献
8.
A series of para- and meta-substituted phenylazoformaldoximes have been prepared and their acidities determined spectrophotometrically at 25.0±0.1°C and μ of 0.10 in ethanol-water mixtures containing 1, 50 and 80 vol. % ethanol. The pKa. data obtained were linearly correlated with the Hammett substituent constant, σx. The variation with solvent of the reaction constant, ?, was linear function of the solvent activity function, Y_. The ? value for the series studied in 99 vol. % water has been compared with that reported for the ionization of α-benzaldoximes. The results show that the azo bond transmits electronic effects approximately 1.5 times better than the ethylenic bond. 相似文献
9.
Ahmad S. Shawali Nagwa M. S. Harb Khadiga O. Badahdah 《Journal of heterocyclic chemistry》1985,22(5):1397-1403
The spectra (1H nmr, ir and uv) of a series of 3-arylazo-4-hydroxycoumarins 1a-m indicate that such compounds exist predominantly in the keto hydrazone form 1A both in solid state and in solution. The acid dissociation constants of the series studied were determined spectrophotometrically in 80 vol% ethanol-water mixture at 27° and ionic strength of 0.1. The results of the correlations of these constants by Hammett and Yukawa-Tsuno equations exclude the presence of the hydroxyazo form 1B in equilibrium with 1A in agreement with the spectral data. Also, the HMO method has been used to study tautomerism in such compounds. The results are also in full agreement with both the spectral and linear free energy correlations, the hydrazone form 1A being the most stable. It is further shown that both the intermolecular and intramolecular hydrogen bonding favor the hydrazone tautomer. 相似文献
10.
Treatment of N-phenylsulfonylarenehydrazonoyl chlorides (II) with equivalent amounts of aroylhydrazines (III) in ethanol gave 3,5-diaryl-4-phenylsulfonylamino-1,2,4-triazoles (IV). Reaction of II with two equivalents of III in tetrahydrofuran gave 2,5-diaryl-1,3,4-oxadiazoles (V), in addition to IV. Addition of triethylamine to II or its mixture with III yielded only the tetrazenes (VIII). The possible pathways leading to IV-V and VIII are discussed. J. Chem. Soc., 14, 1089 (1977) 相似文献