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1.
Kinfe K. Redda Hailemichael Melles Kode Nageswara Rao 《Journal of heterocyclic chemistry》1990,27(4):1041-1046
Alkyl substituted 2,4-dinitrophenylpyridinium chlorides 3 are formed by the nucleophilic substitution of 1-chloro-2,4-dinitrobenzene with alkyl pyridines. Reaction of pyridyl acid hydrazides or benzoyl hydrazides 4 with the pyridinium chlorides 3 furnish the isolable 2,4-dinitroanilino derivatives 5 which undergo hydrolysis when refluxed in water:p-dioxane mixture (1:4 v/v) to yield the pyridinium ylides 6 . Sodium borohydride reduction of 6 in absolute ethanol at 0° for 4 hours result the formation of the title compounds 7 in moderate to excellent yields. 相似文献
2.
K K Redda K N Rao A S Heiman F Y Onayemi J B Clark 《Chemical & pharmaceutical bulletin》1991,39(3):786-791
Nucleophilic attack of tert-butyl/phenylpyridines 3 on 1-chloro-2,4-dinitrobenzene 4 results in the formation of tert-butyl/phenyl substituted 2,4-dinitrophenylpyridinium chlorides 5. Benzoyl hydrazide and pyridyl acid hydrazides 6 were reacted with the pyridinium chlorides 5 furnishing the 2,4-dinitroanilino derivatives 7, which were subsequently hydrolyzed with water: p-dioxane to yield N-[pyridyl(phenyl)carbonylimino]-tert-butyl/phenylpyridinium ylides 8. The title compounds 9, N-[pyridyl(phenyl)carbonylamino]-tert-butyl/phenyl-1,2,3,6- tetrahydropyridines, were obtained by sodium borohydride reduction of the pyridinium ylides 8. The anti-inflammatory activities of compounds 9a-p were determined using the carrageenan-soaked sponge model of inflammation in Sprague Dawley rats. All compounds tested showed moderate to good anti-inflammatory effects compared to indomethacin. Compounds 9b, 9c and 9p were the most active analogs of the group in this model. 相似文献
3.
S. Yu. Ryabova L. M. Alekseeva N. A. Rastorgueva E. A. Lisitsa D. M. Papakhin V. A. Parshin V. G. Granik 《Russian Chemical Bulletin》2006,55(12):2278-2284
Reactions of 3-[(N-aryl-N-chloroacetyl)amino]-2-formylindoles with substituted anilines gave 1,4-diaryl-2-oxo-1,2,3,6-tetrahydro[1,4]diazepino[6,5-b]indol-4-ium chlorides and those with 4-aminopyridine yielded 4-amino-1-(1-aryl-2-oxo-2,5-dihydro-1H-pyrido[3,2-b]indol-3-yl)pyridinium chlorides. Reduction of 1,2,3,6-tetrahydrodiazepinoindol-4-ium chlorides afforded the corresponding
hexahydro derivatives. An alternative synthesis of 1-(4-nitrophenyl)-3-oxo-4-phenyl-1,2,3,4,5,6-hexahydro[1,4]diazepino[6,5-b]indole from 3-[N-(4-nitrophenyl)amino]-2-[(phenylimino)methyl]indole was developed. The method involves the following sequence of transformations:
reduction, chloroacetylation, and intramolecular alkylation.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2193–2199, December, 2006. 相似文献
4.
Kyoung Jin P. Yoon Bala Kode Lynneice Bowen Kinfe K. Redda 《Journal of heterocyclic chemistry》2001,38(1):69-76
Fourteen novel N‐(substituted phenylcarbonylamino)‐4‐ethyl‐1,2,3,6‐tetrahydropyridines 9 were synthesized in fair to good yields. 4‐Ethylpyridine 5 reacted with O‐mesitylenesulfonylhydroxylamine (O‐MSH) 4 to furnish N‐amino‐4‐ethylpyridinium mesitylenesulfonate 6 . The reaction of 6 with substituted acid chlorides 7 gave the stable crystalline pyridinium ylides 8a‐8n . A sodium borohydride reduction of 8 in absolute ethanol furnished the target compounds N‐(substituted phenylcarbonylamino)‐4‐ethyl‐1,2,3,6‐tetrahydropyridines 9a‐9n . 相似文献
5.
Condensation of chlorocarbonylsulfenyl chloride 1 with 1-(5-(1,1-dimethylethyl)-1,2-oxazol-3-yl)-3-methylurea 4a has been found to give isomeric 2,4-disubstituted-1,2,4-thiazolidine-3,5-diones 5 and 6 . Assignments are confirmed by the X-ray structure data of 6 . Sulfenylation with alkoxycarbonylsulfenyl chlorides 7 and trichloromethylsulfenyl chloride 10 of 4 occurs exclusively on N-1 rather than N-3 of the urea moiety. With the isomeric 1-[3-(1,1-dimethylethyl)-1,2-oxazol-5-yl]-3-methylurea 14 and ethoxycarbonylsulfenyl chloride 7b , C-sulfenylated derivatives 15 and 16 are formed in low yield. 相似文献
6.
Bakr F. Abdel-Wahab Hatem A. Abdel-Aziz Essam M. Ahmed 《Monatshefte für Chemie / Chemical Monthly》2009,140(6):601-605
Abstract Potassium hydrazinecarbodithioate were prepared by treatment of acid hydrazides with carbon disulfide in the presence of potassium
hydroxide. Reaction of this potassium salt with hydrazine hydrate, phenacyl bromide, or hydrazonoyl chlorides afforded 1,2,4-triazole,
1,3-thiazole, and 1,3,4-thiadiazoles. Reaction of 1,2,4-triazole with phenacyl bromide or hydrazonoyl chlorides afforded the
corresponding 1,2,4-triazolo[3,4-b][1, 3, 4]-thiadiazines. All these new compounds were screened for antibacterial and antifungal activity. Some had promising
activity.
Graphical abstract
相似文献
7.
Dong H. Kim 《Journal of heterocyclic chemistry》1986,23(5):1471-1474
The treatment of 4-(2-aminophenyl)-1,4-dihydro-2,6-dimethyl-3,5-pyridinecarboxylic acid diethyl ester (III) with refluxing toluene or pyridine afforded 1,2,3,6-tetrahydro-2,4-dimethyl-2,6-methano-1,3-benzodiazocine-5,11-dicarboxylic acid diethyl ester (IV) as the major product. In addition, the following minor products were isolated: 2-methyl-3-quinolinecarboxylic acid ethyl ester (V), 3-(2-aminophenyl)-5-methyl-6-azabicyclo[3,3,1]-hept-1-ene-2,4-dicarboxylic acid diethyl ester (VI), and 5,6-dihydro-2,4-dimethyl-5-oxobenzo[c][2,7]naphthyridine-1-carboxylic acid ethyl ester (VII). In contrast, acidic conditions caused the conversion of III into V in a 95% yield. The formation of the latter appears to involve IV as an intermediate, since IV degraded rapidly in acid to give V in a quantitative yield. 相似文献
8.
Britsun V. N. Esipenko A. N. Kudryavtsev A. A. Lozinskii M. O. 《Russian Journal of Organic Chemistry》2004,40(2):232-238
A new procedure for preparation of 2-R-5-aryl-5,6-dihydro-7H-[1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones by condensation of 5-R-1,2,4-triazole-3-thiones with 3-arylacryloyl chlorides was developed. The thiazine ring of the [1,2,4]triazolo[5,1-b][1,3]thiazin-7-ones is easily cleaved by treating with ammonia and hydrazine affording amides and hydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-ylsulfanyl)propanoic acids. The latter react with isothiocyanates furnishing carbamoyl thiohydrazides of 3-aryl-3-(1H-1,2,4-triazol-5-ylsulfanyl)propanoic acids that in alkaline media undergo cyclization into 4-aryl-5-[2-(4H-1,2,4-triazol-5-ylsulfanyl)-2-phenylethyl]-2,4-dihydro-3H-1,2,4-triazole-5-thiones. 相似文献
9.
John P. Chupp 《Journal of heterocyclic chemistry》1971,8(4):565-570
Alkyl (1-cyclohexen-1-yl)carbamoyl chlorides ( 1 ) react with thiocyanate ion to form enecarbamoyl thiocyanates ( 2 ). In pyridine solution 2 readily isomerizes to the isothiocyanate 4 , which however is not isolated, but immediately transformed in good yields to tetrahydro-4-thio-2,4(lH,3H)quinazolinediones ( 3 ). Various transformations of 3 , including conversion to tetra-hydro-2,4(2H,4H)quinazolinedione ( 5 ), dithione ( 6 ), alkylation products ( 8 and 9 ), sodium salts 11 and Raney nickel degradation to 4,4a,5,6,7,8,8a-octahydro-l-methyl-2(1H)quinazolinone ( 7 ), were carried out to investigate their chemistry and substantiate structural assignments. 相似文献
10.
Yasumitsu Tamura Yasuyoshi Miki Toshiko Honda Masazumi Ikeda 《Journal of heterocyclic chemistry》1972,9(4):865-868
Ring opening of N-(2,4-dinitrophenyl)pyridinium chlorides with hydrazine followed by recyclization resulted in the formation of N-aminopyridinium salts. The scope of this reaction sequence was determined and several new 3-substituted N-aminopyridinium salts were prepared. 相似文献
11.
Bakr F. Abdel-Wahab Hatem A. Abdel-Aziz Essam M. Ahmed 《Monatshefte für Chemie / Chemical Monthly》2009,20(7):601-605
Abstract
Potassium hydrazinecarbodithioate were prepared by treatment of acid hydrazides with carbon disulfide in the presence of potassium hydroxide. Reaction of this potassium salt with hydrazine hydrate, phenacyl bromide, or hydrazonoyl chlorides afforded 1,2,4-triazole, 1,3-thiazole, and 1,3,4-thiadiazoles. Reaction of 1,2,4-triazole with phenacyl bromide or hydrazonoyl chlorides afforded the corresponding 1,2,4-triazolo[3,4-b][1, 3, 4]-thiadiazines. All these new compounds were screened for antibacterial and antifungal activity. Some had promising activity. 相似文献12.
Peter Xaver Iten Hana Mrki-Danzig Herbert Koch Conrad Hans Eugster 《Helvetica chimica acta》1984,67(2):550-569
Isolation and Structure Elucidation of Pteridines (Lumazines) from Russula sp. (Basidiomycetes) Extensive chromatogaphic separations and spectroscopic investigations have led to the isolation and identification of several water-soluble pteridines from Russula sp., the so-called russupteridines, namely: 1-(5-amino-2-6-dioxo-1,2,3,6-tetrahydeopyrimidin-4-yl)amino-1-deoxy-D -ribitol ( 1 ; a pro-lumazine; first identification in a basidiomycete(; l-deoxy-l-(6-methyl-2-4,7-trioxo-1,2,3,4,7,8-hexahydro-pteridin-8-yl)-D -ribitol ( 3 ) and l-deoxy-1-(2,4,7-trioxo-1,2,3,4,7,8-hexahydeopteridin-8-yl)-D -ribitol ( 4 ); both compounds found for the first time in higher fungi; they belong to the components with the strongest violet-blue fluorescence in Russula sp.; riboflavine ( 6 ; now recognized as an important yellow colorant in a great many of Russula sp.); russupteridine-yellow I (= l-(6-amino-7-(N-fromylimino)-2,4-dioxo-1,2,3,4,7,8-hexahydropteridin-8-yl)-1-deoxy-D -ribitol; 5 ; a component with very strong fluorescence; the first derivative of the novel 6,7-diamino-lamazine); russupteridine-yellow IV (= l-deoxy-1-)(2,6,8-trioxo-2,4,5,6,7,8-hexahydro-1H-imidazolo[4,5-g]pteridin-4-yl)-D -ribitol (7)). Two further yellow russupteridines (yellow II and Yellow V) with very strong fluorescence have been isolated and characterized. 相似文献
13.
Bis(1,3,4‐oxadiazoles) 4 , 5 and bis(1,2,4‐triazoles) 6a , 6b have been prepared from 3,6‐dioxa‐1,8‐octanedithiol 1 through a multistep reaction sequence. Compound 4 reacted with the appropriate alkyl halide in the presence of potassium carbonate in refluxing acetone to give the corresponding bis(S‐alkylated‐1,3,4‐oxadiazoles) 7a , 7b . The title compound 8 was prepared by condensing 4 with benzoyl bromide in the presence of triethylamine. Further, 6,9‐dioxa‐3,12‐dithiotetradecanedihydrazide 3 was converted to bis{N′‐(phenylaminocarbonyl) hydrazides} and bis{N′‐(phenylaminocarbonothioyl)hydrazides} 9a , 9b using phenylisocyanate and phenylthioisocyanate, respectively, which underwent cyclization in alkaline medium to produce 6,9‐dioxa‐3,12‐dithiotetradecane bis(4‐phenyl‐2,4‐dihydro‐3H‐1,2,4‐triazol‐3‐one) and their 3‐thio analogs 10a , 10b . The new compounds 4 , 5 , 6 , 7 , 8 , 9 , 10 were characterized by their IR, 1H‐NMR, 13C‐NMR, MS, and elemental analyses. 相似文献
14.
2(3H)‐Furanones 1 were utilized for the construction of pyrrolinotriazine and oxazolopyrimidine derivatives 4 and 9 . Thus, 1 reacted with glycine in ethanol at 70°C to give the acids 2 , which were cyclized into the pyrrolin‐5‐one derivatives 3 by the action of HCl/AcOH. The later compounds 3 were also obtained by refluxing the furanones 1 with glycine in glacial AcOH for 10 h. The carboxy functionality in 3 was used for the construction of a triazinone ring by treatment with thionyl chloride followed by refluxing the acid chloride with hydrazine in ethanol. The conversion of the furanones 1 into the oxazolopyrimidine derivatives 9 involved the following steps: (i) ring opening of the lactone ring with hydrazine hydrate to give the acid hydrazides 5 , (ii) conversion of the hydrazides 5 into the corresponding acyl azides 6 by action of NaNO2/AcOH, (iv) base‐catalyzed decomposition of the azides in the presence of glycine, (v) ring closure of the urea derivatives 7 into the pyrimidine derivatives 8 , and finally (vi) condensing 8 with benzaldehyde in the presence of NaOAc/AcOH mixture. 相似文献
15.
Abstract Cardo polysulfonates (PSBCB and PSBCT) of 1,1′-bis(4-hydroxy phenyl)cyclohexane with benzene-1,3 and toluene-2,4-disulfonyl chlorides have been synthesized by interfacial polycondensation of 1,1′-bis(4-hydroxy phenyl)cyclohexane (0.005 mol) with benzene-1,3/toluene-2,4-disulfonyl chlorides (0.005 mol) using water-chloroform (4:1, v/v) as interphase, alkali (0.015 mol) as acid acceptor, and cetyl trimethyl ammonium bromide (0.125 g) as emulsifier at 0°C for 3 hours. The structures of the polymers were supported by IR and NMR spectral data. The PSBCT was fractionated into several fractions by using 1,2-dichloroethane as solvent and n-butanol as precipitant. The fractions were characterized by GPC and viscometry in different solvents at four different temperatures. Viscosity studies showed that the PSBCT is flexible in solutions and has a specific solvent effect. PSBCB and PSBCT have good biological activity against E. coli and S. citrus organisms, and they possess excellent hydrolytic stability toward acids and alkalis. 相似文献
16.
Reactions of 5,7-diaryl-1,3-dimethyl-2,4-dioxo-1H,3H-pyrano[4,3-d]pyrimidinium bromides with phenylhydrazines and aromatic acid hydrazides have been studied. The reaction of the salts indicated
with phenylhydrazine at ∼20 °C results in the pyrylium ring opening, whereas elevated temperature leads to recyclization products,
i.e., 1,3-dimethylpyrido[4,3-d]pyrimidine-2,4(1H,3H)-diones. The reactions of the starting bromides with m-carboxyphenylhydrazine and aromatic acid hydrazides lead to 6-(R-amino)-1,3-dimethyl-2,4-dioxo-1H,3H-pyrido[4,3-d]-pyrimidinium salts. 相似文献
17.
Isao Yamaguchi Hideo Higashi Shunsuke Kimura Moriyuki Sato 《Helvetica chimica acta》2010,93(5):819-828
Diacetylenes (DAs) having a dipolar D‐π‐A structure (D=donor: amino group; π=π‐conjugation core; A=acceptor: pyridinium (Py) and bipyridinium (BPy) groups), i.e., 4 (APBPyDA) and 5 (APPyPyDA), or an A‐π‐A structure, i.e., 7 (DBPyDA) and 8 (PyDA(Cl)), were obtained by 1 : 1 and 1 : 2 reactions of 4,4′‐(buta‐1,3‐diyne‐1,4‐diyl)bis[benzenamine] (APDA; 3 ) with 1‐(2,4‐dinitrophenyl)‐1′‐hexyl‐4,4′‐bipyridinium bromide chloride (1 : 1 : 1) ( 1 ), 1‐(2,4‐dinitrophenyl)‐4‐(pyridin‐4‐yl)pyridinium chloride ( 2 ), or 1‐(2,4‐dinitrophenyl)pyridinium chloride ( 6 ) (Schemes 1 and 2). The anion‐exchange reactions of 8 with NaI and Li(TCNQ) (TCNQ?=2,2′‐(cyclohexa‐2,5‐diene‐1,4‐diylidene)bis[propanedinitrile] radical ion (1?)) yielded the corresponding I? and TCNQ? salts 9 (PyDA(I)) and 10 (PyDA(TCNQ)). Compounds 10 and 4 exhibited a UV/VIS absorption due to a charge transfer between the TCNQ? and the pyridinium groups and a strong solute–solvent interaction of a dipolar solute molecule in the polar environment, respectively. Compounds 8 – 10 exhibited photoluminescence in solution, whereas 4 and 7 did not because of the presence of the 4,4′‐bipyridinium quenching groups. Differential‐scanning‐calorimetry (DSC) measurements suggested that the DAs obtained in this study can be converted into poly(diacetylenes) by thermal polymerization. 相似文献
18.
The reaction of 2-amino-4-methyl-6-(2-pyridyl)-7,8-dihydroindazolo[4,5-d]thiazole, obtained by treating 3-methyl-4-oxo-1-(2-pyridyl)-4,5,6,7-tetrahydroindazole with pyridinium bromide perbromide and then with thiourea, and 2-amino-4-methyl-6-phenyl-7,8-dihydroindazolo[4,5-d]thiazole with 4-bromo-, 4-fluoro-, 4-dimethylamino-, 4-methoxy-, 3,4-dimethoxy-, and 3,4-methylenedioxybenzaldehydes, furfural, pyridinecarbaldehyde, and thiophenecarbaldehyde gave the corresponding Schiff bases. The products of the condensation of these aminothiazoles with cinnamaldehyde, 1-(2-pyridyl)- and 4-chloro-1-(2,4-difluorophenyl)-5-formyl-3-methyl-6,7-dihydroindazoles, 2-formyl-dimedone, and 2-formyl-1,3-indanedione were also obtained. 相似文献
19.
John M. Kokosa Ih Chu Ludwig Bauer Richard S. Egan 《Journal of heterocyclic chemistry》1976,13(4):861-868
The reaction of 4-t-butylpyridine 1-oxide (1) with t-butyl or 1-adamantyl mercaptan in acetic anhydride yielded the expected 2- and 3-alkylthio-4-t-butylpyridines and 1-acetyl-2,6-bis-(alkylthio)-3-acetoxy-4-t-butyl- and the unexpected 1-acetyl-2-acetoxy-3,6-bis(alkylthio-4-t-butyl-1,2,3,6-tetrahydropyridines. The addition of t-butyl mercaptan to a solution of 1 in acetic anhydride containing triethylamine produced the expected 1-acetyl-2-t-dmtylthio-3-acetoxy-4-t-butyl-6-hydroxy-1,2,3,4-tetrahydropyridine ( 6a ) and the unexpected 1-acetyl-2,6-bis(hydroxy)-3-t-butylthio-4-t-butyl-1,2,3,6-tetrahydropyridine. Mild alkaline hydrolysis of 6a yielded predominantly 2-[(acetamido) (t-butylthio)methyl]-3-t-butyl-5-hydroxy-2,5-dihydrofuran. The latter was converted by very mild acidic reagents to the corresponding furan and with 2,4-dinitrophenylhydrazine and sulfuric acid furnished 3-t-butylfurfural 2,4-dinitrophenyl-hydrazone. 相似文献
20.
R. S. Baltrushis Z. -I. G. Beresnevichyus I. M. Vizgaitis 《Chemistry of Heterocyclic Compounds》1981,17(8):816-820
The reaction of aniline with methacrylic and crotonic acids gave N-phenyl-- or -methyl--alanines, which were converted to the corresponding 1-phenyl-5(6)-methyl- and 1-phenyl-2-thioxo-5(6)-methyldihydrouracils by the action of urea or thiocyanates in an acidic medium. The dihydrouracils were converted to ureido acids by the action of alkalis and to N-phenyl--alanine hydrazides by the action of hydrazine. 1-Phenyl-2-thioxo-5-methylhexahydropyrimidine was isolated in the reduction of the thioxodihydrouracil. The dihydro- and thioxodihydrouracils react with phosphorus pentasulfide to give 4-thioxo- and 2,4-dithioxodihydrouracils. 1-Phenyl-5(6)-methyldihydrocytosines were obtained from the 4-thioxodihydrouracils. The thioxodihydrouracils were subjected to bromination; 1-(4-bromophenyl)-5(6)-methyldihydrouracils were obtained from 1-phenyl-5(6)-methyldihydrouracils, and 1-phenyl-2-thioxo-5-bromo-5-methyldihydrouracil, which was converted to a uracil by dehydrobromination, was obtained from 1-phenyl-2-thioxo-5-methyldihydrouracil. 1-Phenyl-2-thioxo-5-methyluracil was also obtained by dehydrogenation of 1-phenyl-2-thioxo-5-methyldihydrouracil with sulfur.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1097–1101, August, 1981. 相似文献