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1.
Mamdouh Ahmed Mohamed Taha 《中国化学会会志》2005,52(1):137-140
Reaction of 6‐mercapto‐7H‐1,2,4‐triazolo[1,5‐d]tetrazole ( 1 ) wtih 1,2‐phenylenediamine afforded N‐{7H‐1,2,4‐triazolo[1,5‐d]tetrazol‐6‐yl}‐1,2‐phenylenediamine which was cyclized to benzimidazolyl‐1,2,4‐triazolo[1,5‐d]tetrazoles using various one‐carbon cyclizing agents. Also, the treatment of 1 with maleic anhydride or phthalic anhydride gave the corresponding thio derivatives followed by hydrazinolysis to afford the thio heterobicyclic systems. Former structures of the products have been established upon elemental and spectral analyses. 相似文献
2.
Adel Z. Nasr 《中国化学会会志》2005,52(3):519-524
Heterocyclization of bis(2‐oxo‐indol‐3‐ylidene)‐galactaric acid hydrazide ( 3 ) with a variety of one‐nitrogen cyclizing agents gave the corresponding 1,4‐bis{1,2,4‐triazino[5,6‐b]indol‐3‐yl}‐galacto‐tetritols 4–8 . Acetylation of the latter double headed acyclo C‐nucleosides with acetic anhydride in the presence of pyridine at ambient temperature resulted in N‐ and O‐acetylation to give the corresponding 1,2,3,4‐tetra‐O‐acetyl‐1,4‐bis{1,2,4‐triazino[5,6‐b]indol‐3‐yl}‐galacto‐tetritols 9–13 which were found to exist in centro‐symmetric zigzag conformations 20 . The assigned structures were corroborated by 1H, 13C NMR as well as mass spectra. 相似文献
3.
A series of new chiral (S)‐3‐ary1‐6‐pyrrolidin‐2‐yl‐[1,2,4]triazolo[3,4‐b]thiadiazole (II1‐5), (S)‐1‐(3‐aryl‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazol‐6‐yl)‐ethylamine (II6‐8) and (S)‐1,2‐bis(3‐aryl‐[1,2,4]triazolo‐[3,4‐b][1,3,4]thiadiazol‐6‐yl)‐ethylamine (II9‐11) were prepared by the condensation of 3‐aryl‐4‐amino‐5‐mercapto‐1,2,4‐triazoles with different L‐amino acids in the presence of phosphorus oxychloride and evaluated for their antibacterial activity. 相似文献
4.
《Magnetic resonance in chemistry : MRC》2002,40(8):529-532
The 1H{15N} NMR spectrum of 5,7‐diphenyl‐1,2,4‐triazolo[1,5‐a]‐pyrimidine ( 3 ) was measured by GHMQC, unambiguously assigned and compared with the spectra of 1,2,4‐triazolo[1,5‐a]pyrimidine ( 1 ) and 5,7‐dimethyl‐1,2,4‐triazolo[1,5‐a]pyrimidine ( 2 ). A series of Au(III) chloride complexes of general formula AuLCl3, where L = 1 , 2 , 3 , was synthesized and studied by 1HH{15N} GHMQC and 1H{13C} GHMBC. Low‐frequency shifts of 72–74 ppm (15N) and 5–6 ppm (13C) were observed upon complexation by Au(III) ions for the coordination site N‐3 and adjacent C‐2, C‐3a atoms, respectively. The 13C signals of C‐5, C‐6, C‐7 and the 1H resonances of H‐2, H‐6 were shifted to higher frequency. Comparison with analogous Pd(II), Pt(II) and Pt(IV) complexes revealed that in the case of Au(III) coordination the 15N shifts were relatively smaller, whereas those for 13C and 1H were larger. Copyright © 2002 John Wiley & Sons, Ltd. 相似文献
5.
Synthesis of {3‐[1‐(ethoxycarbonyl)‐[1,2,4]triazolo[4,3‐a]quinoxalin‐4‐yl]‐1‐phenyl‐1H‐pyrazol‐5‐yl}methyl ethyl oxalate ( 2 ), ethyl 4‐[5‐(acetoxymethyl)‐1‐phenyl‐1H‐pyrazol‐3‐yl]‐[1,2,4]triazolo[4,3‐a]quioxaline‐1‐carboxylate ( 4 ), [4‐halo‐1‐phenyl‐3‐(1‐phenyl‐[1,2,4]triazolo[4,3‐a]quioxalin‐4‐yl)‐1H‐pyrazol‐5‐yl]methyl acetate ( 11 ), {4‐halo‐3‐[1‐methyl‐[1,2,4]triazolo[4,3‐a]quinoxalin‐4‐yl]‐1‐phenyl‐1H‐pyraz‐ol‐5‐yl}methyl acetate ( 13 ), and [3‐([1,2,4]triazolo‐[4,3‐a]quinoxalin‐4‐yl)‐4‐halo‐1‐phenyl‐1H‐pyrazol‐5‐yl] methyl formate ( 15 ) was accomplished. The structural investigation of the new compounds is based on chemical and spectroscopic evidences. J. Heterocyclic Chem., (2011) 相似文献
6.
Microwave‐assisted Synthesis of 6‐{(5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)methyl}‐6H‐indolo[2,3‐b]quinoxalines
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Sreenivas Avula Jayaram Reddy Komsani Satish Koppireddi Rambabu Yadla 《Journal of heterocyclic chemistry》2015,52(6):1737-1742
An efficient and convenient synthesis of a new series of 2‐{(6H‐indolo[2,3‐b]quinoxalin‐6‐yl)methyl}‐5‐aryl‐1,3,4‐oxadiazoles from readily available 1,2‐diaminobenzene and isatins under microwave irradiation conditions was disclosed. The 6‐{(5‐aryl‐1,3,4‐oxadiazol‐2‐yl)methyl}‐6H‐indolo[2,3‐b]quinoxalines were also prepared by the thermal cyclo‐condensation reaction of 2‐(6H‐indolo[2,3‐b]quinoxalin‐6‐yl)acetohydrazides with carboxylic acids in refluxing POCl3. The microwave‐assisted synthesis was rapid and resulted in higher yield of the products at lower operating temperature with reduced waste generation in comparison with the thermal reaction protocol. 相似文献
7.
Carlo Mustazza Maria Rosaria Del Giudice Anna Borioni Franco Gatta 《Journal of heterocyclic chemistry》2001,38(5):1119-1129
This paper describes the preparation of some pyrazolo[1,5‐a]‐, 1,2,4‐triazolo[1,5‐a]‐ and imidazo[1,2‐a]‐pyrimidines substituted on the pyrimidine moiety by a 4‐[(N‐acetyl‐N‐ethyl)amino]phenyl group. A new synthesis of related benzo[h]pyrazolo[1,5‐a]‐, benzo[h]pyrazolo[5,1‐b]‐ and benzo[h]1,2,4‐triazolo[1,5‐a]‐quinazolines is also reported. 相似文献
8.
《Journal of heterocyclic chemistry》2017,54(4):2258-2265
The present study emphasizes on the dealklylation of 3‐aryl‐5‐alkyl‐2‐oxo‐Δ4‐1,3,4‐oxadiazoles when reacted with formamide resulting in the formation of 2‐aryl‐2H‐1,2,4‐triazol‐3(4H )‐ones as major product. Subsequent reactions of 2‐aryl‐2H‐1,2,4‐triazol‐3(4H )‐one gave triazolo[3,4‐b ][1,3,4]thiadiazoles and triazolo[3,4‐b ][1,3,4]thiadiazines derivatives incorporated with 1,2,4‐triazol‐3‐one. 相似文献
9.
New CuII and CdII Metal‐organic Coordination Polymers with 1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazole Ligands: Syntheses,Structures and Luminescent Properties
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Three new complexes {[Cu( L1 )2(NO3)2]?H2O}oo ( 1 ), {[Cu4( L2 )2(OAc)8]‐CH3CH2OH}oo ( 2 ) and [Cd2( L3 )3(NO3)4(H2O)2]oo ( 3 ) ( L1= 4‐phenyl‐7‐(pyridine‐3‐yl)‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazole, L2= 4‐(pyridine‐3‐yl)‐7‐phenyl‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazole, and L3= 4‐(pyridine‐4‐yl)‐7‐phenyl‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazole) have been synthesized and characterized by elemental analyses, IR spectra and single crystal X‐ray diffraction. The structural analyses reveal that complex 1 is a neutral 2‐D network structure with a 44 topology, 2 has a 1‐D neutral coordination chain with a [Cu2(CH3COO)4] dinuclear structural unit bridged by four acetate ions, and 3 is a neutral rhombohedral grid structure. All the complexes are air stable at room temperature. Furthermore, the fluorescent properties of complex 3 and corresponding ligand L3 have been investigated and discussed. 相似文献
10.
Jzsef Reiter Jzsef Barkczy Gyula Argay Alajos Klmn 《Journal of heterocyclic chemistry》2000,37(2):261-267
Type 6 meso‐ionic [1,2,4]triazolo[5,1‐c]thiadiazoles were synthesised by oxidation of the corresponding N‐methyl‐N'‐(substitutedbenzal)‐5‐amino‐3‐substituted‐1,2,4‐triazol‐1‐yl)thiohydrazide ( 3 ) type bases or their [1,2,4]triazolo[5,1‐d][1,2,3,6]tetrazepin‐5‐thion ( 4 ) type ring tautomers. Besides spectroscopical evidence a preparative proof of their structure was also provided. X‐ray diffraction analysis of 3‐methylthio‐6‐morpholino‐1,2,4‐triazolo[5,1‐c]thiadiazole ( 8 ) showed quite unusual bond lengths for the N1‐S and S‐C3 bonds of the thiadiazole ring proving the meso‐ionic character of these derivatives unequivocally. 相似文献
11.
A synthesis of bis(α‐bromo ketones) 5a‐c and 6b,c was accomplished by the reaction of bis(acetophenones) 3a‐c and 4b,c with N‐bromosuccinimide in the presence of p‐toluenesulfonic acid (p‐TsOH). Treatment of 5a‐c and 6b,c with each of 4‐amino‐3‐mercapto‐1,2,4‐triazoles 9a,b and 4‐amino‐6‐phenyl‐3‐mercapto‐1,2,4‐triazin‐5(4H)‐ones 13 in refluxing ethanol afforded the novel bis(s‐triazolo[3,4‐b][1,3,4]thiadiazines) 10a‐d and 11a‐c as well as bis(as‐triazino[3,4‐b][1,3,4]thiadiazines) 14a‐c and 15 , respectively, in good yields. Compounds 11b and 11c underwent NaBH4 reduction in methanol to give the target 1,ω‐bis{4‐(6,7‐dihydro‐3‐substituted‐5H‐1,2,4‐triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl)phenoxy}butanes 12a and 12b in 42 and 46% yields, respectively. 相似文献
12.
Victoria V. Lipson Nataliya V. Svetlichnaya Victoria V. Borodina Maria G. Shirobokova Sergey M. Desenko Vladimir I. Musatov Svetlana V. Shishkina Oleg V. Shishkin Roman I. Zubatyuk 《Journal of heterocyclic chemistry》2012,49(5):1019-1025
Formylation of 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidine 1a using Vilsmeier–Haack conditions yields 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidin‐6‐ylcarbaldehyde 3a . 5,7‐Diaryl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidines 1b , 1c in this reaction apart from formylation undergo recyclization into 5‐aryl‐1,2,4‐triazolo[1,5‐a]pyrimidin‐6‐ylmethane derivatives 4b , 4c , 5b , 5c , and 6 . The structure of the synthesized compounds was determined on the basis of NMR, IR, and MS spectroscopic data and confirmed by the X‐ray analysis of the 6‐(ethoxy‐phenyl‐methyl)‐5‐phenyl‐[1,2,4]triazolo[1,5‐a]pyrimidine 6 , 5‐phenyl‐6‐(1‐phenyl‐vinyl)‐[1,2,4]triazolo[1,5‐a]pyrimidine 11 , and 7‐phenyl‐6‐(1‐phenyl‐vinyl)‐[1,2,4]triazolo[4,3‐a]pyrimidine 12 . 相似文献
13.
《Journal of heterocyclic chemistry》2018,55(3):586-592
New heterocyclic compounds 1‐(3‐methyl‐9H‐dibenzo[b,f][1,2,4]triazolo[4,3‐d][1,4]diazepin‐6‐yl)ethanone 8a , 1‐(3‐methyldibenzo[b,f][1,2,4]triazolo[4,3‐d][1,4]oxazepin‐6‐yl)ethanone 8b , and 1‐(3‐methyldibenzo[b,f][1,2,4]triazolo[4,3‐d][1,4]thiazepin‐6‐yl)ethanone 8c are synthesized from benzodiazepinone, benzoxazepinone, and benzothiazepinone derivatives. These heterocyclic scaffolds have wide medicinal importance. Best results were obtained in antibacterial screening against Escherichia coli, Enterobacter cloacae, and Staphylococcus aureus and antifungal screening against Candida albicans and Fusarium oxysporum. 1,1‐Diphenyl‐2‐picrylhydrazyl radical scavenging activities of compounds 6c , 7c , and 8c were tested in doses 10, 20, 30, 40, and 50 μg/mL and were expressed as IC50 values and percent of inhibition with means ± standard deviation of three different concentrations of synthesized compounds. The assignment of the structures of synthesized compounds was made by thin‐layer chromatography, elemental analysis, IR, 1H‐NMR, 13C‐NMR, and liquid chromatography–mass spectrometry. 相似文献
14.
Majid M. Heravi Naser Montazeri Mohammad Rahimizadeh Mehdi Bakavoli Mitra Ghassemzadeh 《Journal of heterocyclic chemistry》2005,42(5):1021-1025
In an attempt to discover bicyclic compounds containing the 1,2,4‐triazine moiety, 1,2,4‐triazolo[1,5‐d]‐1,2,4‐triazine‐5‐thiones from one pot reaction of arylnitriles with 4‐amino‐1,2,4‐triazine‐3‐thione‐5‐one in the presence of potassium tert‐butoxide were synthesized. 相似文献
15.
Guo-Xia Jin Tian-Chao You Jian-Ping Ma 《Acta Crystallographica. Section C, Structural Chemistry》2019,75(12):1690-1697
The new asymmetrical organic ligand 2‐{4‐[(1H‐imidazol‐1‐yl)methyl]phenyl}‐5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazole ( L , C17H13N5O), containing pyridine and imidazole terminal groups, as well as potential oxdiazole coordination sites, was designed and synthesized. The coordination chemistry of L with soft AgI, CuI and CdII metal ions was investigated and three new coordination polymers (CPs), namely, catena‐poly[[silver(I)‐μ‐2‐{4‐[(1H‐imidazol‐1‐yl)methyl]phenyl}‐5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazole] hexafluoridophosphate], {[Ag( L )]PF6}n, catena‐poly[[copper(I)‐di‐μ‐iodido‐copper(I)‐bis(μ‐2‐{4‐[(1H‐imidazol‐1‐yl)methyl]phenyl}‐5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazole)] 1,4‐dioxane monosolvate], {[Cu2I2( L )2]·C4H8O2}n, and catena‐poly[[[dinitratocopper(II)]‐bis(μ‐2‐{4‐[(1H‐imidazol‐1‐yl)methyl]phenyl}‐5‐(pyridin‐4‐yl)‐1,3,4‐oxadiazole)]–methanol–water (1/1/0.65)], {[Cd( L )2(NO3)2]·2CH4O·0.65H2O}n, were obtained. The experimental results show that ligand L coordinates easily with linear AgI, tetrahedral CuI and octahedral CdII metal atoms to form one‐dimensional polymeric structures. The intermediate oxadiazole ring does not participate in the coordination interactions with the metal ions. In all three CPs, weak π–π interactions between the nearly coplanar pyridine, oxadiazole and benzene rings play an important role in the packing of the polymeric chains. 相似文献
16.
《Journal of heterocyclic chemistry》2018,55(6):1450-1478
Novel [1,2,4]triazole derivatives were synthesized via various synthetic pathways. Among which were different substituted [1,2,4]triazole analogues that were synthesized, in addition to various fused [1,2,4]triazolo[1,5‐a]pyrimidine derivatives, [1,2,4]triazolo[1,5‐a][1,3,5]triazines, and [1,2,4]triazolo[5,1‐c][1,2,4]triazines. Besides, benzo[h][1,2,4]triazolo[5,1‐b]quinazolines, [1,2,4]triazolo‐[5,1‐b]quinazoline, [1,2,4]triazolo[1,5‐a]quinazoline and [1,2,4]triazolo[5,1‐d][1,2,3,5]tetrazine derivatives were also synthesized. The newly synthesized compounds were evaluated for their in vitro anticancer activity against liver cancer HepG2 and breast cancer MCF7 cell lines compared with the reference drug doxorubicin. Compounds 4 , 7 , 15 , 17 , 28 , 34 , and 47 were found to exert promising anticancer activity against HepG2 cell line showing IC50 values ranging from 17.69 to 25.4 μM/L, while compounds 7 , 14a , 17 , 28 , and 34 showed significant activity against MCF7 cell line with IC50 values ranging from 17.69 to 27.09 μM/L. 相似文献
17.
《Journal of heterocyclic chemistry》2017,54(2):1355-1360
A series of novel 1,3,4‐thiadiazoles, 1,2,4‐triazoles, and 1,3,4‐oxadiazoles were synthesized by cyclization of substituted 1‐(2‐(2‐chlorophenyl)‐2‐(4‐(2,3‐dichlorophenyl)piperazin‐1‐yl)acetyl)thiosemicarbazide. The structures of all newly synthesized compounds were elucidated on the basis of spectral studies. Some of them were screened for their antibacterial activity. The compounds 6b , 6c , 8e , 9a , and 9b have shown moderate activity towards Bacillus Subtilis and Escherichia Coli . 相似文献
18.
A Facile Synthesis of Aryl‐Substituted Hydrazono‐Pyrazolyl[1,2,4]triazolo[3,4‐b][1,3,4][thiadiazol]‐coumarin Derivatives
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Some inimitable and therapeutic coumarin‐substituted fused[1,2,4]triazolo‐[3,4‐b][1,3,4]thiadizole derivatives were synthesized by the cyclocondensation reaction of 2‐oxo‐2H‐chromene‐3‐carboxylic acid ( 1 ) and 4‐amino‐5‐hydrazinyl‐4H‐[1,2,4]‐triazole‐3‐thiol ( 2 ) by using phosphorous oxychloride as a cyclizing agent. This cyclized intermediate 3‐(3‐hydrazino‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazol‐6‐yl)‐chromen‐2‐one ( 3 ) later condensation with various ethyl 2‐(2‐arylhydrazono)‐3‐oxobutanoates ( 4 ) in NaOAc/MeOH under reflux conditions afforded the corresponding new series of aryl‐substituted hydrazono‐pyrazolyl‐[1,2,4]triazolo[3,4‐b][1,3,4][thiadiazol]‐coumarin derivatives ( 5 ) in good to excellent yields. The structures of newly synthesized compounds were established on the basis of elemental analysis, IR, 1H NMR and mass spectroscopic studies. 相似文献
19.
An Efficient,Multicomponent Synthesis of Pyrazolyl Triazolo Thiadiazinyl Chromen ‐ 2 ‐ Ones
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One‐pot synthesis of 3‐(3‐(3,5‐dimethyl‐1H‐pyrazol‐1‐yl)‐7H‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazin‐6‐yl)‐2H‐chromen‐2‐ones was achieved via the multicomponent reaction of purpald, acetyl acetone, and different derivatives of 3‐(2‐bromo‐acetyl)‐2H‐chromen‐2‐one in absolute ethanol. All the synthesized compounds were characterized by analytical and spectral data. 相似文献
20.
Abdou O. Abdelhamid Shokry A. Shokry Sayed M. Tawfiek 《Journal of heterocyclic chemistry》2012,49(1):116-124
Naphtho[2,1‐b]furan‐2‐yl)(8‐phenylpyrazolo[5,1‐c][1,2,4]triazin‐3‐yl)methanone, ([1,2,4]triazolo[3,4‐c][1,2,4]triazin‐6‐yl)(naphtho[2,1‐b]furan‐2‐yl)methanone, benzo[4,5]imidazo[2,1‐c][1,2,4]triazin‐3‐yl‐naphtho[2,1‐b]furan‐2‐yl‐methanone, 5‐(naphtho[2,1‐b]furan‐2‐yl)pyrazolo[1,5‐a]pyrimidine, 7‐(naphtho[2,1‐b]furan‐2‐yl)‐[1,2,4]triazolo[4,3‐a]pyrimidine, 2‐naphtho[2,1‐b]furan‐2‐yl‐benzo[4,5]imidazo[1,2‐a]pyrimidine, pyridine, and pyrazole derivatives are synthesized from sodium salt of 5‐hydroxy‐1‐naphtho[2,1‐b]furan‐2‐ylpropenone and various reagents. The newly synthesized compounds were elucidated by elemental analysis, spectral data, chemical transformation, and alternative synthetic route whenever possible. J. Heterocyclic Chem., (2012). 相似文献