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1.
Victoria V. Lipson Irina V. Ignatenko Sergey M. Desenko Svetlana V. Shishkina Oleg V. Shishkin Sergey A. Komykhov Natalya V. Logvinenko Valery D. Orlov Herbert Meier 《Journal of heterocyclic chemistry》2003,40(6):1081-1086
The reaction of 5,7‐diphenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidine ( 1 ) with α,β‐unsaturated carbonyl compounds 2a‐f led to the formation of the alkylated heterocycles 3a‐f (Figure 1). However, the reaction of 5‐methyl‐7‐phenyl‐4,7‐dihydro‐1,2,4‐triazolo[1,5‐a]pyrimidine ( 5 ) with 2a‐c yielded under the same conditions the triazolo[5,1‐b]quinazolines 6a‐c (Figure 3). In this case, the alkylation is followed by a cyclocondensation. The structure elucidation of the products is based on ir, ms, 1H and 13C nmr measurements and on an X‐ray diffraction study. 相似文献
2.
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
3.
Hatem A. Abdel‐Aziz Nehal A. Hamdy Issa M. I. Fakhr Ahmad M. Farag 《Journal of heterocyclic chemistry》2008,45(4):1033-1037
4.
Green One‐Pot Solvent‐Free Synthesis of Pyrazolo[1,5‐a]pyrimidines,Azolo[3,4‐d]pyridiazines,and Thieno[2,3‐b]pyridines Containing Triazole Moiety
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Abdou O. Abdelhamid Tamer T. El‐Idreesy Nadia A. Abdelriheem Huda R. M. Dawoud 《Journal of heterocyclic chemistry》2016,53(3):710-718
Synthesis of pyrazolo[1,5‐a]pyrimidines, [1,2,4]triazolo[1,5‐a]pyrimidine, 8,10‐dimethyl‐2‐(5‐methyl‐1‐phenyl‐4,5‐dihydro‐1H‐1,2,3‐triazol‐4‐yl)pyrido[2′,3′:3,4]‐pyrazolo[1,5‐a]pyrimidine, benzo[4,5]imidazo[1,2‐a]pyrimidine via heterocyclic amines, and sodium 3‐hydroxy‐1‐(5‐methyl‐1‐phenyl‐1H‐1,2,3‐triazole‐4‐yl)prop‐2‐en‐1‐one were carried out. Also, synthesis of isoxazoles, and pyrazoles from sodium 3‐hydroxy‐1‐(5‐methyl‐1‐phenyl‐1H‐1,2,3‐triazole‐4‐yl)prop‐2‐en‐1‐one and hydroxymoyl chlorides and hydrazonoyl halides, respectively, were made. Analogously, (1,2,3‐triazol‐4‐yl)thieno[2,3‐b]pyridine derivatives were obtained from sodium 3‐hydroxy‐1‐(5‐methyl‐1‐phenyl‐1H‐1,2,3‐ triazole‐4‐yl)prop‐2‐en‐1‐one and cyanothioacetamide followed by its reacting with active methylene compounds. In addition to full characterization of all synthesized compounds, they were tested to evaluate their antimicrobial activities, and some compounds showed competitive activities to those of tetracycline, the typical antibacterial drug, and clotrimazole, the typical antifungal drug. 相似文献
5.
Synthesis of 2,5,7‐Triaryl‐4,7(6,7)‐dihydropyrazolo[1,5‐a]pyrimidine‐3‐carbonitriles by Reaction of 5(3)‐Amino‐3(5)‐aryl‐1H‐pyrazole‐4‐carbonitriles with Chalcones
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Maksim A. Kolosov Dmitriy A. Beloborodov Olesia G. Kulyk Valeriy D. Orlov 《Journal of heterocyclic chemistry》2014,51(Z1):E89-E92
The reaction of 5(3)‐amino‐3(5)‐aryl‐1H‐pyrazole‐4‐carbonitriles with 1,3‐diaryl‐2‐propen‐1‐ones (chalcones) in refluxing DMF leads to 2,5,7‐triaryl‐4,7(6,7)‐dihydropyrazolo[1,5‐a]pyrimidine‐3‐carbonitriles. In DMSO solution, the latter exist in equilibrium of two tautomeric 4,7‐dihydropyrazolo[1,5‐a]pyrimidines and 6,7‐dihydropyrazolo[1,5‐a]pyrimidines in various ratios, depending on the nature of aryl substituents in chalcone building blocks. 相似文献
6.
Regioselective Synthesis of Some New Pyrazolo[1,5‐a]pyrimidines,Pyrazolo[1,5‐a]quinazoline and Pyrimido[4′,5′:3,4]pyrazolo[1,5‐a] pyrimidines Containing Thiazole Moiety
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Samir Bondock Abd El‐Gaber Tarhoni Ahmed A. Fadda 《Journal of heterocyclic chemistry》2015,52(6):1792-1799
A regioselective synthesis of novel pyrazolo[1,5‐a]pyrimidines, pyrazolo[1,5‐a]quinazoline and pyrimido[4′,5′:3,4]pyrazolo[1,5‐a]pyrimidines incorporating a thiazole moiety was described via the reactions of the versatile, readily accessible 5‐amino‐3‐(phenylamino)‐N‐(4‐phenylthiazol‐2‐yl)‐1H‐pyrazole‐4‐carboxamide 3 with appropriate 1,3‐biselectrophilic reagents namely, β‐diketones, enaminones, and α,β‐unsaturated cyclic ketone. The newly synthesized compounds were elucidated by elemental analysis, spectral data, and alternative synthetic route whenever possible. 相似文献
7.
Antonino Lauria Patrizia Diana Paola Barraja Anna Maria Almerico Girolamo Cirrincione Gaetano Dattolo 《Journal of heterocyclic chemistry》2000,37(4):747-750
Derivatives of the new ring system pyrrolo[3,4‐e][1,2,3] triazolo[1,5‐a]pyrimidine 6 were prepared in high yields in one step by reaction of 3‐azidopyrrole 3 and substituted acetonitriles. Compound 6b rearranged, upon heating in dimethyl sulfoxide in the presence of water, to pyrrolo[3,4‐d][1,2,3]triazolo‐[1,5‐a]pyrimidine 7. 相似文献
8.
A series of novel 6‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]‐7‐phenylpyrazolo[1,5‐a]pyrimidines, 5‐phenyl‐6‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]imidazo[1,2‐a]pyrimidines, and 2‐phenyl‐3‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]pyrimido[1,2‐a]benzimidazoles have been synthesized in four steps starting with 2‐hydroxyacetophenone. The intermediate 3‐[(1,3,4‐thiadiazol‐2‐yl)sulfanyl]‐4H‐1‐benzopyran‐4‐ones reacted with pyrazol‐3‐amines, 5‐methylpyrazol‐3‐amine, and 1H‐imidazol‐2‐amine, 1H‐benzimidazol‐2‐amine via a cyclocondensation to give the title compounds in the presence of MeONa as base, respectively. The approach affords the target compounds in acceptable‐to‐good yields. The new compounds were characterized by their IR, NMR, and HR mass spectra. 相似文献
9.
Synthesis and Antifungal Activities of Some New 5,7‐Disubstituted[1,2,4]Triazolo[1,5‐a]Pyrimidin‐6‐one Derivatives
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Susanta Kumar Borthakur Sukanya Borthakur Debarshi Goswami Paran Boruah Pabitra Kumar Kalita 《Journal of heterocyclic chemistry》2016,53(6):2079-2083
Synthesis of a new series of [1,2,4]triazolo[1,5‐a]pyrimidin‐6‐one by [4 + 2]cycloaddition reaction of 3‐benzylidineamino[1,2,4]triazole with monophenyl ketene and diphenyl ketene generated in situ from phenylacetyl chloride and diphenylacetyl chloride in the presence of triethylamine is described. The newly synthesized compounds were also tested for antifungal activities against Rhizoctonia solani and Trichoderma sp. 相似文献
10.
Novel synthesis of (1H)‐pyridin‐2‐one, pyrazolo[1,5‐a]pyrimidine and isoxazole derivatives incorporating N‐methylphthalimide moiety are reported. Reaction of enaminone 2 with malononitrile affords 4. Condensation of 2 with cyanothioacetamide or benzoylacetonitrile affords compounds 6 and 7 respectively. Reaction of 2 with hydrazine hydrate afford 2,3‐dihydrophthalazine‐1,4‐dione ( 10 ). Condensation of 2 with hydroxylamine and 3‐aminopyrazole derivatives affords compounds 12 and 15a,b respectively. Antimicrobial and antifungal activity were determined for representative compounds and most of them showed moderate activity as antimicrobial agents, while compounds 2 and 7 show strong activity against Aspergillus niger. The structure of the newly synthesized compounds was elucidated by elemental analyses and 1H nmr spectra and some cases by 13C nmr investigation. 相似文献
11.
《Journal of heterocyclic chemistry》2018,55(7):1804-1808
A diversity of new 7 ‐substituted[1,2,4]triazolo[1,5‐a]pyrimidine and 6‐substituted[1,2,4]triazolo[1,5‐a]pyrimidine‐7‐amine derivatives has been synthesized via reaction of 3‐amino‐[1,2,4]triazole with enaminonitriles and enaminones. The regio orientation and the structure of the products were confirmed by spectral and analytical data and synthesis via an alternative route. The procedure proved to be simple, efficient, and high yielding, and diversities of [1,2,4]triazolo[1,5‐a]pyrimidines were obtained. 相似文献
12.
A Convenient Synthesis of Some New 1,3,4‐Thiadiazoles,Thiazoles, Pyrazolo[1,5‐a]pyrimidines,Pyrazolo[5,1‐c]triazine,and Thieno[3,2‐d]pyrimidines Containing 5‐Bromobenzofuran Moiety
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Abdou O. Abdelhamid Abdelgawad A. Fahmi Basma S. Baaiu 《Journal of heterocyclic chemistry》2016,53(4):1292-1303
1,3,4‐Thiadiazoles, pyrazolo[1,5‐a]pyrimidines, pyrazolo[5,1‐c]triazine, and thieno[3,2‐d]pyrimidines were synthesized from 1‐(5‐bromobenzofuran‐2‐yl)ethanone. The structures of the newly synthesized compounds were elucidated by elemental analysis, spectral data, chemical transformation, and alternative synthesis route whenever possible. 相似文献
13.
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
14.
Ho Sik Kim Sam Tag Kwag Kyung Ok Choi Yoshihisa Okamoto Shinnosuke Kajiwara Noriko Fujiwara Yoshihisa Kurasawa 《Journal of heterocyclic chemistry》2000,37(1):103-107
The reaction of 6‐chloro‐2‐hydrazinoquinoxaline 4‐oxide 1b with acetylacetone or benzoylacetone gave 6‐chloro‐2‐(3,5‐dimethylpyrazol‐i‐yl)quinoxaline 4‐oxide 5a or 6‐chloro‐2‐(3‐methyl‐5‐phenylpyrazol‐1‐yl)quinoxaline 4‐oxide 5b , respXectively. Compound 5a or 5b was converted into the pyrrolo[1,5‐a]quinoxaline 6a or 6b , triazolo[4,3‐a]quinoxaline 9a or 9b , and tetrazolo[1,5‐a]quinoxaline 10. 相似文献
15.
Nesrin ener Mahmut Gür M. Serdar avu Merve Zurnaci zzet ener 《Journal of heterocyclic chemistry》2019,56(3):1101-1110
7‐Amino‐3‐phenylazo‐2‐methyl‐4H‐pyrazolo[1,5‐a]pyrimidine‐5‐one ( 3 ) was synthesized by the reaction of 5‐amino‐3‐methyl‐4‐phenylazo‐1H‐pyrazole and 2‐aminobenzothiazole with ethyl cyanoacetate in acetic acid at 150°C. Four novel heterocyclic azo disperse dyes were obtained by the coupling of heterocyclic amines‐based diazonium chloride with compound 3 . They were purified and characterized by elemental analysis, FTIR, and 1H NMR. Furthermore, solvatochromic behaviors of related dyes were studied in detail by using ultraviolet–visible absorption spectrometer. The experimental data were supported by density functional theory using b3lyp/cc‐pvtz level calculations, and a detailed analysis of predicted tautomeric structures was made. 相似文献
16.
Andriy V. Shelepyuk Lyudmyla M. Potikha Volodymyr O. Kovtunenko Roman I. Zubatyuk Oleg V. Shishkin 《Journal of heterocyclic chemistry》2015,52(2):539-544
A new method based on reaction of 4‐bromobut‐2‐enoates with N‐alkylimidazoles was proposed for obtaining 1R‐1H‐imidazo[1,2‐a]pyridin‐4‐ium‐8‐olate and 1‐R‐8‐methoxy‐1H‐imidazo[1,2‐a]pyridin‐4‐ium derivatives. The structures of synthesized compounds were confirmed by 1H, 13C NMR, elemental analysis, and X‐ray data. 相似文献
17.
《Journal of heterocyclic chemistry》2017,54(3):1845-1853
Several new heterocyclic compounds such as 7‐substituted pyrazolo[1,5‐a ]pyrimidine ( 5a–e ) derivatives have been synthesized by the reactions of the versatile unreported sodium 3‐(4‐methyl‐2‐(4‐methylphenylsulfonamido)thiazol‐5‐yl)‐3‐oxoprop‐1‐en‐1‐olate (2) with amino heterocyclic ( 3a–e ) derivatives. Reaction of (2) with hydrazonyl halide ( 7a–d ) and hydroximoyl chloride ( 11a,b ) derivatives followed by reaction with hydrazine hydrate afforded pyrazolo[3,4‐d ]pyridazine and isoxazolo[3,4‐d ]pyridazine derivatives, respectively incorporating a thiazole moiety have been described. All newly synthesized compounds were elucidated by considering the data of both elemental and spectral analysis. 相似文献
18.
《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
19.
Ethyl 7‐amino‐3‐(3‐methyl‐5‐oxo‐1‐phenyl‐2‐pyrazolin‐4‐yl)‐5‐aryl‐5H‐thiazolo[3,2‐a]pyrimidine‐6‐carboxylate was hydrolyzed with an ethanolic sodium hydroxide and the sodium salt thus formed underwent cyclization with acetic anhydride to afford 2‐methyl‐7‐(3‐methyl‐5‐oxo‐1‐phenyl‐2‐pyrazolin‐4‐yl)‐5‐arylthiazolo[3,2‐a]pyrimido[4,5‐d]oxazin‐4(5H)‐one. This compound was transformed to related heterocyclic systems via its reaction with various reagents. The biological activity of the prepared compounds was tested against Gram positive and Gram negative bacteria as well as yeast‐like and filamentous fungi. They revealed in some cases excellent biocidal properties. 相似文献
20.
《Journal of heterocyclic chemistry》2018,55(1):214-225
A novel series of α‐(benzoylamino)‐β‐substituted acrylic amide derivatives of pyrazolo[1,5‐a]pyrimidine has been synthesized using a convergent multistep synthesis. The synthesized compounds were characterized by 1H NMR, 13C NMR, ESI‐MS, and IR analyses. Those new compounds were screened for their in vitro antiproliferative activity using an MTT assay analysis. Out of nine derivatives synthesized in the current study, compounds 13g , 13d , 13h , and 13i exhibited the greatest anticancer activities in HeLa and HepG2 cell lines. The in vitro anticancer activity of compound 13g against HeLa, HepG2, and MCF‐7 cell lines is superior to the marketed drugs paclitaxel and SAHA. 相似文献