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1.
The aza‐Wittig reactions of benzophenone‐, acetophenone‐ and benzaldehyde l‐[(triphenylphosphoranyl‐idene)amino]ethylidenehydrazones (4) with phthalic anhydride, 2,3‐dimethylmaleic anhydride and 7‐oxabi‐cyclo[2,2,l]hept‐5‐ene‐2,3‐dicarboxylic anhydride ( 5a ) provide a new route to 5H,7H‐1,2,4‐triazolo[1,5‐c]‐[1,3]benzoxazepin‐7‐ones 8a‐c or 6H,8H‐1,2,4‐triazolo[1,5‐c][1,3]oxazepin‐6‐ones 8d‐h via the thermal reaction of the expected azinoimine lactones 6 . 相似文献
2.
A novel series of 2‐alkoxy(aralkoxy)‐4H‐[1,2,4]triazolo[1,5‐a]quinazolines were synthesized employing N‐cyanoimidocarbonates and 2‐hydrazinobenzoic acid as building blocks. Chemical transformation of the inherent lactam moiety in the targeted 2‐alkoxy(aralkoxy)[1,2,4]triazolo[1,5‐a]quinazolines was offered access to a variety of derivatives. J. Heterocyclic Chem., (2011). 相似文献
3.
Two series of 7‐arylazo‐7H‐3‐(2‐methyl‐1H‐indol‐3‐yl)pyrazolo[5,1‐c][1,2,4]triazol‐6(5H)‐ones 4 and 7‐arylhydrazono‐7H‐3‐(2‐methyl‐1H‐indol‐3‐yl)‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazines 7 were prepared via reactions of 4‐amino‐3‐mercapto‐5‐(2‐methyl‐1H‐indol‐3‐yl)‐1,2,4‐triazole 1 with ethyl arylhydrazono‐chloroacetate 2 and N‐aryl‐2‐oxoalkanehydrazonoyl halides 5 , respectively. A possible mechanism is proposed to account for the formation of the products. The biological activity of some of these products was also evaluated. 相似文献
4.
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
5.
Gbor Berecz Jzsef Reiter Gyula Argay Alajos Klmn 《Journal of heterocyclic chemistry》2002,39(2):319-325
Dedicated to Dr. János Császár on the occasion of his 70th birthday Ring transformation of 2‐cyanoimido‐3‐methyl‐1,3‐oxazolidine ( 10 ) yielded 5‐amino‐3‐[N‐(2‐hydrox‐yethyl)‐N‐methyl]amino‐1H‐1,2,4‐triazole ( 6 ) that was ring closed with different β‐keto esters to 2‐[N‐(2‐hydroxyethyl)‐N‐methyl]amino‐1,2,4‐triazolo[1,5‐a]pyrimidinones ( 4 ). Cyclisation of derivatives 4 led to imidazo[2′,1′:3,4][1,2,4]triazolo[1,5‐a]pyrimidines ( 2 ) and imidazo[1′,2′:2,3][1,2,4]triazolo[1,5‐a]pyrim‐idines ( 3 ) representing 10 novel ring systems. Besides spectroscopical evidence of structure of derivatives 2 and 3 X‐ray diffraction analysis of derivative 2b was also performed. 相似文献
6.
Ahmad S. Shawali Hamdi M. Hassaneen Nabil Kh. Shurrab 《Journal of heterocyclic chemistry》2008,45(6):1825-1829
7.
Hatem A. Abdel‐Aziz Nehal A. Hamdy Issa M. I. Fakhr Ahmad M. Farag 《Journal of heterocyclic chemistry》2008,45(4):1033-1037
8.
[1,3]Thiazolo[2′,3′:3,4][1,2,4]triazolo[1,5‐a]pyrimidines – A New Heterocyclic System Accessed via Bromocyclization
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Maksym Fizer Mikhailo Slivka Eduard Rusanov Alexandr Turov Vasil Lendel 《Journal of heterocyclic chemistry》2015,52(3):949-952
A facile access to novel condensed system of [1,3]thiazolo[2′,3′:3,4][1,2,4]triazolo[1,5‐a]pyrimidine is presented. This protocol consists of bromine‐assisted direct electrophilic heterocyclization of 3‐N‐allylamine‐5,6‐dihydro[1,3]thiazolo[2,3‐c][1,2,4]triazole. The bromination took place in acetic acid and gave a good yield of the target product, which was dehydrobrominated by sodium acetate action. 相似文献
9.
E. N. Ulomskiy N. R. Medvedeva A. V. Shchepochkin O. S. Eltsov V. L. Rusinov O. N. Chupakhin E. G. Deeva O. I. Kiselev 《Chemistry of Heterocyclic Compounds》2011,47(9):1164-1169
The reaction of 3-R-5-amino-1,2,4-triazoles with the ethyl ester of 2-fluoroacetoacetic acid gave 2-R-fluoro[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-ones. The reaction of a 3-R-1,2,4-triazolyl-5-diazonium salt with the ethyl ester of 2-fluoroacetoacetic acid and subsequent
cyclization of the triazolylhydrazones lead to 7-R-3-fluoro[1,2,4]triazolo[5,1-c][1,2,4]triazin-4(1H)-ones. 相似文献
10.
Syntheses of 5H-[1,2,4]triazolo[5′,1′:2,3][1,3]thiazino[5,4-c]quinolines 8, 5H-[1,2,4]triazolo[3′,4′:2)3][1,3]thiazino[5,4-c]quinolines 9, 5H-[1,2,4]triazolo[5′,1′:2,3][1,3]thiazino[5,6-c]quinolines 14 and 5H-[1,2,4]triazolo[3′,4′:2,3][1,3]thiazino[5,6-c]quinolines 15 are described starting from 4-chloro-3-chloromethylquinaldine (4) and 1,2,4-triazole-5-thiols 5 taking advantage of different reactivity of the chlorine atoms of 4 under different reaction conditions. The structures of products 8, 9, 14 and 15 and the intermediates leading to them were confirmed by desulfurization, unequivocal syntheses and nmr spectroscopy as well. 相似文献
11.
Ibrahim M. Z. Fares Ahmed E. M. Mekky Ismail A. Abdelhamid Ahmed H. M. Elwahy 《Journal of heterocyclic chemistry》2019,56(7):1958-1965
Novel bis([1,2,4]triazolo[1,5‐a]pyrimidines) and bis(2‐thioxo‐2,3‐dihydropyrido[2,3‐d]pyrimidin‐4(1H)‐ones) were prepared utilizing bis(enaminones) as precursors. The structures of the prepared compounds were elucidated by several spectral tools as well as elemental analyses. 相似文献
12.
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
13.
E. V. Vorob’ev E. S. Kurbatov V. V. Krasnikov V. V. Mezheritskii E. V. Usova 《Russian Chemical Bulletin》2006,55(8):1492-1497
7H-Pyrrolo[3,2-e][1,2,4]triazolo[1,5-c]pyrimidines were synthesized by the reactions of 2-ethoxymethyleneamino-1H-pyrrole-3-carbonitriles with acid hydrazides and by the reactions of aminoiminopyrimidines (prepared based on the above-mentioned
carbonitriles) with acid chlorides.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1438–1443, August, 2006. 相似文献
14.
Montserrat Heras David Font Anthony Linden JosM. Villalgordo 《Helvetica chimica acta》2003,86(9):3204-3214
The synthesis of novel triazolo[1,5‐a]triazin‐7‐ones is presented. Starting from 3‐amino‐5‐sulfanyl‐1,2,4‐triazole, the synthetic sequence involved alkylation with benzyl bromide, reaction with p‐nitrophenyl chloroformate followed by treatment with a primary amine, and condensation with diethoxymethyl acetate. Final oxidation of the thioether moiety with 3‐chloroperbenzoic acid provided 2‐(benzylsulfonyl)[1,2,4]triazolo[1,5‐a][1,3,5]triazin‐7‐ones 5a and 5b in good overall yields. Treatment of 5a and 5b with secondary amines provided highly functionalized [1,2,4]triazoles through an unexpected triazinone ring opening. A mechanism for this transformation is proposed. 相似文献
15.
Maria Rosaria Del Giudice Anna Borioni Carlo Mustazza Franco Gatta 《Journal of heterocyclic chemistry》1994,31(6):1503-1507
A number of 2-aryl-substituted pyrido[3,2-e] and [4,3-e][1,2,4]triazolo[1,5-c]pyrimidines and [1,2,4]triazolo[1,5-c]pteridines 11,12a,b,e , their corresponding 5-carbonyl derivatives 7,8a,b,e and some pyrimido[5,4-e][1,2,4]triazolo[1,5-c]pyrimidin-5-ones 7,8c,d have been synthesized, according to different pathways. The new tricyclic heterocycles were prepared with the aim of studying their possible benzodiazepine receptors affinity. 相似文献
16.
5,7-Diamino[1,3,4]thiadiazolo[3,2-a]pyrirnidinium chloride 2 , 7-amino[1,2,4]triazolo[1,5-c]pyrimidine-5(6H)-thiones 3 and the 5(6H)-one derivative 4a were synthesized by the reaction of 1,4,6-triaminopyrimidine-2(1H)-thione 1 with phosphoryl chloride and N,N-dimethylacylamides. Further, compounds 4 were prepared from 2, 3 or 1,4,6-triaminopyrimidin-2(1H)-one 6 by the treatment with the above reagents. Compounds 3 and 4 were converted to 7-amino[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-ones 5 . 相似文献
17.
V. A. Tartakovsky A. E. Frumkin A. M. Churakov Yu. A. Strelenko 《Russian Chemical Bulletin》2005,54(3):719-725
Thermal cyclization of 3-R-5-chloro-1,2,4-triazoles (R = Cl, Ph) afforded 2,6,10-tri-R- tris[1,2,4]triazolo[1,5-a:1′,5′c:1″,5″-e][1,3,5]triazines 5 (R = Ph) and 7 (R = Cl). These compounds are first representatives of this class of heterocycles, whose structures were unambiguously established. Treatment of these compounds with nucleophiles (H2O/NaOH, NH3) results in the triazine ring opening to give compounds consisting of three 1,2,4-triazole rings linked in a chain. For example, treatment of cyclic compound 5 with aqueous alkali affords 3-phenyl-1-3-phenyl-1-(3-phenyl-1H-1,2,4-triazol-5-yl)-1,2,4-triazol-5-yl-1H-1,2,4-triazol-5-one. Treatment of 3,7,11-triphenyltris[1,2,4]triazolo[4,3-a:4′,3′c:4″,3″-e][1,3,5]triazine (2) with HCl/SbCl5 leads to the triazine ring opening giving rise to 5-(3-chloro-5-phenyl-1,2,4-triazol-4-yl)-3-phenyl-4-(5-phenyl-1H-1,2,4-triazol-3-yl)-1,2,4-triazole. Thermal cyclization of the latter produces 3,7,10-triphenyltris[1,2,4]triazolo[1,5-a:4′,3′c:4″,3″-e][1,3,5]triazine (13). Thermolysis of both cyclic compound 2 and cyclic compound 13 is accompanied by the Dimroth rearrangement to yield 3,6,10-triphenyl-tris[1,2,4]triazolo[1,5-a:1′, 5′-c:4″,3″-e][1,3,5]triazine (14). Compounds 13 and 14 are the first representatives of cyclic compounds with this skeleton. 13C NMR spectroscopy allows the determination of the isomer type in a series of tris[1,2,4]triazolo[1,3,5]triazines.__________Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 706–712, March, 2005. 相似文献
18.
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
19.
Regioselectivity of the reactions of 1H-1,2,4-triazol-3-amines with 2-acyl-5,5-dimethylcyclohexane-1,3-diones and 2-dimethylaminomethylidene-5,5-dimethylcyclohexane-1,3-dione was studied. In all cases, the products were substituted 8,9-dihydro[1,2,4]triazolo[1,5-a]quinazolin-6(7H)-ones whose structure was determined by 1H and 13C NMR spectroscopy. 相似文献
20.
Antonio Salgado Carmen Varela Ana María García Collazo Paolo Pevarello 《Magnetic resonance in chemistry : MRC》2010,48(8):614-622
The condensation of malonoaldehyde derivatives with either a 3‐amino‐[1,2,4]‐triazole or a 3,5‐diamino‐[1,2,4]‐triazole precursor was studied. In agreement with previous reports, two different bicycles, namely, bearing the regioisomeric [1,2,4]triazolo[1,5‐a]pyrimidine ( 1 ) or[1,2,4] triazolo [4,3‐a]pyrimidine ( 2 ) structural surrogates, could be obtained. We found that, depending on the triazole precursor, only one regioisomer resulted, either of the 1 or 2 series. We also observed that these two structural surrogates could be unambiguously differentiated by indirectly measuring their 15N chemical shifts by 1H? 15N HMBC experiments. The occasional conversion of [1,2,4]triazolo[4,3‐a]pyrimidines to the [1,2,4]triazolo[1,5‐a]pyrimidine counterparts could be unequivocally determined by 15N NMR data. Copyright © 2010 John Wiley & Sons, Ltd. 相似文献