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1.
Yoshihisa Kurasawa Megumi Kanoh Yumiko Kamigaki Mari Okiyama Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(3):1015-1018
The reactions of the pyrazole-5-diazonium salt 3 with malononitrile and ethyl cyanoacetate gave 4-amino-3-cyano-8-ethoxycarbonylpyrazolo[5,1-c][1,2,4]triazine 7 and 4-amino-3,8-bisethoxycarbonylpyrazolo[5,1-c]-[1,2,4]triazine 8 , whose reactions with p-chloroaniline hydrochloride afforded 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)amidinopyrazolo[5,1-c][1,2,4]triazine 9 and 4-amino-8-ethoxycarbonyl-3-(p-chlorophenyl)car-bamoylpyrazolo[5,1-c][1,2,4]triazine 10 , respectively. The reactions of 7 and 8 with o-phenylenediamine di-hydrochloride provided 9-ethoxycarbonyl-13H-spiro[benzimidazole-2′(3′H),6(5H)-pyrazolo[1,5′:3,4][1,2,4]tri-azino[5,6-b][1,5]benzodiazepine] hydrochloride 11a and 9-ethoxycarbonyl-6-oxo-13H-5,6-dihydropyrazolo-[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzodiazepine 12 , respectively. The antifungal activity of the above compounds was described. 相似文献
2.
The synthesis of 1,2-dihydro-l-oxopyrazolo[1,5-d]-1,2,4-triaxine was achieved by rerrangment of 2-(5-pyrazolyl)-1,3,4-oxadiazole under alkaline condition. The cyclization of the N-carbethoxyhydrazone of the pyrazole-5-carboxaldehyde gave the 3,4-dihydro-4-oxopyrazolo[1,5-d]1,2,4-triazine. Electrophilic substitutions of the l-pyrazolotriazinome were made either on the lactam nitrogen with methylsulfate, benzylchloride and monochloracetic axid or on the pyrazole ring with bromine. The synthesis of pyrazolo[1,5-d]-1,2,4-triazine was made from teh l-pyrazolotrizinone via the l-pyrazolotrizinone. The methylation of l-pyrazolotrizinone and 8-bromo-l-pyrazolotrizinone afforded N-and S-methyl derivatives. The sysnthesis of 1,2,3,4-tetrahydropyrazolo[1,5-d]-1,2,4-triazine-1,4-diones was axhived by cyclising N-carbethoxyhydrazides of pyrrole-5-carboxylic acid. The structures of the derivatives were determined by 1H-nmr. 相似文献
3.
A. N. Gusev V. F. Shul’gin Z. M. Topilova S. B. Meshkova 《Russian Chemical Bulletin》2012,61(1):95-98
The reactions of salicylaldehyde and benzoic aldehyde with 5-(2-aminophenyl)-3-pyridyl-1H-1,2,4-triazoles were studied. The reaction products are 5-phenyl-2-pyridyl-5,6-dihydro[1,2,4]triazolo[1,5-c]quinazolines. The structures of the synthesized compounds were determined by IR spectroscopy and 1H and 13C NMR spectroscopy. The luminescence properties of solutions and solid samples were studied. 相似文献
4.
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
5.
Diaminomethylene- and aminomethylthiomethylenehydrazones [2] of cyclic ketones 1–8 readily reacted with ethoxymethylenemalononitrile to give spiro[cycloalkane-1,2′-[1,2′,4′]triazolo[1,5′-c]pyrimidine-8′-carbonitrile] derivatives 12–19 through the electrocyclic reaction of the initially formed condensation products 26 in moderate to high yields. The spiro[cyclopentanetriazolopyrimidine] derivatives underwent ring-opening at the cycloalkane moiety upon heating in solution to give 2-alkyl-5-substituted-[1,2,4]triazolo[1,5-c]pyrimidine-8′-carbonitriles 20–23 . When an alkyl substituent was introduced into the cyclopentane ring, cleavage of the spiro compounds occurred preferentially at the cyclopentane moiety between the spiro carbon and the more branched one. In contrast, the cyclohexane ring, especially of spiro-5-amino-triazolopyrimidines 17 and 18 strongly resisted to ring-opening under similar conditions, but those of 5-methylthiotriazolopyrimidines 14 gave up to 17 percent of cleavage after prolonged heating in hot ethanol. 2-t-Butyl-5-methylthio-2,3-dihydro[1,2,4]triazolo[1,5-c]pyrimidine-8-carbonitrile 25 [R3 = C(CH3)3] was highly susceptible to the cleavage even at room temperature and produced the corresponding 2-unsubstituted triazolopyrimidine 24 with loss of the t-butyl group. 相似文献
6.
Wolf-Diethard Pfeiffer Anja Bodtke Jana Mücke Annemarie Hetzheim Pavel Pazdera 《Journal of heterocyclic chemistry》1999,36(5):1327-1336
The preparation of 1,2,4-triazolo[1,5-c]quinazolines 4a-d , 5 , 8a-d by cyclocondensation of 1a-c with carboxylic acids and carboxylic anhydrides, respectively, is described. By different pathways, the 5-thioxo-5,6-dihydro-1,2,4-triazolo[1,5-c]quinazolines 4a-d react with hydrazine hydrate or amines with the formation of 5-substituted 1,2,4-triazolo[1,5-c]quinazolines 9 and 10a-d . Cyclocondensation of 9 with carboxylic acids, carboxylic anhydrides, and nitrous acid, respectively, leads to the new anellated heterocycles bis-1,2,4-triazolo[4,3-a:1,5-c]quinazoline 13 and tetrazolo [1,5-a]-1,2,4-triazolo[1,5-c]quinazoline ( 14 ). 相似文献
7.
V. M. Kisel E. O. Kostyrko O. V. Shishkin S. V. Shishkina V. A. Kovtunenko 《Chemistry of Heterocyclic Compounds》2002,38(10):1253-1262
Condensation of o-bromomethylphenylacetonitrile with arylcarbohydrazides gave, depending on the reaction conditions, 2-arylcarboxamido-1,4-dihydroisoquinoline-3(2H)-imine hydrobromides or 2-aryl-5,10-dihydro[1,2,4]triazolo[1,5-b]isoquinolines. Analogous condensation of 4-(2-bromomethylphenyl)tetrahydro-2H-pyran-4-carbonitrile and 1-(2-bromomethylphenyl)-1-cyclopentanecarbonitrile with arylcarbohydrazides gave respectively 2-aryl-2,3,5,6-tetrahydrospiro[4H-pyran-4,10'(5'H)-[1,2,4]triazolo[1,5-b]isoquinolines and 2-arylspiro[1,2,4]triazolo[1,5,b]isoquinoline-10(5'H)-1'-cyclopentanes, derivatives of new spirane heterocycles. The reaction with condensing agents of 3-imino-2,2',3,3'5',6'-hexahydrospiro[isoquinoline-4(1H),4'-4H-pyran]-2-amine and 3-imino-2,3-dihydrospiro[isoquinoline-4(1H),1'-cyclopentane]-2-amine hydrobromides, synthesized from the corresponding bromo nitriles and hydrazine, may serve as an alternative route for the synthesis of these compounds. The structure of obtained triazoloisoquinolines was established from IR, 1H and 13C NMR spectra. An X-ray crystallographic study of 2-phenylspiro[1,2,4]triazolo[1,5-b]isoquinoline-10(5H),1'-cyclopentane was carried out. 相似文献
8.
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
9.
A. S. Morkovnik T. A. Kuz’menko L. N. Divaeva G. S. Borodkin 《Russian Journal of Organic Chemistry》2013,49(6):895-903
2-(4-Methylphenyl)-4H-[1,2,4]triazolo[1,5-a]benzimidazole and its previously unknown 2-(2-furyl)- and 2-(2-thienyl)-substituted analogs were synthesized by cyclization of benzimidazole-1,2-diamine with the corresponding carboxylic acid chlorides. The IR, 1H, 13C, and 15N NMR, and mass spectra of the cyclization products in combination with the results of quantum-chemical calculations of NMR chemical shifts showed radical differences of [1,2,4]triazolo[1,5-a]benzimidazoles having no substituent on N4 from the recently reported low-melting products of oxidation of 2-amino-1-arylmethylideneaminobenzimidazoles with (diacetoxy-λ3-iodanyl)benzene, which, as we believe, were erroneously assigned analogous structure. 相似文献
10.
Sergey M. Ivanov Lyudmila M. Mironovich Mikhail E. Minyaev 《Phosphorus, sulfur, and silicon and the related elements》2020,195(8):666-676
AbstractInteraction of 8-lithio-3-tert-butyl-4-oxopyrazolo[5,1-c][1,2,4]triazin-1-ide with elemental sulfur or selenium in THF with further in situ alkylation at –97?°C followed by warming to room temperature furnished a series of 3-tert-butyl-8-X-pyrazolo[5,1-c][1,2,4]triazin-4(6H)-ones (X?=?n-BuS, n-BuSe, MeSe, PhCH2S) in good yields. 8,8'-Diselanediylbis(3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4(1H)-one) was also isolated as a by-product in these reactions. One-pot interaction of the n-BuSe substituted derivative with diborane/boron trifluoride led to reduction of the 1,2,4-triazine core and partial elimination of the alkylselanyl moiety. The structures of the synthesized products were established on the basis of IR, 1H, 13C, 2D HMBC 1H–77Se NMR and high resolution mass spectra, as well as X-ray single crystal diffraction analyses. Two of the prepared compounds were also tested for antimicrobial and antifungal activities. 相似文献
11.
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
12.
Mohamed Hilmy Elnagdi Mohamed Riffat Hamza Elmoghayar Ezzat Mohamed Kandeel Mohamed Kamal Ahmed Ibrahim 《Journal of heterocyclic chemistry》1977,14(2):227-230
3-Phenylpyrazole-5-(liazonium chloride ( 1 ) couples with α-chloro derivatives of acetylacetone, ethyl acetoacetate and aceto-o-anisidine to yield the corresponding pyrazole-5-yl hydrazonyl chloride derivatives 2a-c . Compounds 2a,b were cyclised to yield either the pyrazolo[1,5-c]-1,2,4-triazole derivatives 3a,b or the pyrazolo[1,5-c]-as-triazines 4a,b depending on the applied reaction conditions. Compound 2c cyclised only into 3c under different cyclization conditions. The pyrazolo[1,5-c]-as-triazine derivatives 4c-e could be prepared via condensation of 2a with potassium cyanide. Compound 2d reacted with aromatic thioles and with sodium benzene-sulphonate to yield the pyrazolo[1,5-c]-as-triazine derivatives 6a-d . Compound 1 reacted with activated double bond systems to yield pyrazolo[1,5-c]-as-triazines 8a,b and 9 . 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.
V. V. Konovalova O. G. Stryapunina Yu. V. Shklyaev P. A. Slepukhin A. N. Maslivets 《Russian Journal of Organic Chemistry》2013,49(2):268-271
3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with ethyl (2Z)-(3,3-dimethyl-8-oxo-2-azaspiro[4.5]deca-6,9-dien-1-ylidene)acetate to give ethyl 6′-aryl-2′-(2-hydroxyphenyl)-11′,11′-dimethyl-3′,4,4′,13′-tetraoxospiro[2,5-cyclohexadiene-1,9′-(7′-oxa-2′,12′-diazatetracyclo[6.5.1.01,5.08,12]tetradec-5′-ene)]-14′-carboxylates whose structure was confirmed by X-ray analysis. The products may be regarded as bridged analogs of pyrrolizidine alkaloids, 7′-oxa-2′,12′-diazatetracyclo[6.5.1.01,5.08,12]tetradecanes. 相似文献
15.
Yoshihisa Kurasawa Mari Okiyama Yumiko Kamigaki Megumi Kanoh Atsushi Takada Yoshihisa Okamoto 《Journal of heterocyclic chemistry》1988,25(4):1259-1262
The reactions of the 3-substituted 4-amino-8-ethoxycarbonyl[5,1-c][1,2,4]triazines 1 and 2 with o-amino-phenol hydrochloride gave the pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzoxazepines 5 and 8 . The alkylation of 5 with methyl iodide and isopropyl iodide afforded the 6-alkoxylpyrazolo[1′,5′:3,4][1,2,4]triazino-[5,6-b][1,5]benzoxazepines 6a and 6b , respectively. Refluxing of 5, 6a, 6b and 8 in hydrochloric acid/acetic acid resulted in ring transformation to produce the spiro[benzoxazole-2′(3′H),4(1H)pyrazolo[5,1-c][1,2,4]-triazines] 7a, 7b and 9 . The screening data of the above compounds was described. 相似文献
16.
Yoshihisa Kurasawa Mari Okiyama Yumiko Kamigaki Megumi Kanoh Yoshihisa Okamoto Atsushi Takada 《Journal of heterocyclic chemistry》1987,24(6):1805-1807
Novel pyrazolo[1′,5′:3,4][1,2,4]triazino[5,6-b][1,5]benzoxazepines 5, 6 and 8 were synthesized, and these compounds were converted into novel spiro[benzoxazole-2′,4(1H,3′H)-pyrazolo[5,1-c][1,2,4]triazines] 7 and 9 by ring transformation. 相似文献
17.
Irina O. Zhuravel Oleg V. Zaremba Oleksandr S. Detistov Svitlana S. Kovalenko Valentin P. Chernykh 《合成通讯》2013,43(21):3778-3784
New 5-hydroxymethyl-8-methyl-3-(3-aryl-[1,2,4]oxadiazol-5-yl)-2H-pyrano-[2,3-c]pyridin-2-ones and their esters were synthesized. The structure of obtained compounds was determined through a complete 1H NMR analysis. 相似文献
18.
Didier Legroux Jean-Paul Schoeni Christiane Pont Jean-Pierre Fleury 《Helvetica chimica acta》1987,70(1):187-195
2-Aza-1,3-dienes. Access to N-Aminoimidazoles, 3H-Pyrroles, [1,2,4]Triazolo[1,5-a]pyrazines, or Imidazo[1,2-a]pyrazines Nucleophilic attack of 5-(dialkylamino)-2-aza-1,3-diene-1,1-dicarbonitriles (or their 1-methoxycarbonyl analogous) by hydrazines or hydrazdes gives substituted N-aminoimidazoles, [1,2,4]triazolo-[1,5-a]pyrazines, or α-dihydrazino derivatives. With α-amino esters (or analogous), imidazo[1,2-a]pyrazines are produced. Addtion of cyanide anions occurs also with formation of substituted 3H-pyrroles. Structures and rationalisation of this nucleophilic attack are discussed. 相似文献
19.
Rusinov V. L. Zyryanov G. V. Egorov I. N. Ulomskii E. N. Aleksandrov G. G. Chupakhin O. N. 《Russian Journal of Organic Chemistry》2004,40(1):85-89
A new procedure has been proposed for the synthesis of 8-aryl[1,2,4]triazolo[1,5-d][1,2,4]-triazin-5(6H)-ones by reaction of 6-aryl-1,2,4-triazin-3(2H)-ones with hydrazides derived from aliphatic, aromatic, and heterocyclic carboxylic acids. The process invloves nucleophilic substitution of hydrogen (SN
H)in aryltriazinones, oxidative closure of azole ring, and Dimroth rearrangement. 相似文献
20.
Brigitte Bouteau Jean-Charles Lancelot Max Robba 《Journal of heterocyclic chemistry》1990,27(6):1649-1651
The synthesis of 1,2,4-triazolo[4,3-a] and [2,3-a]pyridines 7, 8 was achieved by cyclization of 2-hydrazino-8-nitropyridine 3a with formic acid. The 4,5,6,7-tetrahydro-1,2,4-triazolo[2,3-a]pyridine 13 and 8-amino-1,2,4-triazolo[2,3-a]pyridine 9 were obtained by catalytic hydrogenation. The reduction of triazolo pyridine 8 using stannous chloride led to the intermediate compound 10 which with acetic anhydride afforded 8-acetylamino-5-chloro-1,2,4-triazolo[2,3-a]pyridine 10a . The structure of the derivatives was determined by 1H-nmr (DMSO-d6). 相似文献