共查询到20条相似文献,搜索用时 15 毫秒
1.
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
2.
A direct, concise, synthetic method for the generation of [1,2,3]triazolo[5,1-a]isoquinoline derivatives, using a selective cascade cyclization of unsymmetrical substituted 1,2-bis(phenylethynyl)benzene derivatives with NaN3, has been developed. The reaction gave different substituted [1,2,3]triazolo[5,1-a]isoquinolines in moderate to good yields. It was found that the substituents on the alkynes were important for the selectivities of the cascade cyclization sequences. 相似文献
3.
Curt Wentrup 《Helvetica chimica acta》1978,61(5):1755-1764
[1,2,3]Triazoloazines are formed by thermolysis of 5-azinyltetrazoles in the gasphase or in solution. Thus, 5-(2-pyridyl)tetrazole ( 7 ) and 5-(2-pyrazinyl)tetrazole ( 11 ) yield [1,2,3]triazolo[1,5-a]pyridine ( 9 ) and [1,2,3]triazolo[1,5-a]pyrazine ( 13 ), respectively, at 400°/10?3 - 10?5 Torr. 5-(2-Phenyl-4-quinazolinyl)tetrazole ( 15 ) gives 5-phenyl[1,2,3]triazolo[1,5-c]quinazoline ( 17 ) in 75% yield by heating under reflux in mesitylene solution. 2-(Diazomethyl)pyridine ( 8 ), a valence tautomer of 9 , can be trapped by fumaronitrile, leading to 3-(2-pyridyl)-1, 2-cyclopropanedicarbonitrile ( 19 ). The [1,2,3]triazoloazines undergo base catalysed H/D-exchange in D2O solution. 相似文献
4.
Photocyclization of 3-chloro-N-phenylbenzo[b]thiophene-2-carboxamide 10 afforded [1]benzothieno[2,3-c]-quinolin-6(5H)-one 11 which was chlorinated to 6-chloro[1]benzothieno[2,3-c]quinoline 12 followed by dechlorination to give [1]benzothieno[2,3-c]quinoline 5 . A series of 6-substituted alkoxy and thioalkoxy[1]benzothieno[2,3-c]quinoline derivatives were prepared along with the N-methyl quaternary salt 13 of 5 . 6-Chloro[1]-benzothieno[2,3-c]quinoline 12 was converted into 6-hydrazino[1]benzothieno[2,3-c]quinoline 23 which upon treatment with formic acid yielded [1]benzothieno[2,3-c][1,2,4]triazolo[4,3-a]quinoline 6 . Treatment of 23 with nitrous acid resulted in [1]benzothieno[2,3-c]tetrazolo[1,5-a]quinoline 7 . Compounds 6 and 7 are novel heterocyclic ring systems. 相似文献
5.
The uv and nmr spectral data of some 6,7,8,9,10,11-hexahydrocyclohepta[d][1,2,4]triazolo[1,5-a]pyrimidin-5-one, 5,6,7,8,9,11-hexahydrocyclohepta[e][1,2,4]triazolo[1,5-a]pyrimidin-10-one, 6,7,8,9,10,11-hexahydrocycloocta[d][1,2,4]triazolo[1,5-a]pyrimidin-5(12H)-one, 5,6,7,8,9,10-hexahydrocycloocta[e][1,2,4]triazolo[1,5-a]-pyrimidin-11(12H)-one, 6,7,8,9,10,11,12,13,14,15-decahydrocyclododeca[d][1,2,4]triazolo[1,5-a]pyrimidin-5(16H)-one and 5,6,7,8,9,10,11,12,13,14-decahydrocyclododeca[e][1,2,4]triazolo[1,5-a]pyrimidin-15(16H)-one as well as their N-benzylated derivatives representing six novel ring systems were compared to prove their structure. The N-benzylation of the highly insoluble cyclic amides to yield the isomeric N-benzyl derivatives 3/1, 3/2 and 3/3 distinguished by INAPT was performed through their readily soluble tetrabutylammonium salts. 相似文献
6.
The synthesis of novel 7-{[1,2,3]triazolo[1,5-a]pyridin-3-yl}-[1,2,3]triazolo[1,5-a]pyridines 7, 2-pyridyl-[1,2,3]triazolo[1,5-a]pyrid-7-ylmethanols 11, 3-(6-substituted-2-pyridyl)-[1,2,3]triazolo[1,5-a]pyridines 12, and 7,7′-disubstituted-3,3′-[1,2,3]triazolo[1,5-a]pyridine 20, interesting polynitrogenated ligands as potential helicating compounds or luminescent sensors, from [1,2,3]triazolo[1,5-a]pyridines is described. 相似文献
7.
T. Ramalingam M. S. R. Murty Y. V. D. Nageswar P. B. Sattur 《Journal of heterocyclic chemistry》1990,27(4):981-982
The reaction of 3 -amino-1,2,4-triazolo[4,3-a]quinoline ( II ) with diethyl ethoxymethylenemalonate and ethyl acetoacetate/ethyl trifluoroacetoacetate afforded 10-carboethoxy-9-oxo-9H-pyrimido[1′,2′:1,5][1,2,4]triazolo-[4,3-a]quinoline ( III ) and 11-methyl/trifluoromethyl-9-oxo-9H-pyrimido[1′,2′:1,5][1,2,4]triazolo[4,3-a]quinoline ( IV/V ) respectively. 2-Chloropyridine-3-carboxylic acid chloride reacted with II to yield 5-oxo-5H-pyrido-[3″,2″:5′,6′]pyrimido[1′,2′:1,5][1,2,4]triazolo[4,3-a]quinoline ( VII ), a new ring system. 相似文献
8.
Eugene S. Gladkov Svetlana N. Sirko Svetlana V. Shishkina Oleg V. Shishkin Irina V. Knyazeva Sergey M. Desenko Valentin A. Chebanov 《Monatshefte für Chemie / Chemical Monthly》2010,15(1):773-779
Abstract
An efficient and facile multicomponent procedure for the synthesis of highly substituted [1,2,3]triazolo[1,5-a]pyrimidines by reaction of equimolar amounts of aromatic aldehyde, CH-acid, and 5-amino-1,2,3-triazole in refluxing dimethylformamide is described. 相似文献9.
Alí Hadi Nazario Martín Carlos Seoane Jos L. Soto Armando Albert Flix Cano 《Journal of heterocyclic chemistry》1992,29(5):1229-1235
A one step synthesis of novel piperidinium 2-aryl[1,2,4]triazolo[1,5-a]pyridinides 6 from 2′-benzoyl-2-cyanoacetohydrazide (2) and α-substituted cinnamonitriles 3 is described. The reaction takes place by 6-exodig cyclization followed by an 5-exo-trig process to afford salts 6 . The X-ray diffraction of compound 6a reveal that the cation is strongly linked to the anion by hydrogen bonds and a characteristic partial stacking motive. 2-Aryl[1,2,4]triazolo[1,5-a]pyridines were obtained from salts 6 by treatment with hydrochloric acid. 相似文献
10.
The chemical reactivity of the [1,2,3]triazolo[1,5-a]- and [1,5-c]-pyrimidinium salts towards morpholine, water and sodium methoxide have been studied. Among others, new 1-aza and 2-azabutadienes substituted by a [1,2,3]-triazole ring were obtained in the course of the opening of the positively charged pyrimidine ring. 相似文献
11.
Sergey M. Desenko Sergey A. Komykhov Valery D. Orlov Herbert Meier 《Journal of heterocyclic chemistry》1998,35(4):989-990
The cyclocondensation of 6-acetyl-4,7-dihydro-5-methyl-7-phenyl[1,2,4]triazolo[1,5-a]pyrimidine (3) with hydroxylamine or hydrazine leads to 3a,4,9,9a-tetrahydro-3,9a-dimethyl-4-phenylisoxazolo-[5,4-d][1,2,4]triazolo[1,5-a]pyrimidine ( 4a ) and 3a,4,9,9a-tetrahydro-3,9a-dimethyl-4-phenyl-1H-pyrazolo[3,4-d][1,2,4]triazolo[1,5-a]pyrimidine ( 4b ), respectively. In the presence of methanolic hydrogen chloride, 4b undergoes a cleavage of the pyrimidine ring to yield (5-amino-1,2,4-triazol-1-yl)(3,5-dimethylpyrazol-4-yl)phenylmethane ( 5 ). The structure determination of the compounds obtained is based on 1H and 13C nmr spectra including NOE measurements. 相似文献
12.
The previously unknown polycyclic heterocyclic ring systems, namely, [1]benzothieno[2,3-c]naphtho[1,2-h]-quinoline and [1]benzothieno[2,3-c]naphtho[1,2-h][1,2,4]triazolo[4,3-a]quinoline were synthesized via photocyclization of 3-chloro-N-(1′-phenanthryl)benzo[b]thiophene-2-carboxamide. 相似文献
13.
Yasumitsu Tamura Joong-Hyup Kim Yasuyoshi Miki Hironori Hayashi Masazumi Ikeda 《Journal of heterocyclic chemistry》1975,12(3):481-483
New routes to the v-triazolo[1,5-a]pyridine and pyrazolo[1,5-a]pyridine ring systems are described. Treatment of the N-amine salts of 2-picolinealdehyde oxime or 2-pyridyl ketone oximes with polyphosphoric acid gave v-triazolo[1,5-a]pyridines in fair yields. Treatment of 2-picolyl ketones or their oximes with O-mesitylenesulfonylhydroxylamine produced directly pyrazolo-[1,5-a]pyridines. These reactions were extended to the quinoline cases. 相似文献
14.
Two series of compounds, 3-aryl- (series A, compounds 2a-j) and 3-methyl-7-aryl-[1,2,3]triazolo[1,5-a]pyridines (series B, compounds 3a-j) have been synthesized by Suzuki cross-coupling reactions, with a triazolopyridine halide and an aryl or heteroaryl boronic acid in moderate to good yields. All compounds obtained are fluorescents, the quantum yields, particularly those of compounds 3f-j, are very high. 相似文献
15.
Yoshinori Tominaga Yuichi Ichihara Tomoko Mori Chizuko Kamio Akira Hosomi 《Journal of heterocyclic chemistry》1990,27(2):263-268
The reaction of pyridinium or isoquinolinium N-ylides with methoxy-substituted ethylenes gave the corresponding indolizine and pyrrolo[2,1-a]isoquinoline derivatives bearing acetyl, aroyl, cyano, ester group at the 1-position in one step. Pyrazolo[1,5-a]pyridine, pyrazolo[1,5-a]quinoline, and pyrazolo[5,1-a]isoquinolines were also synthesized in good yields from the corresponding aromatic N-imines and methoxyethylene derivatives. 相似文献
16.
M. T. Wu M. MacCoss T. J. Ikeler J. Hirshfield B. H. Arison R. L. Tolman 《Journal of heterocyclic chemistry》1990,27(6):1559-1563
Tricyclic analogs of piperazinylthiopyrano[3,2-d]pyrimidine hypoglycemic agents were prepared. The angular tricyclic systems, 8,9-dihydro-7H-thiopyrano[2,3-e][1,2,4]triazolo[4,3-a]pyrimidine and 8,9-dihydro-7H-tetrazolo[1,5-a]thiopyrano[2,3-e]pyrimidine derivatives were synthesized from 2,4-dichloro-7,8-dihydro-6H-thiopyrano[3,2-d]pyrimidine in three step sequences. Derivatives of the linear tricyclic system, 5,6-dihydro-7H-thiopyrano[3,2-d][1,2,4]triazolo[2,3-a]pyrimidine, were prepared by condensation of 3-amino-1,2,4-triazole with ethyl 3-oxo-tetrahydropyran-2-carboxylate. The tricyclic heteroaryl-piperazines lacked significant hypoglycemic activity. 相似文献
17.
The reaction of β-lactam carbenes with 3,6-di(2-pyrimidinyl)tetrazine was studied, which produced good yields of novel 5-(3-[1,2,3]triazolo[1,5-a]pyrimidinyl)pyrrol-2-ones or pyrrolo[3′,2′:3,4]pyrrolo[1,2-a]pyrimidin-2-ones under heating at 100 °C or 140 °C, respectively. This work provided a highly efficient strategy for the construction of both [1,2,3]triazolo[1,5-a]pyrimidine and pyrrolo[3′,2′:3,4]pyrrolo[1,2-a]pyrimidine ring systems from the same reactants, and extended the application of β-lactam carbenes in the syntheses of complex heterocycles. 相似文献
18.
《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
19.
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
20.
Yoshiko Miyamoto Chiji Yamazaki Megumi Matzui 《Journal of heterocyclic chemistry》1990,27(6):1553-1557
Treatment of certain diaminomethylenehydrazones 1 of aromatic carbonyl compounds with ethyl N-cyanoimidate ( 2 ) in acetonitrile in the presence of a tertiary amine at room temperature gives the corresponding amino(N-cyanoiminomethyl)aminomethylenehydrazones 3 in high yields. The intermediate 3 can readily be cyclized to the corresponding 5-amino-2,3-dihydro[1,2,4]triazolo[1,5-a][1,3,5]triazines 4 in moderate to good yields by brief heating in acetonitrile. When the reaction of diaminomethylenehydrazones 1 with ethyl N-cyanoimidate ( 2 ) is performed at reflux temperature in the presence of a tertiary amine, 5-amino-2,3-dihydro[1,2,4]triazolo[1,5-a]1,3,5]triazines 4 can be directly obtained in moderate yields. The yields of triazolotriazine produced by the one-step synthesis are generally comparable or even higher than the overall yields from the two-step procedure. 相似文献