共查询到20条相似文献,搜索用时 15 毫秒
1.
Dr. Gabriel P. Da Costa Gustavo B. Blödorn Prof. Dr. Thiago Barcellos Prof. Dr. Márcio S. Silva Prof. Dr. Rafael Luque Prof. Dr. Diego Alves 《European journal of organic chemistry》2023,26(30):e202300604
We described here a simple and metal-free protocol to synthesize [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides through a two-step synthetic strategy, in which the first step uses organocatalysis (10 mol % of diethylamine or 1,8-diazabicyclo[5.4.0]undec-7-ene, while the second step involves the use of inorganic base (1.2 or 0.1 equiv. of potassium hydroxide). These reactions were performed between β-keto amides and o-carbonyl phenylazides in dimethylsulfoxide as solvent at 70 °C for 2 h. The synthetic protocol is ample, which thirteen examples of secondary [1,2,3]triazolo[1,5-a]quinoline 3-carboxamides were synthesized ranging from good to excellent yields (63-96 %), and six different tertiary [1,2,3]triazolo[1,5-a]quinolines 3-carboxamides were obtained ranging from moderate to good yields (48–76 %). 相似文献
2.
Mohammad Rahimizadeh Mehdi Pordel Mehdi Bakavoli Zahra Bakhtiarpoor Ala Orafaie 《Monatshefte für Chemie / Chemical Monthly》2009,20(2):633-638
Abstract
New imidazo[4,5-a]acridone derivatives were synthesized from the rearrangement of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles. New imidazo[4,5-a]acridines were obtained from the reaction of imidazo[4,5-a]acridones in boiling POCl3. All of these compounds exhibited antimicrobial activities comparable to streptomycin as reference drug. 相似文献3.
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
4.
Sobhi M. Gomha 《Monatshefte für Chemie / Chemical Monthly》2009,32(7):213-220
Abstract
The reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one or its 2-methylthio derivative with hydrazonoyl halides, in the presence of triethylamine, yielded 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The structure of the latter compounds was further confirmed by reaction of 2-mercapto-6,7,8,9-tetrahydro-3H-benzo[4,5]thieno[2,3-d]pyrimidin-4-one with the appropriate active chloromethylenes followed by coupling of the products with benzenediazonium chloride to afford the non-isolable azo-coupling products which converted, in situ, to 6,7,8,9-tetrahydrobenzo[4,5]thieno[2,3-d]-1,2,4-triazolo[4,5-a]pyrimidin-5-ones. The reaction mechanism was proposed and the products were screened for their biological activity. Some of the newly synthesized compounds had a moderate effect against some bacterial and fungal species. 相似文献5.
Starting from the readily available 4-bromomethy-5-carbethoxy 1,2,3-thiadiazole (V), 5-bromomethy-4-carbethoxy-1,2,3-thiadiazole (IX) and ethyl 2-aryl-5-bromomethyloxazole-4-carboxylate (XIV), 4,10-dihydro-10-oxo[1]benzoxepino[3,4-d][1,2,3]thiadiazole (Ia), 4,10-dihydro-10-oxo[1]benzothiepino[3,4-d][1,2,3]thiadiazole (Ib), 4,10-dihydro-4-oxo[1]benzothiepino[4,3-d] [1,2,3]thiazole (II), 2-aryl-4,10-dihydro-4-oxo[1]benzoxepino[4,3-d]oxazoles (XIXa-XIXc) and 2-aryl-4,10-dihydro-4-oxo[1]benzothiepino[4,3-d]oxazoles (XIXd-XIXf) were prepared. 相似文献
6.
Giuliana Biagi Irene Giorgi Oreste Livi Clementina Manera Valerio Scartoni 《Journal of heterocyclic chemistry》1999,36(5):1195-1198
Some new 1,2,3-triazolo[4,5-e]-1,2,4-triazolo[3, 4 -c]pyrimidmes were prepared starting from the corresponding 1,2,3-triazolo[4,5-d]pyrimidines via the formation of the 1,2,4-triazole ring. Thus suitable hydrazino derivatives 6 were condensed with triethyl orthoformate, triethyl orthoacetate and triethyl orthobenzoate to give the expected tricyclic derivatives 7 , 8 and 9 . Intramolecular cyclization of the ethoxycarbonylhydrazino derivatives 10 gave the tricyclic compounds 11 bearing an hydroxyl group in the 3 position. The v-triazolo-s-triazolopyrimidine derivatives were tested towards the A1 and A2A adenosine receptors in binding assays, but they did not show any receptor affinity. 相似文献
7.
Svetlana Markovi? Sonja Stankovi? Slavko Radenkovi? Ivan Gutman 《Monatshefte für Chemie / Chemical Monthly》2009,16(9):153-156
Abstract
Two mechanisms for the isomerization of cyclopenta[fg]aceanthrylene to acefluoranthene were revealed. The first pathway occurs via a cyclobutyl intermediate, whereas the second pathway involves a transition state that contains an sp 3-hybridized carbon atom. Both patterns show that the Stone-Wales rearrangement requires extremely high activation energy and indicate that the isomerization process can occur only under a drastic temperature regime. 相似文献8.
Mino R. Caira Emilian Georgescu Florentina Georgescu Florin Albota Florea Dumitrascu 《Monatshefte für Chemie / Chemical Monthly》2011,62(2):743-748
Abstract
Structural elucidation of the dihydro derivatives obtained as by-products in the classic salt method synthesis of pyrrolo[2,1-a]phthalazines and acetylenic dipolarophiles was achieved by X-ray diffraction analysis of a representative compound. In addition, new pyrrolo[2,1-a]phthalazines were obtained by a one-pot three-component reaction that avoids the formation of the dihydro derivative intermediates. 相似文献9.
Liqiang Wu Suying Ma Fulin Yan Chunguang Yang 《Monatshefte für Chemie / Chemical Monthly》2010,122(3):565-568
Abstract
An efficient synthesis of 4-aryl-3-methyl-1-phenyl-1H-benzo[g]pyrazolo[3,4-b]quinoline-5,10-diones from the three-component condensation reaction of 3-methyl-1-phenyl-1H-pyrazol-5-amine, aromatic aldehydes, and 2-hydroxy-1,4-naphthoquinone under solvent-free conditions in good to excellent yields and short reaction times using sulfamic acid as heterogeneous acid catalyst has been investigated. 相似文献10.
Quang Huy To Yong Rok Lee Sung Hong Kim 《Monatshefte für Chemie / Chemical Monthly》2012,14(2):1421-1426
Abstract
A simple and efficient method to synthesize a variety of tetrahydroquinolinones was successfully achieved by reacting various β-enaminones with several α,β-unsaturated aldehydes. This strategy can be viewed as a Br?nsted acid-mediated formal [3+3] cycloaddition. 相似文献11.
Roya Akbarzadeh Ghazaleh Imani Shakibaei Ayoob Bazgir 《Monatshefte für Chemie / Chemical Monthly》2010,15(1):1077-1081
Abstract
An efficient and simple synthesis of ferrocenyl 3-aminoimidazo[1,2-a]pyridines by the three-component reaction of ferrocenecarboxaldehyde, isocyanides, and 2-aminopyridines in the presence of a catalytic amount of InCl3 in ethanol at room temperature is reported. 相似文献12.
Yavolovskii A. A. Ivanov E. I. Mazepa A. V. Ivanov Yu. E. 《Russian Journal of General Chemistry》2003,73(9):1486-1488
[1,2,3]Triazolo[4,5-d]pyrimidine 3-oxides were synthesized by replacement of the amino group in 6-aminouracil by hydroxyamino, coupling of the resulting 6-hydroxyaminopyrimidine with benzenediazonium salts, and oxidation of 6-hydroxyamino-5-phenylazouracils with a solution of K3[Fe(CN)6] in water. 相似文献
13.
Jaroslav Kříž Jiří Dybal Emanuel Makrlík Jan Budka Petr Vaňura 《Monatshefte für Chemie / Chemical Monthly》2010,287(1):19-22
Abstract
Using 1H NMR spectroscopy together with density functional theoretical calculations, it is shown that electroneutral p-tert-butylcalix[4]arenetetraacetic acid forms an equimolar complex with a proton in the form of the H3O+ ion in nitrobenzene-d 5. Protons were offered by hydrogen bis(1,2-dicarbollyl)cobaltate and converted to hydroxonium ions by traces of water. In the resulting complex, the H3O+ cation is bound by strong hydrogen bonds to two phenoxy oxygen atoms of the parent calix[4]arene ligand and to one carbonyl oxygen of the corresponding COOH group of this ligand. 相似文献14.
Konstantin L'vovich Obydennov Tatiana Andreevna Kalinina Olga Alexandrovna Vysokova Pavel Alexandrovich Slepukhin Varvara Alexandrovna Pozdina Maria Valer'evna Ulitko Tatiana Vladimirovna Glukhareva 《Acta Crystallographica. Section C, Structural Chemistry》2020,76(8):795-809
The crystal structures of four new chiral [1,2,3]triazolo[5,1‐b][1,3,4]thiadiazines are described, namely, ethyl 5′‐benzoyl‐5′H,7′H‐spiro[cyclohexane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C19H22N4O3S, ethyl 5′‐(4‐methoxybenzoyl)‐5′H,7′H‐spiro[cyclohexane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C20H24N4O4S, ethyl 6,6‐dimethyl‐5‐(4‐methylbenzoyl)‐6,7‐dihydro‐5H‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine‐3‐carboxylate, C17H20N4O3S, and ethyl 5‐benzoyl‐6‐(4‐methoxyphenyl)‐6,7‐dihydro‐5H‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine‐3‐carboxylate, C21H20N4O4S. The crystallographic data and cell activities of these four compounds and of the structures of three previously reported similar compounds, namely, ethyl 5′‐(4‐methylbenzoyl)‐5′H,7′H‐spiro[cyclopentane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C19H22N4O3S, ethyl 5′‐(4‐methoxybenzoyl)‐5′H,7′H‐spiro[cyclopentane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate, C19H22N4O4S, and ethyl 6‐methyl‐5‐(4‐methylbenzoyl)‐6‐phenyl‐6,7‐dihydro‐5H‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine‐3‐carboxylate, C22H22N4O3S, are contrasted and compared. For both crystallization and an MTT assay, racemic mixtures of the corresponding [1,2,3]triazolo[5,1‐b][1,3,4]thiadiazines were used. The main manner of molecular packing in these compounds is the organization of either enantiomeric pairs or dimers. In both cases, the formation of two three‐centre hydrogen bonds can be detected resulting from intramolecular N—H…O and intermolecular N—H…O or N—H…N interactions. Molecules of different enantiomeric forms can also form chains through N—H…O hydrogen bonds or form layers between which only weak hydrophobic contacts exist. Unlike other [1,2,3]triazolo[5,1‐b][1,3,4]thiadiazines, ethyl 5′‐benzoyl‐5′H,7′H‐spiro[cyclohexane‐1,6′‐[1,2,3]triazolo[5,1‐b][1,3,4]thiadiazine]‐3′‐carboxylate contains molecules of only the (R)‐enantiomer; moreover, the N—H group does not participate in any significant intermolecular interactions. Molecular mechanics methods (force field OPLS3e) and the DFT B3LYP/6‐31G+(d,p) method show that the compound forming enantiomeric pairs via weak N—H…N hydrogen bonds is subject to greater distortion of the geometry under the influence of the intermolecular interactions in the crystal. For intramolecular N—H…O and S…O interactions, an analysis of the noncovalent interactions (NCIs) was carried out. The cellular activities of the compounds were tested by evaluating their antiproliferative effect against two normal human cell lines and two cancer cell lines in terms of half‐maximum inhibitory concentration (IC50). Some derivatives have been found to be very effective in inhibiting the growth of Hela cells at nanomolar and submicromolar concentrations with minimal cytotoxicity in relation to normal cells. 相似文献
15.
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
16.
Maria L. Kondratieva Natalia P. Belskaia Alexandr V. Koksharov Koen Robeyns Wim Dehaen Vasiliy A. Bakulev 《Tetrahedron》2007,63(14):3042-3048
The systematic study of oxidative cyclization of 3-hydrazono-1,3-dihydroindole-2-thiones has been carried out and a series of new 2H-[1,2,3]thiadiazolo[5,4-b]indoles has been prepared. The elaborated reaction represents an efficient method for the synthesis of fused 1,2,3-thiadiazoles. 相似文献
17.
Giuliana Biagi Irene Giorgi Oreste Livi Clementina Manera Valerio Scartoni 《Journal of heterocyclic chemistry》1997,34(1):65-69
Some new 1,2,3-triazolo[4,5-d]-1,2,4-triazolo[4,3-b]pyridazines were prepared starting from the corresponding 1,2,3-triazolo[4,5-d]pyridazines via the formation of the 1,2,4-triazole ring, by condensation of an appropriate monocarbon fragment with the 4-hydrazino substituent and the nitrogen atom in the 5 position of the heterocycle. Condensation of 4-phenylhydrazino substituted derivatives with formic acid gave zwitterionic compounds. 相似文献
18.
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 下载免费PDF全文
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
19.
Brindaban Roy Rajendra Narayan De Somjit Hazra 《Monatshefte für Chemie / Chemical Monthly》2012,41(8):119-125
Abstract
A concise synthesis of pyrrolo[1,2-f]phenanthridine-annulated polycyclic heterocycles has been achieved in good yields by palladium-catalyzed intramolecular direct arylation reaction. 相似文献20.
A. A. Voronin V. P. Zelenov A. M. Churakov Yu. A. Strelenko V. A. Tartakovsky 《Russian Chemical Bulletin》2014,63(2):475-479
Alkylation of 1-hydroxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxide 1 and its silver salt 10 with different alkylating agents (diazomethane, diazoacetone, bromoacetone, α-bromoacetophenone, methyl iodide, methyl vinyl ketone) was studied. Alkylation of compound 1 with diazo compounds and salt 10 with halocompounds results predominantly in O-alkylation products, 1-alkoxy-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 5,7-dioxides. The Michael reaction of compound 1 with methyl vinyl ketone involves the triazole nitrogen atom to give 1-(3-oxobutyl)-1H-[1,2,3]triazolo[4,5-e][1,2,3,4]tetrazine 3,4,6-trioxide. The structures of the compounds synthesized were established by 1H, 13C, 14N NMR spectroscopy and mass spectrometry. 相似文献