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1.
Hatem A. Abdel‐Aziz Nehal A. Hamdy Issa M. I. Fakhr Ahmad M. Farag 《Journal of heterocyclic chemistry》2008,45(4):1033-1037
2.
《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
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.
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.
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.
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
7.
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
8.
Jaime Portilla Diego Estupian Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2010,66(3):o133-o136
The title compound, C19H16N6, crystallizes with Z′ = 2 in the space group P21/n. The two molecules in the selected asymmetric unit are approximate mirror images of one another; most corresponding pairs of atoms are related by an approximate half‐cell translation along [100]. Each molecule contains an intramolecular N—H...N hydrogen bond and the molecules are linked into complex sheets by a combination of two intermolecular N—H...N and four C—H...π(arene) hydrogen bonds. Comparisons are made with some other 7‐aminopyrazolo[1,5‐a]pyrimidines. 相似文献
9.
Henry Insuasty Braulio Insuasty Edison Castro Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2014,70(9):908-911
In the title compound, C15H12N4OS2, the bond distances in the fused heterocyclic system show evidence for aromatic‐type delocalization in the pyrazole ring with some bond fixation in the triazine ring. The thiophenyl substituent is slightly disordered over two sets of atomic sites having occupancies of 0.934 (4) and 0.066 (4). The non‐H atoms in the entire molecule are nearly coplanar, with the planes of the furanyl substituent and the major orientation of the thiophenyl substituent making dihedral angles of 5.72 (17) and 1.8 (3)°, respectively, with that of the fused ring system. Molecules are linked into centrosymmetric R22(10) dimers by C—H...O hydrogen bonds and these dimers are further linked into chains by a single π–π stacking interaction. Comparisons are made with some related 4,7‐diaryl‐2‐(ethylsulfanyl)pyrazolo[1,5‐a][1,3,5]triazines which contain variously substituted aryl groups in place of the furanyl and thiophenyl substituents in the title compound. 相似文献
10.
Mario Cetina Ante Nagl Svjetlana Prekupec Silvana Rai‐Mali Mladen Mintas 《Acta Crystallographica. Section C, Structural Chemistry》2005,61(3):o158-o160
In the title compound, C10H14N2O3, a pyrimidine ring is fused with a piperidine ring. The pyrimidine ring is planar, whereas the piperidine ring adopts a half‐chair conformation. The molecules of the title compound are connected via O—H⋯O intermolecular hydrogen bonds into infinite zigzag chains. The pyrimidine ring is involved in three C—H⋯π interactions, which link the hydrogen‐bonded chains into a three‐dimensional framework. 相似文献
11.
Loredana Canfora Sebastien Pillet Enrique Espinosa Giuseppe Ruisi 《Acta Crystallographica. Section C, Structural Chemistry》2010,66(10):o503-o507
The molecular structure of 7‐amino‐2‐methylsulfanyl‐1,2,4‐triazolo[1,5‐a]pyrimidine‐6‐carboxylic acid is reported in two crystal environments, viz. as the dimethylformamide (DMF) monosolvate, C7H7N5O2S·C3H7NO, (I), and as the monohydrate, C7H7N5O2S·H2O, (II), both at 293 (2) K. The triazolo[1,5‐a]pyrimidine molecule is of interest with respect to the possible biological activity of its coordination compounds. While the DMF solvate exhibits a layered structural arrangement through N...O hydrogen‐bonding interactions, the monohydrate displays a network of intermolecular O...O and N...O hydrogen bonds assisted by cocrystallized water molecules and weak π–π stacking interactions, leading to a different three‐dimensional supramolecular architecture. Based on results from topological analyses of the electron‐density distribution in X—H...O (X = O, N and C) regions, hydrogen‐bonding energies have been estimated from structural information only, enabling the characterization of hydrogen‐bond graph energies. 相似文献
12.
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
13.
Muharrem Diner Namk
zdemir Süleyman Gülcemal Bekir etinkaya 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(5):m228-m230
The title complex, [RhBr(C8H12)(C21H8N2F10)], has a slightly distorted pseudo‐square‐planar geometry. The whole molecule has an approximate mirror symmetry, with the mirror plane passing through the mid‐points of the two alkene bonds of the cycloocta‐1,5‐diene (COD) ligand. The average Rh—C(COD) distance is inversely related to the magnitude of the Rh—C(benzimidazole) distance in this type of compound. The molecules are stacked in columns running along the a axis. The crystal structure contains two types of intermolecular C—H...F interactions, as well as two weak π–π stacking interactions. 相似文献
14.
Jaime Portilla Jairo Quiroga Justo Cobo John N. Low Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(8):o458-o461
In both 2,5‐dimethyl‐6,7‐dihydrobenzo[h]pyrazolo[1,5‐a]quinazoline, C16H15N3, (I), and 2‐tert‐butyl‐5‐methyl‐6,7‐dihydrobenzo[h]pyrazolo[1,5‐a]quinazoline, C19H21N3, (II), which crystallizes with Z′ = 2 in the space group P, the non‐aromatic carbocyclic rings adopt screw‐boat conformations. The molecules of (I) are linked into chains of rings by a combination of C—H...N and C—H...π(arene) hydrogen bonds, while in (II) there are no hydrogen bonds of any kind. 相似文献
15.
Jairo Quiroga Jaime Glvez Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2015,71(11):1028-1032
Pyrazolo[1,5‐c]quinazolines are fused‐quinazoline derivatives which have been reported as potential agents against neurological disorders. The normal synthesis routes to these compounds require harsh reaction conditions, long reaction times or multistep sequences. The title compound, C18H15N3S, has been prepared under very mild conditions by condensation of thiochroman‐4‐one with 5‐(2‐aminophenyl)‐1H‐pyrazole, which had itself been prepared by the reaction of hydrazine hydrate with 4‐hydroxyquinoline mediated by a brief period of microwave heating. Within the molecule in the crystal structure, the reduced pyrimidine ring adopts an envelope conformation, whereas the thiane ring adopts a half‐chair conformation. Molecules are linked into sheets by a combination of one N—H...S hydrogen bond and two independent C—H...π(arene) hydrogen bonds, which utilize the same aryl ring as the acceptor, with one C—H bond donating to each face of the ring. Comparisons are made with some related compounds. 相似文献
16.
Abdou O. Abdelhamid Shokry A. Shokry Sayed M. Tawfiek 《Journal of heterocyclic chemistry》2012,49(1):116-124
Naphtho[2,1‐b]furan‐2‐yl)(8‐phenylpyrazolo[5,1‐c][1,2,4]triazin‐3‐yl)methanone, ([1,2,4]triazolo[3,4‐c][1,2,4]triazin‐6‐yl)(naphtho[2,1‐b]furan‐2‐yl)methanone, benzo[4,5]imidazo[2,1‐c][1,2,4]triazin‐3‐yl‐naphtho[2,1‐b]furan‐2‐yl‐methanone, 5‐(naphtho[2,1‐b]furan‐2‐yl)pyrazolo[1,5‐a]pyrimidine, 7‐(naphtho[2,1‐b]furan‐2‐yl)‐[1,2,4]triazolo[4,3‐a]pyrimidine, 2‐naphtho[2,1‐b]furan‐2‐yl‐benzo[4,5]imidazo[1,2‐a]pyrimidine, pyridine, and pyrazole derivatives are synthesized from sodium salt of 5‐hydroxy‐1‐naphtho[2,1‐b]furan‐2‐ylpropenone and various reagents. The newly synthesized compounds were elucidated by elemental analysis, spectral data, chemical transformation, and alternative synthetic route whenever possible. J. Heterocyclic Chem., (2012). 相似文献
17.
Gui‐Ge Hou Li‐Ying Ma Xian‐Ping Dai 《Acta Crystallographica. Section C, Structural Chemistry》2011,67(10):m321-m323
The title compound, [Zn(C9H7N3)2(H2O)4](CF3O3S)2, contains an octahedral [ZnL2(H2O)4]2+ cationic complex with trans geometry (Zn site symmetry ), and each 5‐(3‐pyridyl)pyrimidine (L) ligand is coordinated in a monodentate fashion through the pyridine N atom. In the extended structure, these complexes, with both hydrogen‐bond acceptor (pyrimidine) and donor (H2O) functions, are linked to each other by intermolecular water–pyrimidine O—H...N hydrogen‐bonding interactions, resulting in a double chain along the crystallographic a axis. The trifluoromethanesulfonate anions are integrated into the chains via O—H...O hydrogen bonds between the coordinated water and sulfonate O atoms. These double chains are associated into a novel three‐dimensional network through interchain water–pyrimidine O—H...N hydrogen bonds. The asymmetric ligand plays an important role in constructing this unusual supramolecular structure. 相似文献
18.
Lucija Peterlin‐Mai
Mateja Malei
Matej Breznik Ale Krbav
i
《Journal of heterocyclic chemistry》2000,37(1):95-101
5‐Oxo‐5H‐[1,3]thiazolo[3,2‐a]pyrimidine‐6‐carboxylic acid ( 4 ), and 6‐methylimidazo[2,1‐b]thiazole‐5‐carboxylic acid ( 17 ) were reacted with amines 6a‐i by the reaction with oxalyl chloride and N, N‐di methyl‐formamide as a catalyst into primary and secondary amide derivatives 7‐14 and 19‐22. From compound 24 N,N'‐disubstituted ureas 26, 27 and perhydroimidazo[1,5‐c]thiazole 29 derivatives of imidazo[2,1‐b]thiazole were prepared. By nmr analysis of compound 29 , the existence of two stereoisomers resulting from both optical, due to centre of chirality at C7′a, and conformational isomerism, due to restricted C5? N6′ bond rotation were proved. 相似文献
19.
Ahmed M. Hussein 《Journal of heterocyclic chemistry》2012,49(2):446-451
An easy and efficient route for synthesis of some pyrimido[1,6‐a]pyrimidine and pyrazolo[1,5‐a]pyrimidine derivatives was described through the reaction of sodium salts of formyl ketones with 6‐aminothiouracil and 5‐aminopyrazole derivatives, respectively. The characterization of the reaction products was confirmed by using elemental analysis and spectral data. J. Heterocyclic Chem., (2012). 相似文献
20.
Dikhi Firmansyah Marzena Banasiewicz Irena Deperasińska Artur Makarewicz Prof. Boleslaw Kozankiewicz Prof. Daniel T. Gryko 《化学:亚洲杂志》2014,9(9):2483-2493
The dehydrogenative coupling of imidazo[1,2‐a]pyridine derivative has been achieved for the first time. In cases in which the most‐electron‐rich position of the electron‐excessive heterocycle was blocked by a naphthalen‐1‐yl substituent, neither oxidative aromatic coupling nor reaction under Scholl conditions enabled the fusion of the rings. The only method that converted the substrate into the corresponding imidazo[5,1,2‐de]naphtho[1,8‐ab]quinolizine was coupling in the presence of potassium in anhydrous toluene. Moreover, we discovered new, excellent conditions for this anion‐radical coupling reaction, which employed dry O2 from the start in the reaction mixture. This method afforded vertically fused imidazo[1,2‐a]pyridine in 63 % yield. Interestingly, whereas the fluorescence quantum yield (Φfl) of compound 3 , despite the freedom of rotation, was close to 50 %, the Φfl value of flat naphthalene‐imidazo[1,2‐a]pyridine was only 5 %. Detailed analysis of this compound by using DFT calculations and a low‐temperature Shpol′skii matrix revealed phosphorescence emission, thus indicating that efficient intersystem‐crossing from the lowest‐excited S1 level to the triplet manifold was the competing process with fluorescence. 相似文献