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1.
The 1H‐pyrazole‐3‐carboxylic acid 1 was converted via reactions of its acid chloride 3 with various asymmetrical disubstituted urea and alcohol derivatives into the corresponding novel 4‐benzoyl‐N‐(N′,N′‐dialkylcarbamyl)‐1‐(4‐methoxyphenyl)‐5‐phenyl‐1H‐pyrazole‐3‐carboxamide 4a , b and alkyl 4‐benzoyl‐1‐(4‐methoxyphenyl)‐5‐phenyl‐1H‐pyrazole‐3‐carboxylate 7a‐c , respectively, in good yields (57%‐78%). Friedel‐Crafts reactions of 3 with aromatic compouns for 15 min.‐2 h led to the formation of the 4‐3‐diaroyl‐1‐(4‐hydroxyphenyl)‐5‐phenyl‐1H‐pyrazoles 9a‐c , 4‐benzoyl‐1‐(4‐methoxyphenyl)‐3‐aroyl‐5‐phenyl‐1H‐pyrazoles 10a , b and than from the acylation reactions of 9a‐c were obtained the 3,4‐diaroyl‐1‐(4‐acyloxyphenyl)‐5‐phenyl‐1H‐pyrazoles 13a‐d . The structures of all new synthesized compounds were established by NMR experiments such as 1H, and 13C, as well as 2D COSY and IR spectroscopic data, and elemental analyses. All the compounds were evaluated for their antimicrobial activities (agar diffusion method) against eight bacteria and two yeasts.  相似文献   

2.
A series of some fused heterocycles originated from pyrazolopyrimidines were synthesized using 4‐amino1‐methyl‐3‐propyl‐1H‐pyrazole‐5‐carboxamide as a starting material. The nucleophilic substitution reactions with different amino acids followed by cyclization and Suzuki–Miyaura cross‐coupling reactions with different aryl boronic acids of 7‐chloro‐5‐(4‐chlorophenyl)‐1‐methyl‐3‐propyl‐1H‐pyrazolo[4,3‐d]pyrimidine were performed. Also, the oxidative cyclization reactions of 1‐(5‐(4‐chlorophenyl)‐1‐methyl‐3‐propyl‐1H‐pyrazolo[4,3‐d]pyrimidin‐7‐yl)hydrazine with different aldehydes in the presence of diacetoxy iodobenzene are described. All the synthesized compounds were characterized by analytical and spectroscopic methods.  相似文献   

3.
The title compound, C16H23N5O3S, ethyl 5-amino-1-(5‘-methyl-1‘-t-butyl-4‘-pyrazolyl)carbonyl-3-methylthio-1H-pyrazole-4-carboxylate (5) has been synthesized by the treatment of ethyl 2-cyano-3,3-dimethylthioacrylate with 1-t-butyl-5-methyl-4-hydrazinocarbonylpyrazole (4) in refluxed ethanol. The possible mechanism of the above reaction was also discussed. The results of biological test show that the title compound has fungicidal and plant growth regulation activities.  相似文献   

4.
The hydrazones 3a,b , prepared from phenylhydrazine ( 1 ) and dialkyl 2‐oxopropane‐1,3‐dicarboxylate ( 2a,b ) were converted in concentrated sulfuric acid at ?5 °C into a mixture of alkyl (3‐carboxyindol‐2‐yl)acetates ( 5a,b ), and ethyl (5‐ethoxy‐1‐phenyl‐1H‐pyrazol‐3‐yl)acetate 6 . The hydrazone 8 , prepared from 1 and ethyl acetoacetate ( 7 ) was transformed under the same conditions into a mixture of five compounds: ethyl 2‐methylindol‐3‐carboxylate ( 9 ), 2‐methylindol‐3‐carboxylic acid ( 10 ), 2‐methylindol ( 11 ), 5‐ethoxy‐3‐methyl‐1‐phenyl‐1H‐pyrazole ( 12 ), and 3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐one ( 13 ).  相似文献   

5.
The title diastereoisomers, methyl 5‐(S)‐[2‐(S)‐methoxy­carbonyl)‐2,3,4,5‐tetra­hydro­pyrrol‐1‐yl­carbonyl]‐1‐(4‐methyl­phenyl)‐4,5‐di­hydro­pyrazole‐3‐carboxyl­ate and methyl 5‐(S)‐[2‐(R)‐methoxycarbonyl)‐2,3,4,5‐tetrahydropyrrol‐1‐ylcarbonyl]‐1‐(4‐methyl­phenyl)‐4,5‐di­hydro­pyrazole‐3‐carboxylate, both C19H23N3O5, have been studied in two crystalline forms. The first form, methyl 5‐(S)‐[2‐(S)‐methoxy­carbonyl)‐2,3,4,5‐tetrahydropyrrol‐1‐ylcarbonyl]‐1‐(4‐methylphenyl)‐4,5‐di­hydro­pyrazole‐3‐carboxyl­ate–methyl 5‐(S)‐[2‐(R)‐methoxy­carbonyl)‐2,3,4,5‐tetra­hydro­pyrrol‐1‐yl­carbonyl]‐1‐(4‐methylphenyl)‐4,5‐dihydropyrazole‐3‐carboxylate (1/1), 2(S),5(S)‐C19H23N3O5·2(R),5(S)‐C19H23N3O5, contains both S,S and S,R isomers, while the second, methyl 5‐(S)‐[2‐(S)‐methoxycarbonyl)‐2,3,4,5‐tetrahydro­pyrrol‐1‐ylcarbonyl]‐1‐(4‐methyl­phenyl)‐4,5‐di­hydro­pyrazole‐3‐carboxyl­ate, 2(S),5(S)‐C19H23N3O5, is the pure S,S isomer. The S,S isomers in the two structures show very similar geometries, the maximum difference being about 15° on one torsion angle. The differences between the S,S and S,R isomers, apart from those due to the inversion of one chiral centre, are more remarkable, and are partially due to a possible rotational disorder of the 2‐­(methoxycarbonyl)tetrahydropyrrole group.  相似文献   

6.
5‐Benzylamino‐3‐tert‐butyl‐1‐phenyl‐1H‐pyrazole, C20H23N3, (I), and its 5‐[4‐(trifluoromethyl)benzyl]‐, C21H22F3N3, (III), and 5‐(4‐bromobenzyl)‐, C20H22BrN3, (V), analogues, are isomorphous in the space group C2/c, but not strictly isostructural; molecules of (I) form hydrogen‐bonded chains, while those of (III) and (V) form hydrogen‐bonded sheets, albeit with slightly different architectures. Molecules of 3‐tert‐butyl‐5‐(4‐methylbenzylamino)‐1‐phenyl‐1H‐pyrazole, C21H25N3, (II), are linked into hydrogen‐bonded dimers by a combination of N—H...π(arene) and C—H...π(arene) hydrogen bonds, while those of 3‐tert‐butyl‐5‐(4‐chlorobenzylamino)‐1‐phenyl‐1H‐pyrazole, C20H22ClN3, (IV), form hydrogen‐bonded chains of rings which are themselves linked into sheets by an aromatic π–π stacking interaction. Simple hydrogen‐bonded chains built from a single N—H...O hydrogen bond are formed in 3‐tert‐butyl‐5‐(4‐nitrobenzylamino)‐1‐phenyl‐1H‐pyrazole, C20H22N4O2, (VI), while in 3‐tert‐butyl‐5‐(3,4,5‐trimethoxybenzylamino)‐1‐phenyl‐1H‐pyrazole, C23H29N3O3, (VII), which crystallizes with Z′ = 2 in the space group P, pairs of molecules are linked into two independent centrosymmetric dimers, one generated by a three‐centre N—H...(O)2 hydrogen bond and the other by a two‐centre N—H...O hydrogen bond.  相似文献   

7.
The synthesis of a new series of 4‐aryl‐3‐chloro‐2‐oxo‐N‐[3‐(10H‐phenothiazin‐10‐yl)propyl]azetidine‐1‐carboxamides, 4a – 4m , is described. Phenothiazine on reaction with Cl(CH2)3Br at room temperature gave 10‐(3‐chloropropyl)‐10H‐phenothiazine ( 1 ), and the latter reacted with urea to yield 1‐[3‐(10H‐phenothiazin‐10‐yl)propyl]urea ( 2 ). Further reaction of 2 with several substituted aromatic aldehydes led to N‐(arylmethylidene)‐N′‐[3‐(phenothiazin‐10‐yl)propyl]ureas 3a – 3m , which, on treatment with ClCH2COCl in the presence of Et3N, furnished the desired racemic trans‐2‐oxoazetidin‐1‐carboxamide derivatives 4a – 4m . The structures of all new compounds were confirmed by IR, and 1H‐ and 13C‐NMR spectroscopy, FAB mass spectrometry, and chemical methods.  相似文献   

8.
Three related compounds containing a pyrazole moiety with vicinal phenyl rings featuring a methyl­sulfonyl substituent are described, namely 3‐methyl‐1‐[4‐(methyl­sulfonyl)­phenyl]‐5‐phenyl‐1H‐pyrazole, C17H16N2O2S, ethyl 1‐[4‐(methyl­sul­fonyl)­phenyl]‐5‐phenyl‐1H‐pyrazole‐3‐carboxyl­ate, C19H18N2O4S, and 1‐[4‐(methyl­sulfonyl)­phenyl]‐3‐[3‐(morpholino)­phenoxy­methyl]‐5‐phenyl‐1H‐pyrazole, C27H27N3O4S. The design of these compounds was based on celecoxib, a selective cyclo­oxy­genase‐2 (COX‐2) inhibitor, in order to study the influence of various substituents on COX‐2 and 5‐lipoxy­genase (5‐LOX) inhibition.  相似文献   

9.
Cyclizations of α,β‐unsaturated ketones with aminoguanidine under neutral conditions were examined. In contrast to literature reports of 1,2,4‐triazines as reaction products, formation of 5‐aryl‐4,5‐dihy‐dro‐3‐methyl‐1H‐pyrazole‐1‐carboximidamides and carboxamides was observed. An explanation based on the Hard‐Soft Acid‐Base principle is presented and the probable causes of divergent reaction pathways are discussed.  相似文献   

10.
Cyclohexylamine reacts with 5‐chloro‐3‐methyl‐1‐(pyridin‐2‐yl)‐1H‐pyrazole‐4‐carbaldehyde to give 5‐cyclohexylamino‐3‐methyl‐1‐(pyridin‐2‐yl)‐1H‐pyrazole‐4‐carbaldehyde, C16H20N4O, (I), formed by nucleophilic substitution, but with 5‐chloro‐3‐methyl‐1‐phenyl‐1H‐pyrazole‐4‐carbaldehyde the product is (Z)‐4‐[(cyclohexylamino)methylidene]‐3‐methyl‐1‐phenyl‐1H‐pyrazol‐5(4H)‐one, C17H21N3O, (II), formed by condensation followed by hydrolysis. Compound (II) crystallizes with Z′ = 2, and in one of the two independent molecular types the cyclohexylamine unit is disordered over two sets of atomic sites having occupancies of 0.65 (3) and 0.35 (3). The vinylogous amide portion in each compound shows evidence of electronic polarization, such that in each the O atom carries a partial negative charge and the N atom of the cyclohexylamine portion carries a partial positive charge. The molecules of (I) contain an intramolecular N—H...N hydrogen bond, and they are linked by C—H...O hydrogen bonds to form sheets. Each of the two independent molecules of (II) contains an intramolecular N—H...O hydrogen bond and each molecular type forms a centrosymmetric dimer containing one R22(4) ring and two inversion‐related S(6) rings.  相似文献   

11.
A series of novel 1‐methyl‐3‐(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles was synthesized in three steps from 5‐(1‐methyl‐1H‐indazol‐3‐yl)‐4‐phenyl‐2H‐1,2,4‐triazole‐3(4H)‐thiones. 5‐(1‐Methyl‐1H‐indazol‐3‐yl)‐4‐phenyl‐2H‐1,2,4‐triazole‐3(4H)‐thiones were converted into 1‐methyl‐3‐(5‐(methylsulfonyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles upon methylation followed by treatment with aq. KMnO4. The reaction of 1‐methyl‐3‐(5‐(methylsulfonyl)‐4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles with Raney nickel resulted in desulphonylation to afford corresponding 1‐methyl‐3‐(4‐phenyl‐4H‐1,2,4‐triazol‐3‐yl)‐1H‐indazoles. All the new synthesized compounds were characterized by spectral techniques.  相似文献   

12.
Mol­ecules of 1‐acetyl‐3‐ferrocenyl‐5‐methyl‐1H‐pyrazole, [Fe(C5H5)(C11H11N2O)], form a centrosymmetric dimer generated by a combination of one C—H⋯π(pyrazole) and one C—H⋯π(cyclo­penta­dienyl) inter­action. The dimers are linked by C—H⋯π inter­actions, involving the pyrazole rings as acceptors, into layers parallel to (10). Mol­ecules of 1‐acetyl‐5‐ferrocenyl‐3‐(2‐pyrid­yl)‐1H‐pyrazole, [Fe(C5H5)(C15H12N3O)], are linked by C—H⋯O inter­actions into a chain running in the [010] direction. Two chains of this type passing through each unit cell are connected by O⋯π(pyridyl) inter­actions into an [010] double chain.  相似文献   

13.
Microwave‐assisted treatment of ethyl 5‐hydroxy‐1‐phenyl‐1H‐pyrazole‐4‐carboxylate with excess primary aliphatic amines in 1‐propanol at 140°C and with excess pyrrolidine or piperidine in 2‐methoxyethanol at 180°C produced the corresponding carboxamides in good yields.  相似文献   

14.
Efficient heterocyclization of methyl 7,7,7‐trifluoro‐4‐methoxy‐6‐oxo‐4‐heptenoate and methyl 7,7,7‐trichloro‐4‐methoxy‐6‐oxo‐4‐heptenoate into isoxazole and pyrazole derivatives that represent a new type of glutamate‐like 3‐(trihalomethylated‐1,2‐azol‐3‐yl)propanoate is reported. Preparation of the key methyl 7,7,7‐trihalo‐4‐methoxy‐6‐oxohept‐4‐enoate precursors from levulinic acid is also described. The synthetic potential of this synthetic protocol was indicated by the production of several methyl and ethyl 3‐(isoxazol‐3‐yl)propanoates and 3‐(1H‐pyrazol‐3‐yl)propanoates, and the respective acid derivatives, in good (70–95%) yields. The crystal structure for ethyl 5‐(3‐ethoxy‐3‐oxopropyl)‐1H‐pyrazole‐3‐carboxylate ( 10c ) has been determined by monocrystal X‐ray diffraction analysis. The N–HH intermolecular hydrogen bonds join the molecules into catamer.  相似文献   

15.
The 1H and 13C NMR resonances of 22 5‐(5‐substituted‐2‐nitrophenyl)‐1H‐pyrrole‐2‐carboxamides, 22 5‐(5‐substituted‐2‐aminophenyl)‐1H‐pyrrole‐2‐carboxamides, and 9 5‐phenyl‐1H‐pyrrole‐2‐carboxamides were assigned completely using the concerted application of one‐ and two‐dimensional experiments (DEPT, gs‐HMQC and gs‐HMBC). NOE studies and conformational analysis confirm the preferred conformations of such compounds. Copyright © 2009 John Wiley & Sons, Ltd.  相似文献   

16.
This paper presents the synthesis of a series of 5,6‐dihydro‐4H,8H‐pyrimido[1,2,3‐cd]purine‐8,10(9H)‐dione ring system derivatives with a [1,2,3]triazole ring bonded in position 2. The procedure is based on cycloaddition of substituted alkyl azides to the terminal triple bond of 5,6‐dihydro‐2‐ethynyl‐9‐methyl‐4H,8H‐pyrimido[1,2,3‐cd]purine‐8,10(9H)‐dione ( 4 ). This cycloaddition produced two regioisomers ?5,6‐dihydro‐9‐methyl‐2‐(1‐substituted‐1H‐[1,2,3]triazol‐5‐yl)‐4H,8H‐pyrimido[1,2,3‐cd]purine‐8,10(9H)‐dione ( 7 ) and 2‐(1‐substituted‐1H‐[1,2,3]triazol‐4‐yl) derivative 8 . The required 2‐ethynyl deriva tive 4 was obtained from the starting 2‐unsubstituted compound 1 by bromination to yield the 2‐bromo derivative 2 , which was converted by Sonogashira reaction to trimethylsilylethyne 3 and finally, the protective trimethylsilyl group was removed by hydrolysis.  相似文献   

17.
New series of (thieno[2,3‐c]pyrazolo‐5‐yl)‐[1,2,4]triazolo[3,4‐b][1,3,4]thiadiazoles 10a , 10b , 10c and (thieno[2,3‐c]pyrazol‐5‐yl)‐1,3,4‐oxadiazol‐3(2H)‐yl)ethanones 6a , 6b , 6c has been synthesized from thieno[2,3‐c]pyrazole‐5‐carbohydrazide 3 by multistep reaction sequence. (5‐Aryl‐1,3,4‐oxadiazol‐2‐yl)‐1H‐thieno[2,3‐c]pyrazoles 4a , 4b , 4c were also synthesized from thieno[2,3‐c]pyrazole‐5‐carbohydrazide 3 by cyclization with various aromatic carboxylic acids. The hydrazide 3 was obtained by reaction of thieno[2,3‐c]pyrazole‐5‐carboxylate 2 with hydrazine hydrate in good yield, and compound 2 was obtained by the reaction of 5‐chloro‐3‐methyl‐1‐phenyl‐1H‐pyrazole‐4‐carbaldehyde 1 and 2‐ethyl thioglycolate in presence of sodium alcoholate in good yield.  相似文献   

18.
The 1H‐pyrazole‐3‐carboxylic acid 2 , obtained from the furan‐2,3‐dione 1 and N‐Benzylidene‐N'‐(3‐nitrophenyl) hydrazine, was converted via reactions of its acid chloride 3 with various alcohols or N‐nucleo‐philes into the corresponding ester or amide derivatives 4 or 5 , respectively. Nitrile 6 and anilino‐pyrazole acid 7 derivatives of 2 were also obtained by dehydration of 5a in a mixture of SOCl2 with DMF and reduction of 2 with sodium polysulphide, respectively. While cyclocondensation reactions of 2 or 7 with phenyl hydrazine or hydrazine hydrate and 6 with only anhydrous hydrazine lead to derivatives of pyrazolo[3,4‐d]‐pyridazinone 8 and pyrazolo[3,4‐d]pyridazine amine 9 , respectivel. The reaction of 2 with 2‐hydrazinopyri‐dine provided hydrazono‐pyrazole acid derivative 10 , which was decarboxylated to give hydrazono‐pyra‐zole derivative 11 . Pyrazolo[4,3‐d]oxazinone 12 and 2‐quinolyl pyrazolo[3,4‐d]pyridazine 13 derivatives were also prepared by cyclocondensation reactions of 2 with hydroxylamine hydrochloride and 7 with acetaldehyde, respectively.  相似文献   

19.
Two series, totaling twelve, of new compounds, ethyl 1‐aroyl/(aroylmethyl)‐5‐methyl‐3‐methylthiopyrazole‐4‐carboxylates ( 5 / 6 ), have been synthesized via highly regioselectively acylation and alkylation reactions of ethyl 3‐methyl‐5‐methylthio‐1 H‐pyrazole‐4‐carboxylate ( 2a ) with aroyl chloride ( 3 ) and eco‐friendly reagents alpha‐tosyloxysubstituted acetophenones ( 4 ), respectively, and a green protocol has been developed. The acylation reactions were carried out under ultrasound irradiation, and the alkylation reactions were under microwave irradiation and ultrasound irradiation, respectively. Conventional reaction conditions, as well as the use of alpha‐bromosubstituted acetophenone ( 4 ′) have also been applied in the synthesis of some randomly selected compounds in both series and have generated identical compounds correspondingly. Unexpected structures of compounds were unambiguously determined by X‐ray crystallographic analysis.  相似文献   

20.
A series of substituted N‐(4‐substituted‐benzoyl)‐N‐[3‐(1‐methyl‐1H‐imidazol‐2‐yl)propyl]amines ( 13 ) and N‐arylsulfonyl‐N‐[3‐(1‐methyl‐1H‐imidazol‐2‐yl)propyl]amines ( 14 ) were prepared from the reaction of 3‐(1‐methyl‐1H‐imidazol‐2‐yl)propan‐1‐amine ( 7 ) with substituted benzoyl chloride or substituted‐benzene sulfonyl chloride respectively. Compound 7 was prepared by two independent methods.  相似文献   

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