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1.
2.
H. D. Hollis Showalter 《Journal of heterocyclic chemistry》2006,43(5):1311-1317
3.
Djamila Hikem‐Oukacha Maamar Hamdi Artur M. S. Silva Rachedi Yahia 《Journal of heterocyclic chemistry》2011,48(1):63-68
3‐(Bromoacetyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one was synthesized by the reaction of dehydroacetic acid (DHAA) with bromine in glacial acetic acid. Novel heterocyclic products were synthesized from the reaction of bromo‐DHAA with alkanediamines, phenylhydrazines, ortho‐phenylenediamines, and ortho‐aminobenzenethiol. The obtained new products 3‐(2‐N‐substituted‐acetyl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐ones, 4‐hydroxy‐3‐[1‐hydroxy‐2‐(2‐phenylhydrazinyl)vinyl]‐6‐methyl‐2H‐pyran‐2‐one, 1‐(2,4‐dinitrophenyl)‐7‐methyl‐2,3‐dihydro‐1H‐pyrano[4,3‐c]pyridazine‐4,5‐dione, 3‐(3,4‐dihydroquinoxalin‐2‐yl)‐4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one/3‐(3,4‐dihydroquinoxalin‐2‐yl)‐6‐methyl‐2H‐pyran‐2,4(3H)‐dione, 6‐methyl‐3‐(3,4‐dihydroquinoxalin‐2‐yl)‐2H‐pyran‐2,4(3H)‐dione, and (E)‐3‐(2H‐benzo[b][1,4]thiazin‐3(4H)‐ylidene)‐6‐methyl‐2H‐pyran‐2,4(3H)‐dione were fully characterized by IR, 1H and 13C NMR, and mass spectra. J. Heterocyclic Chem., 2011. 相似文献
4.
A new and convenient method for the preparation of 2‐aryl‐2,3‐dihydro‐1,8‐naphthyridin‐4(1H)‐ones 4 has been developed. Thus, N‐{3‐[(2E)‐3‐arylprop‐2‐enoyl]pyridin‐2‐yl}‐2,2‐dimethylpropanamides 3 are synthesized from commercially available pyridin‐2‐amine using an easily performed three‐step sequence and are subjected to cyclization with deprotection under acidic conditions in H2O to give the desired products. Similarly, 2‐aryl‐2,3‐dihydro‐1,7‐naphthyridin‐4(1H)‐ones 8 and 2‐aryl‐2,3‐dihydro‐1,6‐naphthyridin‐4(1H)‐ones 12 can be prepared from pyridin‐3‐amine and pyridin‐4‐amine, respectively. 相似文献
5.
Lucie Sp
ilov Jan Hlav
Pavel Hradil Iveta Fryov Miroslav Soural Petr Krej
í Michal Malo 《Journal of heterocyclic chemistry》2006,43(4):1065-1070
6.
The cyclization of aryl ketone anilides 3 with diethyl malonate to affords 4‐hydroxy‐6‐phenyl‐6H‐pyrano[3,2‐c]‐pyridin‐2,5‐diones 4 in good yields. 3‐Acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 5 are obtained by ring‐opening reaction of 4‐hydroxy‐6‐phenyl‐6H‐pyrano[3,2‐c]‐pyridin‐2,5‐diones 4 in the presence of 1,2‐diethylene glycol. The reaction of 3‐acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 5 with hydroxylamine hydrochloride produces 4‐hydroxy‐3‐[N‐hydroxyethanimidoyl]‐1‐phenylpyridin‐2(1H)‐ones 6 from which 3‐alkyloxyiminoacetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 7 are obtained by reacting with alkyl bromides or iodides in the presence of anhydrous potassium carbonate with moderate yields. The similar compounds can be synthesized on refluxing 3‐acetyl‐4‐hydroxy‐1‐phenylpyridin‐2(1H)‐ones 5 with substituted hydroxylamine hydrochloride in the presence of sodium bicarbonate with good yields. Most of the synthesized compounds are characterized by IR and NMR spectroscopic methods. 相似文献
7.
Some new (S)‐1‐aryl‐N‐(1‐hydroxy‐3‐phenylpropan‐2‐yl)‐5‐methyl‐1 H‐1,2,3‐triazole‐4‐carboxamides 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h , 4i , 4j have been synthesized and established by 1H and 13C NMR, IR, MS spectra, CHN analyses, and x‐ray diffraction crystallography. The molecular conformation and packing is stabilized by interactions of intermolecular H‐bond O2’‐H2'···O1, O2‐H2···O1’ and intramolecular H‐bond N4’‐H4'N···N3’, N4’‐H4'N···O2’, N4‐H4N···N3, N4‐H4N···O2. The two rings of five numbers were formed by H‐bond in a molecular. 相似文献
8.
K. Mogilaiah J. Uma Rani B. Sakram N. Vasudeva Reddy 《Journal of heterocyclic chemistry》2006,43(2):485-488
9.
Mohamed A. Saleh Yehia A. Hafez Foad E. Abdel‐Hay Wagdy I. Gad 《Journal of heterocyclic chemistry》2003,40(6):973-978
The reaction of 3‐N‐(2‐mercapto‐4‐oxo‐4H‐quinazolin‐3‐yl)acetamide ( 1 ) with hydrazine hydrate yielded 3‐amino‐2‐methyl‐3H‐[1,2,4]triazolo[5,1‐b]quinazolin‐9‐one ( 2 ). The reaction of 2 with o‐chlorobenzaldehyde and 2‐hydroxy‐naphthaldehyde gave the corresponding 3‐arylidene amino derivatives 3 and 4 , respectively. Condensation of 2 with 1‐nitroso‐2‐naphthol afforded the corresponding 3‐(2‐hydroxy‐naphthalen‐1‐yl‐diazenyl)‐2‐methyl‐3H‐[1,2,4]triazolo[5,1‐b]quinazolin‐9‐one ( 5 ), which on subsequent reduction by SnCl2 and HCl gave the hydrazino derivative 6. Reaction of 2 with phenyl isothiocyanate in refluxing ethanol yielded thiourea derivative 7. Ring closure of 7 subsequently cyclized on refluxing with phencyl bromide, oxalyl dichloride and chloroacetic acid afforded the corresponding thiazolidine derivatives 8, 9 and 10 , respectively. Reaction of 2‐mercapto‐3‐phenylamino‐3H‐quinazolin‐4‐one ( 11 ) with hydrazine hydrate afforded 2‐hydrazino‐3‐phenylamino‐3H‐quinazolin‐4‐one ( 12 ). The reactivity 12 towards carbon disulphide, acetyl acetone and ethyl acetoacetate gave 13, 14 and 15 , respectively. Condensation of 12 with isatin afforded 2‐[N‐(2‐oxo‐1,2‐dihydroindol‐3‐ylidene)hydrazino]‐3‐phenylamino‐3H‐quinazolin‐4‐one ( 16 ). 2‐(4‐Oxo‐3‐phenylamino‐3,4‐dihydroquinazolin‐2‐ylamino)isoindole‐1,3‐dione ( 17 ) was synthesized by the reaction of 12 with phthalic anhydride. All isolated products were confirmed by their ir, 1H nmr, 13C nmr and mass spectra. 相似文献
10.
Synthesis of Heteroannulated Chromeno[2,3‐b]Pyridines: DBU Catalyzed Reactions of 2‐Amino‐6‐methylchromone‐3‐Carboxaldehyde with Some Heterocyclic Enols and Enamines
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Magdy A. Ibrahim Nasser M. El‐Gohary Sara Said 《Journal of heterocyclic chemistry》2016,53(1):117-120
New series of heteroannulated chromeno[2,3‐b]pyridines were easily and efficiently synthesized from DBU‐catalyzed condensation of 2‐amino‐6‐methylchromone‐3‐carboxaldehyde with a variety of heterocyclic enols and enamines, namely, 4‐hydroxycoumarin, 4‐hydroxy‐1‐methylquinolin‐2(1H)‐one, 2‐hydroxy‐4H‐pyrido[1,2‐a]pyrimidin‐4‐one, 4‐hydroxy‐2H‐pyrano[3,2‐c]quinoline‐2,5(6H)‐dione, 4(6)‐aminouracil and 5‐amino‐3‐methyl‐1H‐pyrazole. Structures of the new synthesized products were deduced on the basis of their analytical and spectral data. 相似文献
11.
A Novel Diastereoselective Synthesis of 6‐Aryl‐5‐hydroxy‐2,3‐dihydropyrano[2,3‐c]pyrazol‐4(1H)‐ones
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Samir Bondock 《Journal of heterocyclic chemistry》2014,51(1):127-131
A novel one‐pot diastereoselective synthesis of trans‐6‐aryl‐5‐hydroxy‐2,3‐dihydro[2,3‐c]pyrazol‐4(1H)‐ones 3a , 3b , 3c , 3d , 3e , 3f , 3g , 3h is described via the Darzens condensation reaction of 2‐chloro‐1‐(5‐hydroxy‐3‐methyl‐1‐phenyl‐1H‐pyrazol‐4‐yl)ethanone ( 2 ) with different aromatic aldehydes in aqueous basic medium. The structures of the compounds prepared were determined by analytical and spectral analyses. 相似文献
12.
Novel Bis(2‐(5‐((5‐phenyl‐1H‐tetrazol‐1‐yl)methyl)‐4H‐1,2,4‐triazol‐3‐yl)phenoxy)Alkanes: Synthesis and Characterization
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In this study, 10 different substituted aromatic bis‐benzaldehydes were synthesized by treating hydroxy benzaldehydes with various dihaloalkanes. Bis aldehydes 5a , 5b , 5c , 5d , 5e , 5f , 5g , 5h , 5i , 5j were treated with 2‐(5‐phenyl‐1H‐tetrazole‐1‐yl)acetohydrazide ( 3 ) in acidic medium and in the presence of ammonium acetate to yield a series of new isomeric bis(2‐(5‐((5‐phenyl‐1H‐tetrazol‐1‐yl)methyl)‐4H‐1,2,4‐triazol‐3‐yl)phenoxy)alkanes ( 6a , 6b , 6c , 6d , 6e , 6f , 6g , 6h , 6i , 6j ) in excellent to good yield. The newly synthesized compounds were characterized by the available spectroscopic analysis. 相似文献
13.
Cherng‐Chyi Tzeng I.‐Li Chen Yeh‐Long Chen Tai‐Chi Wang Ya‐Ling Chang Che‐Ming Teng 《Helvetica chimica acta》2000,83(2):349-358
In continuation of our search for potent antiplatelet agents, we have synthesized and evaluated several α‐methylidene‐γ‐butyrolactones bearing 3,4‐dihydroquinolin‐2(1H)‐one moieties. O‐Alkylation of 3,4‐dihydro‐8‐hydroxyquinolin‐2(1H)‐one ( 1 ) with chloroacetone under basic conditions afforded 3,4‐dihydro‐8‐(2‐oxopropoxy)quinolin‐2(1H)‐one ( 2a ) and tricyclic 2,3,6,7‐tetrahydro‐3‐hydroxy‐3‐methyl‐5H‐pyrido[1,2,3‐de][1,4]benzoxazin‐5‐one ( 3a ) in a ratio of 1 : 2.84. Their Reformatsky‐type condensation with ethyl 2‐(bromomethyl)prop‐2‐enoate furnished 3,4‐dihydro‐8‐[(2,3,4,5‐tetrahydro‐2‐methyl‐4‐methylidene‐5‐oxofuran‐2‐yl)methoxy]quinolin‐2(1H)‐one ( 4a ), which shows antiplatelet activity, in 70% yield. Its 2′‐Ph derivatives, and 6‐ and 7‐substituted analogs were also obtained from the corresponding 3,4‐dihydroquinolin‐2(1H)‐ones via alkylation and the Reformatsky‐type condensation. Of these compounds, 3,4‐dihydro‐7‐[(2,3,4,5‐tetrahydro‐4‐methylidene‐5‐oxo‐2‐phenylfuran‐2‐yl)methoxy]quinolin‐2(1H)‐one ( 10b ) was the most active against arachidonic acid (AA) induced platelet aggregation with an IC50 of 0.23 μM . For the inhibition of platelet‐activating factor (PAF) induced aggregation, 6‐{[2‐(4‐fluorophenyl)‐2,3,4,5‐tetrahydro‐4‐methylidene‐5‐oxofuran‐2‐yl]methoxy}‐3,4‐dihydroquinolin‐2(1H)‐one ( 9c ) was the most potent with an IC50 value of 1.83 μM . 相似文献
14.
The synthesis of novel 1,6‐naphthyridines 6 with potential activity against tuberculosis is described using the reaction sequence 2←4←6. Depending on the ring N‐substitution of the 4‐alkylamino‐6‐methyl‐2(1H)‐pyridones 1 and 2 the electrophilic attack of the Vilsmeier reagent gives rise to the formation of the exocyclic N‐formyl derivatives 3 from 1 and the corresponding 3‐carbaldehydes 4 from 2. 1,2‐Dihydro‐2‐imino‐7‐methyl‐1,6(6H)‐naphthyridin‐5‐ones 6a‐j are prepared by the Knoevenagel reaction of 4 with CH‐acidic nitriles 5. These reactions are carried out using a comparative study of conventional conditions (room temperature or reflux) versus microwave irradiation. 相似文献
15.
《Journal of heterocyclic chemistry》2018,55(9):2151-2156
A series of 5,6,7,8‐tetrahydro‐1,6‐naphthyridin‐2(1H)‐one derivatives hydrochloride were obtained using a convenient and mild method from 4‐piperidone monohydrate hydrochloride. The newly synthesized compounds and their derivatives were characterized by 1H NMR, 13C NMR, and high‐resolution mass spectrometry. Furthermore, cytotoxicity in vitro of the synthesized compounds were screened using MTT or CCK8 assay. The results showed that some of the compounds showed potential antitumor activity. Among of them, compound 10a had effects against tumor cells (MOLM‐13), and the half maximal inhibitory concentration value was 76 μmol/L. 相似文献
16.
Kyriakos C. Prousis Andromachi Tzani Nicolaos Avlonitis Theodora Calogeropoulou Anastasia Detsi 《Journal of heterocyclic chemistry》2013,50(6):1313-1321
The reactivity of variably substituted 2‐methyl‐4H‐3,1‐benzoxazin‐4‐ones and 2‐methyl‐4H‐pyrido[2,3‐d][1,3]oxazin‐4‐one towards carbon and oxygen nucleophiles under microwave irradiation conditions was investigated. Optimization of the reaction conditions of oxazinones with carbon nucleophiles led to the synthesis of a series of 4‐hydroxy‐quinolin‐2‐ones and 4‐hydroxy‐1,8‐naphthyridin‐2‐ones in high yields, whereas reaction with a variety of alcohols proceeded smoothly to the formation of the corresponding N‐acetyl‐anthranilates and nicotinates. 相似文献
17.
Biotransformation of (±)‐threo‐7,8‐dihydroxy(7,8‐2H2)tetradecanoic acids (threo‐(7,8‐2H2)‐ 3 ) in Saccharomyces cerevisiae afforded 5,6‐dihydroxy(5,6‐2H2)dodecanoic acids (threo‐(5,6‐2H2)‐ 4 ), which were converted to (5S,6S)‐6‐hydroxy(5,6‐2H2)dodecano‐5‐lactone ((5S,6S)‐(5,6‐2H2)‐ 7 ) with 80% e.e. and (5S,6S)‐5‐hydroxy(5,6‐2H2)dodecano‐6‐lactone ((5S,6S)‐5,6‐2H2)‐ 8 ). Further β‐oxidation of threo‐(5,6‐2H2)‐ 4 yielded 3,4‐dihydroxy(3,4‐2H2)decanoic acids (threo‐(3,4‐2H2)‐ 5 ), which were converted to (3R,4R)‐3‐hydroxy(3,4‐2H2)decano‐4‐lactone ((3R,4R)‐ 9 ) with 44% e.e. and converted to 2H‐labeled decano‐4‐lactones ((4R)‐(3‐2H1)‐ and (4R)‐(2,3‐2H2)‐ 6 ) with 96% e.e. These results were confirmed by experiments in which (±)‐threo‐3,4‐dihydroxy(3,4‐2H2)decanoic acids (threo‐(3,4‐2H2)‐ 5 ) were incubated with yeast. From incubations of methyl (5S,6S)‐ and (5R,6R)‐5,6‐dihydroxy(5,6‐2H2)dodecanoates ((5S,6S)‐ and (5R,6R)‐(5,6‐2H2)‐ 4a ), the (5S,6S)‐enantiomer was identified as the precursor of (4R)‐(3‐2H1)‐ and (2,3‐2H2)‐ 6 ). Therefore, (4R)‐ 6 is synthesized from (3S,4S)‐ 5 by an oxidation/keto acid reduction pathway involving hydrogen transfer from C(4) to C(2). In an analogous experiment, methyl (9S,10S)‐9,10‐dihydroxyoctadecanoate ((9S,10S)‐ 10a ) was metabolized to (3S,4S)‐3,4‐dihydroxydodecanoic acid ((3S,4S)‐ 15 ) and converted to (4R)‐dodecano‐4‐lactone ((4R)‐ 18 ). 相似文献
18.
Wafaa S. Hamama Alaa E. Hassanien Manal G. El‐Fedawy Hanafi H. Zoorob 《Journal of heterocyclic chemistry》2015,52(2):492-496
Syntheses of some new heterocyclic compounds incorporating quinolone moieties were achieved via reaction of 4‐hydroxy‐7‐methoxyquinolin‐2(1H)‐one ( 1 ) or 3‐bromo‐4‐hydroxy‐7‐methoxyquinolin‐2(1H)‐one ( 2 ) with binucleophilic reagents. The newly synthesized compounds were characterized by elemental analyses and spectral data (IR, 1H‐NMR and mass spectra). The newly synthesized compounds were screened for their antibacterial activity against Gram‐positive bacteria (Bacillus thuringiensis) and Gram‐negative bacteria (Escherichia coli). The results showed clearly that compounds 1 and 3 are the more potent antibacterial agents against E. coli, compounds 4 , 5 , 6 and 8 , 9 , 10 , 11 , 12 , 13 exhibited moderate activities against E. coli strain, and compounds 7 and 11 exhibited weak activities compared with Gentamicin as a well known standard drug. 相似文献
19.
Graham Smith Urs D. Wermuth Peter C. Healy 《Acta Crystallographica. Section C, Structural Chemistry》2007,63(7):o405-o407
The crystal structures of the proton‐transfer compounds of ferron (8‐hydroxy‐7‐iodoquinoline‐5‐sulfonic acid) with 4‐chloroaniline and 4‐bromoaniline, namely 4‐chloroanilinium 8‐hydroxy‐7‐iodoquinoline‐5‐sulfonate monohydrate, C6H7ClN+·C9H5INO4S−·H2O, and 4‐bromoanilinium 8‐hydroxy‐7‐iodoquinoline‐5‐sulfonate monohydrate, C6H7BrN+·C9H5INO4S−·H2O, have been determined. The compounds are isomorphous and comprise sheets of hydrogen‐bonded cations, anions and water molecules which are extended into a three‐dimensional framework structure through centrosymmetric R22(10) O—H...N hydrogen‐bonded ferron dimer interactions. 相似文献
20.
Thomas Kappe Franz Frühwirth Peter Roschger Brigitte Jocham Jenny Kremsner Wolfgang Stadlbauer 《Journal of heterocyclic chemistry》2002,39(2):391-397
Cyclocondensation of 2,3,3‐trimefhyl‐3H‐indoles 2 with malonates 3 gives 8‐hydroxy‐10,10‐dimefhyl‐10H‐pyrido[1,2‐a]indol‐6‐ones 4 , which were halogenated in position 7, 8 and 9 with sulfuryl chloride, bromine or phosphoroxychloride to give the corresponding halo‐10,10‐dimethyl‐10H‐pyrido[1,2‐a]indoles 5, 6, 7 and 8 . Amination affords the 8‐amino‐10,10‐dimethyl‐10H‐pyrido[1,2‐a]indol‐6‐one 9 . Nitration gives either the 10,10‐dimethyl‐7‐nitro‐10H‐pyrido[1,2‐a]indoles 10 or 10,10‐dimethyl‐7‐hydroxy‐10H‐pyrido[1,2‐a]indoles 11 , depending on the conditions. 相似文献