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1.
The reaction of methyl 2‐(3‐chloro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)propenoate ( 2a ) with primary amines gave 4‐chloro‐5‐hydroxy‐3‐methoxycarbonyl‐1H‐benzo[g]indoles 5a‐f as major compounds and 3‐methoxycarbonyl‐4,9‐dioxo‐2,3,4,9‐tetrahydro‐1H‐benzo[f]indoles 6a‐d as minor ones. Whereas the reaction of 3‐(3‐chloro‐1,4‐dioxo‐1,4‐dihydronaphthalen‐2‐yl)‐3‐buten‐2‐one ( 2b ) with primary amines afforded the corresponding 1H‐benzo[g]indoles 5g‐i as major products and 3‐acetyl‐4,9‐dihydro‐4,9‐dioxo‐1H‐benzo[f]indoles 7g, h as minor products. 相似文献
2.
Regioselective Synthesis of Amino Substituted Indazolo[2,1‐b]phthalazine‐triones and Pyrazolo[1,2‐b]phthalazine‐2‐carbonitriles Catalyzed by 2‐1′‐Methylimidazolium‐3‐yl‐1‐ethyl Sulfate
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Yu Wan Chao Wang Xiao‐xiao Zhang Jingjing Shi Shu‐ying Huang Gui‐Xiang Liu Liang‐feng Chen Ling‐ling Zhao Hai‐ying Wang Hui Wu 《Journal of heterocyclic chemistry》2014,51(Z1):E77-E83
The regioselective reactions of luminol with 1,3‐cyclohexanedione (or malononitrile) and aromatic aldehydes catalyzed by 2‐1′‐methylimidazolium‐3‐yl‐1‐ethyl sulfate were developed to synthesize 7‐amino‐3,4‐dihydro‐2H‐indazolo[2,1‐b]phthalazine‐1,6,11(13H)‐triones and 3,9‐diamino‐5,10‐dihydro‐5,10‐dioxo‐1H‐pyrazolo[1,2‐b]phthalazine‐2‐carbonitriles in good to excellent yields in short times. 相似文献
3.
Kamal M. El‐Shaieb 《中国化学会会志》2007,54(5):1353-1358
When 2,3‐dichloro‐1,4‐naphthoquinone (DCHNQ) ( 1 ) is allowed to react with 1‐phenylbiguanide (PBG) ( 2 ), 4‐chloro‐2,5‐dihydro‐2,5‐dioxonaphtho[1,2‐d]imidazole‐3‐carboxylic acid phenyl amide ( 4 ), 6‐chloro‐8‐phenylamino‐9H‐7,9,11‐triaza‐cyclohepta[a]naphthalene‐5,10‐dione ( 5 ) and 4‐dimethyl‐amino‐5,10‐dioxo‐2‐phenylimino‐5,10‐dihydro‐2H‐benzo[g]quinazoline‐1‐carboxylic acid amide ( 6 ) were obtained. While on reacting 1 with 2‐guanidinebenzimidazole (GBI) ( 3 ) the products are 3‐(1H‐benzoimidazol‐2‐yl)‐4‐chloro‐3H‐naphtho[1,2‐d]imidazole‐2,5‐dione ( 7 ) and 3‐[3‐(1H‐benzoimidazol‐2‐yl)‐ureido]‐1,4‐dioxo‐1,4‐dihydronaphthalene‐2‐carboxylic acid dimethylamide ( 8 ). 相似文献
4.
A series of π‐conjugated polymers and copolymers containing 1,4‐dioxo‐3,6‐diphenylpyrrolo[3,4‐c]pyrrole (also known as 2,5‐dihydro‐3,6‐diphenylpyrrolo[3,4‐c]pyrrole‐1,4‐dione) (DPP) and 1,4‐phenylene units in the main chain is described. The polymers are synthesised using the palladium‐catalysed aryl‐aryl coupling reaction (Suzuki coupling) of 2,5‐dihexylbenzene‐1,4‐diboronic acid with 1,4‐dioxo‐2,5‐dihexyl‐3,6‐di(4‐bromophenyl)pyrrolo[3,4‐c]pyrrole and 1,4‐dibromo‐2,5‐dihexylbenzene in different molar ratios. Soluble hairy rod‐type polymers with molecular weights up to 21 000 are obtained. Polymer solutions in common organic solvents such as chloroform or xylene are of orange colour (λmax = 488 nm) and show strong photoluminescence (λmax = 544 nm). The photochemical stability is found to be higher than for corresponding saturated polymers containing isolated DPP units in the main chain. Good solubility and processability into thin films render the compounds suitable for electronic applications. 相似文献
5.
《Journal of heterocyclic chemistry》2018,55(7):1554-1563
The reaction of compound 2‐amino‐3‐cyano‐6‐methylquinoxaline‐1,4‐dioxide with cyclohexanone and dimedone in dimethylformamide in the presence of anhydrous ZnCl2 under Friedländer‐type cyclocondensation gave compounds 12‐amino‐9‐methyl‐1,2,3,4,12,12a‐hexahydroquinolino[2,3‐b]quinoxaline‐6,11‐dioxide ( 4 ), 7‐methyl‐4‐oxo‐3,4‐dihydro‐1H‐spiro[benzo[g]pteridine‐2,1′‐cyclohexane]5,10‐dioxide ( 5 ), and 12‐amino‐3,3,9‐trimethyl‐1‐oxo‐1,2,3,4,12,12a‐hexahydroquinolino[2,3‐b]quinoxaline‐6,11‐dioxide ( 6 ); (R)‐3′,3′,7‐trimethyl‐4,5′‐dioxo‐3,4‐dihydro‐1H‐spiro[benzo[g]pteridine‐2,1′‐cyclohexane]5,10‐dioxide ( 7 ) were achieved and evaluated their biological activity as antibacterial and antifungal activities and antitumor evaluation, and also, the density functional theory calculations were evaluated. 相似文献
6.
The reaction of 3‐(1,4‐dioxo‐3,4‐dihydrophthalazin‐2(1H)‐yl)‐3‐oxopropanenitrile 1 and salicyladehyde furnished coumarin derivatives 4 and 5 . Coupling reaction of 1 with aryl diazonium chlorides and benzene‐1,4‐bis (diazonium) chloride gave the corresponding hydrazones 6a , b and bishydrazone 9 , respectively. Hydrazones 6 underwent intramolecular cyclization upon treating with hydrazine hydrate to give 3‐aminopyrazoles 7 . Pyranyl phthalazine 13 was prepared from the reaction of 1 with ethyl 2‐cyano‐3‐ethoxyacrylate 10 . Enaminonitrile 14 was reacted with hydrazine hydrate/phenylhydrazine and hydroxylamine to afford the corresponding pyrazoles 16 and oxime 17 . The antimicrobial evaluation revealed pyrazole derivatives 7a , b and 16a , b displayed a broad spectrum activity against most strains. 3‐Aminopyrazole derivative 7b showed potent antibacterial activity against all tested microorganisms. 相似文献
7.
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
8.
Yoshihisa Kurasawa Ayaka Kawase Jun Takizawa Yuka Maesaki Eisuke Kaji Yoshihisa Okamoto Ho Sik Kim 《Journal of heterocyclic chemistry》2005,42(4):551-556
The 3‐amino‐1‐methylpyridazino[3,4‐b]quinoxalin‐4(1H)‐one 6 and N‐(1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxalin‐3‐yl)carbamates 17a,b were synthesized from the 1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxa‐line‐3‐carboxylate 1b via the 1,5‐dihydro‐4‐hydroxy‐1‐methylpyridazino[3,4‐b]quinoxaline‐3‐carbohydrazide 13b and then 1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxaline‐3‐carboxazide 8 . Heating of compound 13b and arylalde‐hydes afforded the 1,4‐dihydro‐1‐methyl‐4‐oxopyridazino[3,4‐b]quinoxaline‐3‐carbo(2‐arylmethylene)hydrazides 14a‐d. 相似文献
9.
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
10.
ZnII‐ and AuI‐Catalyzed Regioselective Hydrative Oxidations of 3‐En‐1‐ynes with Selectfluor: Realization of 1,4‐Dioxo and 1,4‐Oxohydroxy Functionalizations
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Dr. Appaso Mahadev Jadhav Sagar Ashok Gawade Dr. Dhananjayan Vasu Dr. Ramesh B. Dateer Prof. Dr. Rai‐Shung Liu 《Chemistry (Weinheim an der Bergstrasse, Germany)》2014,20(7):1813-1817
Catalytic 1,4‐dioxo functionalizations of 3‐en‐1‐ynes to (Z)‐ and (E)‐2‐en‐1,4‐dicarbonyl compounds are described. This regioselective difunctionalization was achieved in one‐pot operation through initial alkyne hydration followed by in situ Selectfluor oxidation. The presence of pyridine alters the reaction chemoselectivity to give 4‐hydroxy‐2‐en‐1‐carbonyl products instead. A cooperative action of pyridine and ZnII assists the hydrolysis of key oxonium intermediate. 相似文献
11.
Stanislas Mayer Axelle Arrault GRald Guillaumet Jean‐Yves Mrour 《Journal of heterocyclic chemistry》2001,38(1):221-225
Ethyl 3,4‐dihydro‐2H‐1,4‐benzoxazine‐3‐carboxylate derivatives 2 were obtained and isolated in low yields from the condensation of 2‐aminophenol and ethyl 2,3‐dibromopropanoate. They can be obtained by hydrogenation of ethyl 2H‐1,4‐benzoxazine‐3‐carboxylate in satisfactory yield. Using 2‐iminophenol did not direct the condensation with ethyl 2,3‐dibromopropanoate towards 2 but was fruitfull for the preparation of ethyl 2‐(4‐benzyl‐3,4‐dihydro‐2H‐1,4‐benzoxazin‐3‐yl)acetate from ethyl bromocrotonate. 相似文献
12.
The syntheses of two 2′,3′‐fused bicyclic nucleoside analogues, i.e., 1‐[(4aR,5R,7R,7aS)‐hexahydro‐5‐(hydroxymethyl)‐4,4‐dioxidofuro[3,4‐b][1,4]oxathiin‐7‐yl]pyrimidine‐2,4(1H,3H)‐dione ( 1a ) and 1‐[(4aS,5R,7R,7aS)‐hexahydro‐7‐(hydroxymethyl)‐1,1‐dioxido‐2H‐furo[3,4‐b][1,4]thiazin‐5‐yl]pyrimidine‐ 2,4(1H,3H)‐dione ( 1b ), are described, the key step being an intramolecular hetero‐Michael addition. Their structures and conformations, previously solved by X‐ray crystallography, were analyzed in more detail, using 1D‐ and 2D‐NMR as well as HR‐MS analyses. 相似文献
13.
Taisei Ueda Wataru Doi Shin‐Ichi Nagai Jinsaku Sakakibara 《Journal of heterocyclic chemistry》2000,37(5):1269-1272
Novel heterocycles [1,2,5]selenadiazolo[3,4‐e][1,4]diazepines 3a‐c , [1,2,5]thiadiazolo[3,4‐e]‐[1,4]diazepines 7a‐c , [1,2,5]selenadiazolo[3,4‐e][1,4]oxaepines 4a,b , [1,2,5]thiadiazolo[3,4‐e]‐[1,4]oxazepines 9a‐c and [1,2,5]selena(or thia)diazolo[3,4‐c][1,2,6]thiadiazines 10a,b were synthesized starting form 4,6‐dimethyl[1,2,5]se]enadiazolo[3,4‐d]pyrimidine‐5,7(4H,6H)‐dione 1 or 4,6‐dimethyl‐[1,2,5]thiadiazolo[3,4‐d]pyrimidine‐5,7(4H,6H)‐dione 5 . 相似文献
14.
A series of 6′‐chloro‐1′,1′‐dioxo‐2′H‐spiro[benzo[d][1,3,7]oxadiazocine‐4,3′‐(1,4,2‐benzodithiazine)]‐2,6(1H,5H)‐dione derivatives 2a , 2b and 3a , 3b have been synthesized starting from 3‐aminobenzodithiazines 1a , 1b and isatoic anhydride. Subsequent reactions of 2a with 3‐chlorophenyl isocyanate gave condensation products 4 and 5 . Compound 2a was also converted into 3‐(2‐aminobenzamido)‐6‐chloro‐7‐methyl‐1,1‐dioxo‐1,4,2‐benzodithiazine derivatives 6 , 7 , 8 , 9 , 10 . The mechanisms of the reactions are discussed. 相似文献
15.
Li‐Chai Chen I‐Li Chen Chih‐Chiang Huang Chang‐Hui Liao Jhy‐Yih Chen Tai‐Chi Wang 《中国化学会会志》2010,57(6):1331-1340
Some oxime‐containing 3,4‐dihydroquinolin‐2(1H)‐one derivatives were synthesized and evaluated for their antiplatelet and antiproliferative activities. These compounds were synthesized via alkylation of hydroxyl precursors followed by the reaction with NH2OH. The preliminary assays indicated that (Z)‐7‐[2‐(4‐fluorophenyl)‐2‐(hydroxyimino)ethoxy]‐3,4‐dihydroquinolin‐2(1H)‐one (13c) is the most active against U46619 induced platelet aggregation with an IC50 value of 3.51 μM. For the inhibition of AA‐induced aggregation, (E)‐6‐[2‐(hydroxyimino)propoxy]‐3,4‐dihydroquinolin‐2(1H)‐one (15 ) is the most potent with an IC50 value of 1.85 μM. These oxime‐containing 3,4‐dihydroquinolin‐2(1H)‐one derivatives were inactive against thrombin induced platelet aggregation with an IC50 value of greater than 26.78 μM. For the antiproliferative activity, most of these oxime‐containing 3,4‐dihydroquinolin‐2(1H)‐one derivatives were inactive while (Z)‐7‐[2‐(hydroxyimino)‐2‐(naphthalen‐2‐yl)ethoxy]‐3,4‐dihydroquinolin‐2(1H)‐one (13a) exhibited only marginal activities with GI50 value of 7.63, 7.34 and 6.36 μM against the growth of NPC‐TW01, NCI‐H661, and Jurkat respectively. 相似文献
16.
Daniel E. Vicentes Andrea L. Romero Ricuarte Rodríguez Justo Cobo Christopher Glidewell 《Acta Crystallographica. Section C, Structural Chemistry》2020,76(5):446-453
An efficient synthesis of 1‐arylisochromeno[3,4‐d][1,2,3]triazol‐5(1H)‐ones, involving the diazotization of 3‐amino‐4‐arylamino‐1H‐isochromen‐1‐ones in weakly acidic solution, has been developed and the spectroscopic characterization and crystal structures of four examples are reported. The molecules of 1‐phenylisochromeno[3,4‐d][1,2,3]triazol‐5(1H)‐one, C15H9N3O2, (I), are linked into sheets by a combination of C—H…N and C—H…O hydrogen bonds, while the structures of 1‐(2‐methylphenyl)isochromeno[3,4‐d][1,2,3]triazol‐5(1H)‐one, C16H11N3O2, (II), and 1‐(3‐chlorophenyl)isochromeno[3,4‐d][1,2,3]triazol‐5(1H)‐one, C15H8ClN3O2, (III), each contain just one hydrogen bond which links the molecules into simple chains, which are further linked into sheets by π‐stacking interactions in (II) but not in (III). In the structure of 1‐(4‐chlorophenyl)isochromeno[3,4‐d][1,2,3]triazol‐5(1H)‐one, (IV), isomeric with (III), a combination of C—H…O and C—H…π(arene) hydrogen bonds links the molecules into sheets. When compound (II) was exposed to a strong acid in methanol, quantitative conversion occurred to give the ring‐opened transesterification product methyl 2‐[4‐hydroxy‐1‐(2‐methylphenyl)‐1H‐1,2,3‐triazol‐5‐yl]benzoate, C17H15N3O3, (V), where the molecules are linked by paired O—H…O hydrogen bonds to form centrosymmetric dimers. 相似文献
17.
Substituted 2‐(benzylamino)‐2H‐1,4‐benzoxazin‐3(4H)‐ones are unstable under alkaline and acidic conditions, undergoing opening of the benzoxazinone ring. 2‐Bromo‐2H‐1,4‐benzoxazin‐3(4H)‐ones show similar degradation under alkaline conditions, while replacement of Br at C(2) to give 2‐hydroxy‐2H‐1,4‐benzoxazin‐3(4H)‐ones was observed only under mild alkaline conditions. Mechanisms of ring opening and degradation to 2‐aminophenol derivatives are proposed. 相似文献
18.
A simple and efficient synthesis of 4‐aryl‐3‐methyl‐1‐phenyl‐1H‐benzo[h]pyrazolo[3,4‐b]quinoline‐5,10‐diones has been accomplished by the one‐pot condensation reaction of 3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine, aldehydes and 2‐hydroxynaphthalene‐1,4‐dione in water in the presence of diammonium hydrogen phosphate. 相似文献
19.
Kamal M. El‐Shaieb 《中国化学会会志》2008,55(5):1150-1155
1‐(Dicyanomethylene)acenaphthene‐2‐one ( 1 ) reacts with 1,8‐diaminonaphthalene ( 2 ) to yield two products, identified as acenaphtho[1,2‐b]naphtho[1,8‐ef][1,4]diazepine ( 3 ) and (Z)‐2‐(8‐aminonaphthalen‐1‐ylamino)‐2‐(2‐oxoacenaphthylen‐1(2H)‐ylidene)acetonitrile ( 4 ). On the other hand, (2Z,2′Z)‐2,2′‐(hydrazine‐1,2‐diylidene)diacenaphthylen‐1(2H)‐one ( 6 ) was obtained during the condensation process of 1 with hydrazine hydrate ( 5 ). Reaction of 1 with 3,4‐diaminotoluene ( 8b ) produces 9‐methylacenaphtho[1,2‐b]quinoxaline ( 9b ) and (Z)‐2‐(2‐amino‐5‐methylphenyl‐amino)‐2‐(2‐oxoacenaphthylen‐1(2H)‐ylidene)acetonitrile ( 10b ). However, treatment of 5,6‐diamino‐pyrimidine‐2,4‐diol hemisulphate ( 11 ) with 1 affords acenaphtho[1,2‐g]pteridine‐9,11‐diol ( 12 ). 相似文献
20.
An Approach to the Synthesis of Spiro[indene‐pyridoisoquinoline] Derivatives via 1,4‐Dipolar Cycloaddition of Isoquinoline and Acetylene Esters,and (1,3‐Dihydro‐1,3‐dioxo‐2H‐inden‐2‐ylidene)malononitrile
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Abdolali Alizadeh Vahideh Sadeghi Fahimeh Bayat Long‐Guan Zhu 《Helvetica chimica acta》2014,97(10):1383-1387
A concise and efficient approach to the spiro‐tetrahydroisoquinoline derivatives has been developed by 1,4‐dipolar cycloaddition of zwitterions resulting from isoquinoline and acetylene esters and (1,3‐dihydro‐1,3‐dioxo‐2H‐inden‐2‐ylidene)malononitrile in MeCN at room temperature. The significance of this method lies in good yields and ease of product purification, and no inert atmosphere is required. The structures of the products were confirmed spectroscopically (IR, 1H‐ and 13C‐NMR, and EI‐MS) and by elemental analyses. A plausible mechanism for this reaction is proposed (Scheme). 相似文献