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1.
Reaction of (N-alkyl-N-phenyl)ethoxycarbonylacetamides with β-naphthol in the presence of phosphorus oxychloride afforded 1-oxo-3-(N-alkyl-N-phenyl)amino-1H-naphtho[2,1-b]pyrans. These compounds underwent reaction with N,N-dimethylformamide-phosphorus oxychloride at 95° yielding a mixture of 14H-naphtho[1′,2′:5,6]pyrano[2,3-b]quinoline derivatives and 1-oxo-2-formyl-3-(N-alkyl-N-phenyl)amino-9-oxy-1H-phenalene. When the same reaction was performed at 140°, only 14-oxo-14H-naphtho[1′,2′:5,6]pyrano[2,3-b]quinoline was obtained in a very good yield. The structures of such compounds were demonstrated by spectral data and by chemical transformations. On the other hand, the expected formylation in the 2 position was achieved when 1-oxo-3-(N-alkyl-N-benzyl)amino-1H-naphtho[2,1-b]pyrans reacted with N,N-dimethylformamide-phosphorus oxychloride. 相似文献
2.
3.
N-Methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates readily undergo the Mannich reaction with p-phenylenediamines and excess formaldehyde in the absence of a catalyst to form 3,3??-(1,4-phenylene)-bis(8-aryl-6-oxo-3,4,7,8-tetrahydro-2H,6H-pyrido[2,1-b][1,3,5]thiadiazine-9-carbonitriles) in moderate yields (24?C56%). 相似文献
4.
Reaction of 1-oxo-3-dialkylamino-1 H-naphtho[2,1-b]pyrans with N,N-dimethylformamide in the presence of phosphorus oxychloride afforded the corresponding 1-oxo-2-formyl-3-dialkyl-amino-1H-naphtho[2,1-b]pyrans. Condensation of 1-oxo-2-formyl-3-dimethylamino-1H-naphtho[2,1-b]pyran with hydrazine or monosubstituted hydrazines was found to lead to the formation of 8-alkyl(aryl)-1 1-oxo-8H,1 1H-naplitho[1′,2′:5,6] pyrano[2,3-c]pyrazoles through the intermediate hydrazones and subsequent cyclization. The same result was achieved starting from other 3-dialkylamino derivatives but in a lower yield. 相似文献
5.
A. V. Velikorodov A. K. Kuanchalieva E. A. Melent’eva O. L. Titova 《Russian Journal of Organic Chemistry》2011,47(9):1375-1379
Acylation of 2-aminobenzenethiol with methyl chloroformate in pyridine gave dimethyl 2,2′-disulfanediylbis(2,1-phenylene)dicarbamate
instead of expected methyl 2-suylfanylphenylcarbamate. Heating of the product with zinc dust in glacial acetic acid led to
the formation of 1,3-benzothiazol-2(3H)-one. Alkylation of the latter with 1,2-dibromoethane and allyl bromide, as well as acylation with chloroacetyl chloride,
afforded the corresponding 3-substituted derivatives. 3-[3-(Pyridin-2-yl)-4,5-dihydroisoxazol-5-ylmethyl]-1,3-benzothiazol-2(3H)-one was synthesized with high regioselectivity by 1,3-dipolar cycloaddition of 3-allyl-1,3-benzothiazol-2(3H)-one to pyridine-2-carbonitrile oxide generated fromN-hydroxypyridine-2-carboximidoyl chloride hydrochloride by the action of triethylamine. 相似文献
6.
Shelkovnikov V. V. Loskutov V. A. Vasil’ev E. V. Shekleina N. V. Ryabinin V. A. Sinyakov A. N. 《Russian Chemical Bulletin》2011,60(3):561-569
Photochemical activity of a number of cationic thioxanthen-9-one derivatives for the formation of the trityl cation was studied,
which resulted in the selection of compounds suitable for photodetritylation. 10-(4-Heptyloxyphenyl)-9-oxo-2-(N,N,N-triethylammonio)methyl-9H-thioxanthenium bis(hexafluorophosphate) and 2-methyl-, 2-(2-methyl-1-propanoyl-2-tosyl)-, 1-chloro-4-propoxy-, and 2,4-diethyl-10-(4-heptyloxyphenyl)-9-oxo-9H-thioxanthenium hexafluorophosphates were found to be photoactivators of detritylation of 5′-O-(4,4′-dimethoxytrityl)thymidine. The detritylation reaction is the most efficient in dichloromethane. 2,4-Diethyl-10-(4-heptyloxyphenyl)-9-oxo-9H-thioxanthenium hexafluorophosphate was used as a detritylation photoactivator in the oligonucleotide synthesis using an automated
DNA synthesizer. The yield in the elongation step of the oligonucleotide chain was 98%. 相似文献
7.
An approach to the modification of the biologically active compounds, substituted 2-aminothiophenes, with fluorine-containing
five-membered heterocycles is proposed. The reaction of 2-aminothiophenes with methyl trifluoropyruvate yields the corresponding
N-(2-thienyl)imines, their subsequent cyclocondensation with 1,3-N,N-binucleophiles (2-aminothiazoline and benzamidines) furnished 5-oxo-6-trifluoromethyl-2,3,5,6-tetrahydroimidazothiazoles
and 5-oxo-2-phenyl-4-trifluoromethyl-4,5-dihydro-1H-imidazoles. 相似文献
8.
The preparation of 1,4-dihydro-4-oxo-3′-alkylthio-3,4′-diquinolinyl sulfides 3 or 1,4-dihydro-4-oxo-3-(alkylthio)quinolines 4 by acid catalysed hydrolysis of 4-methoxy-3′-alkylthio-3,4′-diquinolinyl sulfides 1 or 4-methoxy-3-(alkylthio)-quinolines 2 is described. The reactions of 4-methoxy-3′-alkylthio-3,4′-diquinolinyl sulfides 1 or 1,4-dihydro-4-oxo-3′-alkylthio-3,4′-diquinolinyl sulfides 3 with phosphoryl chloride in DMF afforded 4-chloro-3′-alkylthio-3,4′-diquinolinyl sulfides 5 . Treatment of the title compounds 1 or 3 with boiling phosphoryl chloride systems:leads to 4-chloro-3-(alkylthio)quinolines 6 and thioquinanthrene but those of alkoxy- or oxo-quinolines 2 or 4 lead to 4-chloro-3-(alkylthio)quinolines 6 . The reactions of N-methyl-4(1H)-quinolinones 3n and 4n with phosphoryl chloride directed to 4-chloro-3-(alkylthio)quinolines 6 were studied as well. 相似文献
9.
The crystal structure of chromone hydrazonium salt (±)-1-hydroxy-1-oxo-3-phenyl-1,3-dihydro-1λ5-2,1-oxaphospholo[4,5-b]-4H-1-benzopyran-4-one (2) and its acid (±)-1-hydroxy-1-oxo-3-phenyl-1,3-dihydro-1λ5-2,1-oxaphospholo[4,5-b]-4H-1-benzopyran-4-one (3) have been solved. Condensed rings are almost planar, the P atom adopts nearly tetragonal geometry. The molecular packing is influenced by inter- and intramolecular contacts, which can be recognized as hydrogen bonds. 相似文献
10.
V. M. Dianov 《Russian Journal of Organic Chemistry》2006,42(7):1028-1030
The reaction of dihydroimidazole-2-thiol with N-(3-chloro-2-oxopropyl)phthalimide gave 2-[3-(4,5-dihydroimidazol-2-ylsulfanyl)-2-oxopropyl]-1,3-dioxo-1H-isoindole which underwent intramolecular heterocyclization to dihydroimidazothiazole system by the action of a dehydrating agent. Treatment of 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazole with concentrated hydrochloric acid led to the formation of dihydroimidazo[2,1-b]thiazol-3-ylmethanamine. Water-soluble quaternary 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazolium salts were obtained by alkylation of 3-(1,3-dioxo-1H-isoindol-2-ylmethyl)-5,6-dihydroimidazo[2,1-b]thiazole with alkyl halides. 相似文献
11.
A. N. Fedotov E. V. Trofimova T. E. Gulov S. G. Bandaev S. S. Mochalov N. S. Zefirov 《Russian Journal of Organic Chemistry》2013,49(10):1534-1541
Sovomercuration adducts of 2-nitrobenzyl-, 2-nitro-4,5-(ethylenedioxy)benzyl-, and 4,5-dimethoxy-2-nitrobenzylcyclopropanes were synthesized. The adducts reacted with sulfuric, fluorosulfonic, or chlorosulfonic acid to give 3-(2-chloromercurio)ethyl-1-oxo-3,4-dihydro-1H-2,1-benzoxazinium ions whose stability depended on the nature of substituents in the aromatic ring. Unstable metalated 1-oxo-3,4-dihydro-1H-2,1-benzoxazinium ions underwent fast protodemercuration to form metal-free 3-ethyl-1-oxo-3,4-dihydro-1H-2,1-benzoxazinium ions. Stable analogs in the above acids did not change to an appreciable extent over a period of 48–72 h. Hydrolysis of stable metalated 1-oxo-1,3-dihydro-2,1-benzoxazolium ions afforded only 4-chloromercurio-1-(2-nitroaryl)butan-2-ol. 相似文献
12.
Ho Sik Kim Tong Eun Kim Sam Tag Kwag Yong Tae Park Young Seuk Hong Yoshihisa Okamoto Yoshihisa Kurasawa 《Journal of heterocyclic chemistry》1997,34(5):1539-1542
The reaction of the 6-chloro-2-(1-methyl-2-thiocarbamoylhydrazino)quinoxaline 4-oxides 3a-d with trifluoroacetic anhydride gave the 2-(N-aryl)trifluoroacetamido-8-chloro-4-methyl-4H-1,3,4-thiadiazino-[5,6-b]quinoxalines 7a-d , respectively, while the reflux of compounds 3a-c in N,N-dimethylformamide afforded the mesoionic triazolo[4,3-a]quinoxaline 4 . Hydrolysis of compounds 7a-d with triethylamine/water provided the 2-arylamino-8-chloro-4-methyl-4H-1,3,4-thiadiazino[5,6-b)]quinoxalines 8a-d , respectively. 相似文献
13.
The thermolysis of (Z)-methyl 3-(6-azido-3-chloro-1-methyl-4-oxo-1,4-dihydropyridazin-5-yl)-2-methylacrylate ( II ) provides a new synthetic route to pyrrolo[2,3-c-]pyridazines, specifically, methyl 3-chloro-1,6-dimethyl-4-oxo-1,4-dihydro-7H-pyrrolo[2,3-c]pyridazine-5-carboxylate ( III ) in 91% yield. Treatment of III with ozone provides an entry into the novel pyridazino[3,4-d][1,3]oxazine ring system, specifically, 3-chloro-1,7-dimethylpyridazino[3,4-d][1,3]oxazine-4,5-dione ( IV ) in 73% yield. Compound IV is smoothly hydrolyzed into 6-acetylamino-3-chloro-1-methyl-4-oxo-1,4-dihydropyridazine-5-carboxylic acid ( V ) which is readily recyclized into IV by dehydration with acetic anhydride. Furthermore, IV undergoes a facile reductive ring opening reaction with sodium borohydride to give 3-chloro-6-ethylamino-1-methyl-4-oxo-1,4-dihydropyridazine-5-carboxylic acid ( VI ) in 95% yield. 相似文献
14.
Reaction of 1-oxo-3-dialkylamino-1H-naphtho[2,1-b]pyrans, 4-hydroxycoumarin and formaldehyde gave rise to the formation of 1-oxo-2-((2-oxo-4′-hydroxy-2′H-1′-benzopyran-3′-yl)-melhyl J-3-dialkylamino-1H-naphtho[2,1-b]pyrans. When these compounds were refluxed in glacial acetic acid, cyclization occurred and 6,8-dioxo-6H,7H,07-,5,15,16-trioxadibenzo[a,j]-naphthacene arose by cleavage of the dialkylamino group. In a similar manner, starting from suitable products, many other trioxanaphthacene or azadioxanaphthacene derivatives were synthesized. 相似文献
15.
Sung Hoon Kim Yong Hoon Ra Yoon Young Lee Kyongtae Kim Joong Hyup Kim 《Journal of heterocyclic chemistry》1994,31(6):1361-1368
The reactions of 1-alkylamino-1-alkylthio-3-phenylpropene-3-thiones 3 with thiophosgene and phosgene in toluene, followed by treatment of the reaction mixture with triethylamine gave 3-alkyl-2,3-dihydro-4-oxo-6-phenyl-2-thioxo- 4 , 3-alkyl-2,3-dihydro-2,4-dioxo-6-phenyl-4H-1,3-thiazines 5 , respectively in good to excellent yields. Similarly treatment of compounds 3 with N-arylimidoyl dichloride in benzene at room temperature gave 3-alkyl-2-arylimino-2,3-dihydro-4-oxo-6-phenyl-4H-1,3-thiazines 6 in excellent yields. The reactions of compounds 3 with oxalyl chloride in toluene gave also 5 in good yields. 相似文献
16.
Reactions of 3-Z-aroylmethylene-6-chloro-3,4-dihydro-2H-1,4-benzoxazine-2-ones with oxalyl chloride afford 3-aroyl-8-chloro-1,2-dihydro-4H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones and Z-3-(2-aryl-2-chlorovinyl)-6-chloro-2H-1,4-benzoxazine-2-ones. Aroyl(imidoyl)ketenes generated by decarbonylation of pyrrolobenzoxazinetriones undergo dimerization through [4+2]-cycloaddition to form 4-aroyl-3-aroyloxy-2-(2-oxo-2H-1,4-benzoxazin-3-yl)-1H, 5H-pyrido[2,1-c][1,4]benzoxazine-1,5-diones. 相似文献
17.
A series of 3,4-Dihydro-2-oxo-(3-substituted-2H-1,3-benzoxazin-4-yl)ureas (II, Table I) and 3,4-dihydro-2-oxo-(3-substituted-2H-1,3-benzoxazin-4-yl)thioureas (Table II) was prepared by treating 3,4-dihydro-4-hydroxy-3-substituted-2H-1,3-benzoxazin-2-ones with ureas and thioureas, respectively. In the presence of alcoholic alkali these compounds underwent transacylation to dihydro-6-(2-hydroxyaryl)-1,3,5-triazine-2,4-(1H,2H)diones (Table III) and their 4-thio analogues (Table IV). 相似文献
18.
Two synthetic pathways for the achievement of the title compounds are reported. The key intermediate, namely 3-carboxy-4-phenyl-2(1H)-quinolinone 9 , was directly cyclized into the corresponding 6-chloro-7H-indeno[2,1-c]quinolin-7-one 10 or alternatively it was esterified, reduced to the alcohol, chlorinated and cyclized into the 6-chloro-7H-indeno[2,1-c]quinoline 8 . Further reaction of the chloroindenoquinoline derivatives with N-methylpiperazine afforded the piperazinyl derivatives 4a-c . 相似文献
19.
The reaction of 2-chloro-4-(methylsulfonyl)benzoyl chloride ( 5 ) with 1-methyl-1H-2,1-benzothiazin-4-(3H)-one 2,2-dioxide ( 4 ) gave the O-benzoyl compound, 1-methyl-2,2-dioxido-1H-2,1-benzothiazin-4-yl 2-chloro-4-(methylsulfonyl)benzoate ( 6 ), which rearranged to give the C-benzoyl isomer, [2-chloro-4-(methylsulfonyl)phenyl] (4-hydroxy-1-mefhyl-2,2-dioxido-1H-2,1-benzothiazin-3-yl)methanone ( 7 ). The O-cinnamoyl compound 13 that resulted from the addition of 2,4-dichlorocinnamoyl chloride ( 11 ) to compound 4 rearranged to give the C-cinnamoyl compound, 3-(2,4-dichlorophenyl)-1-(4-hydroxy-1-methyl-2,2-dioxido-1H-2,1-benzothiazin-3yl)-2-propen-1-one ( 15 ). On the other hand, 1-methyl-2,2-dioxido-1H-2,1-benzothiazin-4-yl 3-phenyl-2-propenoate ( 19 ) (from cinnamoyl chloride ( 17 ) and compound 4 ) rearranged to give 2,3-dihydro-6-methyl-2-phenyl-4H,6H-pyrano[3,2-c][2,1]benzothiazin-4-one 5,5-dioxide ( 21 ), an example of a hitherto unknown ring system. Additional examples of this novel heterocycle were prepared from 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 23 ) and 1-methyl-1H-thieno[3,2-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 8 ). 相似文献
20.
Thermolysis of 3-aroylpyrrolo[1,2-d][1,4]benzoxazine-1,2,4(4H)-triones generates aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes which react as dienes at the aroylketene fragment in [4 + 2]-cycloaddition at the C=N bond of N,N??-dicyclohexylcarbodiimide with formation of 3-[6-aryl-4-oxo-3-cyclohexyl-2-cyclohexylimino-3,4-dihydro-2H-1,3-oxazin-5-yl]-2H-1,4-benzoxazin-2-ones. Thermolysis of the latter is accompanied by elimination of N,N??-dicyclohexylcarbodiimide, and aroyl(2-oxo-1,4-benzoxazin-3-yl)ketenes thus generated undergo cyclodimerization to produce 7-aroyl-6,10-dioxo-9-(2-oxo-2H-1,4-benzoxazin-3-yl)-6,10-dihydrobenzo[b]pyrido[1,2-d][1,4]oxazin-8-yl benzoates. 相似文献