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1.
A preparative procedure for the synthesis of 2-alkyl-1-aryl-1,2-dihydrochromeno[2,3-c]pyrrole-3,9-diones from methyl 4-(o-hydroxyphenyl)-2,4-dioxobutanoate, aromatic aldehyde, and aliphatic amine is described. 相似文献
2.
Vyacheslav Ya Sosnovskikh Boris I UsachevDmitri V Sevenard Gerd-Volker Röschenthaler 《Tetrahedron》2003,59(15):2625-2630
The redox reaction of 2-trifluoromethylchromones with ethyl mercaptoacetate in the presence of triethylamine results in the formation of 1,2-dihydrothieno[2,3-c]chromen-4-ones and diethyl 3,4-dithiadipate in high yields. Oxidation of the first compounds with nitrogen dioxide gave 1,2-dihydrothieno[2,3-c]chromen-3,4-diones which were converted into thieno[2,3-c]chromen-4-ones. 相似文献
3.
Shunsaku Shiotani Youichi Tsukamoto Yasuyuki Kitagawa 《Journal of heterocyclic chemistry》1997,34(1):129-141
Furo[3,2-c]-( 1a ), -[2,3-c]- ( 1b ) and -[3,2-b]pyridine ( 1c ) were reacted with isopropyl chloroformate and trimethyl phosphite to give dimethyl 5-isopropoxycarbonyl-4,5-dihydrofuro[3,2-c]pyridine-4-phosphonate ( 2a ), dimethyl 6-isopropoxycarbonyl-6,7-dihydrofuro[2,3-c]pyridine-7-phosphonate ( 2b ) and dimethyl 4-isopropoxycarbonyl-4,7-dihydrofuro[3,2-b]pyridine-7-phosphonate ( 2c ) as unstable syrups. Reaction of 2b and 2c with n-butyllithium and then with benzaldehyde, p-methoxybenzaldehyde, p-cyanobenzalde-hyde or propionaldehyde afforded the normal Wittig reaction products 5b-H, 5b-OMe, 5b-CN, 5b-Et, 5c-H, 5c-H, 5c-OMe and 5c-CN , except for 2b with propionaldehyde. While, the same reactions of compound 2a and the reaction of 2b with propionaldehyde afforded the unexpected products, 5-isopropoxycar-bonylfuro[3,2-c]pyridinio-4-aryl-(or ethyl)methoxides 3a-H, 3a-OMe, 3a-CN and 3a-Et , 4-(1′-aryl(or ethyl)-1′-hydroxymethyl)furo[3,2-c]pyridines 4a-H, 4a-OMe, 4a-CN and 4a-Et accompanying formation of the normal products. Treatment of the normal Wittig reaction products with lithium diisopropylamide and then with acetone gave the derivatives alkylated at the 2-or the benzylic positions. 相似文献
4.
Treatment of ethyl 4-aryl-6-(trifluoromethyl)-2-oxo-2H-pyran-3-carboxylates, prepared from 4,4,4-trifluorobutane-1,3-diones, PCl5 and sodium diethyl malonate, with sulfuric acid afforded the intramolecular Friedel–Crafts acylation products, 3-(trifluoromethyl)indeno[2,1-c]pyran-1,9-diones, from which 2-(trifluoromethyl)-6H-pyrano[3,4-c]quinoline-4,5-diones were obtained via the Schmidt reaction in moderate yields. The latter reacted with sodium azide to give 2-oxo-4-(5-trifluoromethyl-1,2,3-triazol-4-yl)-1,2-dihydroquinoline-3-carboxylic acids in good yields. 相似文献
5.
Starting from the readily available 2-aminobenzhydrols ( 7 ), 3-amino-1,2,4-benzotriazine ( 11 ) and 2-amino-3-pyridinol ( 12 ), novel derivatives of 5-phenyl-5H-imidazo[1,2-a][3,1]benzothiazine-2-carboxylic acid, ethyl ester ( 4 ), imidazo[2,1-c][1,2,4]benzotriazine-2-carboxylic acid, ethyl ester ( 5 ) and 4H-imidazo[2,3-c]pyrido-[2,3-e][1,4]oxazine ( 6 ) were prepared. 相似文献
6.
The synthesis of 5,8-difluoronaphtho[2,3-c]thiophene-4,9-dione ( 2a ) has been accomplished. Treatment of 2a with 2,2-dimethylaminoethylamine leads to 2-[2-(dimethylamino)ethyl]-5-[2-(dimethylamino)ethylamino]-8-fluoronaphtho[2,3-c]pyrrole-4,9-dione ( 6 ). 相似文献
7.
Mohamed I. Ali Abou El-fotooh G. Hamman Salwa F. Mohamed 《Phosphorus, sulfur, and silicon and the related elements》2013,188(3-4):211-216
Abstract 1,2,3,4-Tetrahydro-l-aryl-3,9-dioxo-2,4-diazafluorenes (2) and 1,2,3,4-tetrahydro-1-aryl-9-oxo-3-thi-oxo-2,4-diazafluorenes (3) were newly synthesized. Compounds 3 reacted with chloroacetic acid, α-bromopropanoic acid, or B-bromopropanoic acid in the presence of fused sodium acetate and acetic anhydride to give 2,3-dihydro-5-aryl-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (4), 2-methyl-2,3-dihydro-5-aryl-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (5) and 2,3-dihydro-6-aryl-6H,7H-thiazino[3,2-b]2,4-diazafluorene-4,7-diones (6), respectively. 2,3-Dihydro-2-arylmethylene-5-aryl-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (7) were prepared by the reaction of compounds (3) with chloroacetic acid and aromatic aldehydes in the presence of fused sodium acetate and acetic anhydride or by the reactions of (4) with aromatic aldehydes in the presence of acetic anhydride. 2-(Arylhydroazono)-5-aryl-2,3-dihydro-5H,6H-thiazolo[3,2-b]2,4-diazafluorene-3,6-diones (8) were synthesized by coupling (4) with aryldiazonium salts in the presence of pyridine. 相似文献
8.
V. V. Shchepin P. S. Silaichev R. V. Shchepin M. A. Ezhikova M. I. Kodess 《Russian Journal of Organic Chemistry》2005,41(4):527-534
Zinc enolates derived from 1-aryl-2,2-dibromoalkanones react with N-cyclohexyl-2-oxochromene-3-carboxamides to give N-cyclohexyl-1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides mainly as cis isomers with respect to the substituents in positions 1 and 1a. Reactions of the same zinc enolates with N-benzyl-2-oxochromene-3-carboxamide and N-benzyl-6-bromo-2-oxochromene-3-carboxamide lead to formation of 1-aryl-2-benzyl- and 1-aryl-2-benzyl-6-bromo-1-hydroxy-9c-alkyl-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. The reaction of zinc enolates with N-aryl-2-oxochromene-3-carboxamides in a weakly polar solvent (diethyl ether or ethyl acetate) affords mixtures of cis-N-aryl-1-aroyl-1-alkyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides and their cyclic isomers, 9c-alkyl-1,2-diaryl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-azacyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones, the latter prevailing. N-Substituted 1-alkyl-1-aroyl-2-oxo-1a,7b-dihydrocyclopropa[c]chromene-1a-carboxamides in which the aroyl group on C1 and the carboxamide group on C1a are arranged trans are formed by reactions of zinc enolates with the corresponding 2-oxochromene-3-carboxamides in the presence of hexamethylphosphoric triamide.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 539–546.Original Russian Text Copyright © 2005 by V. Shchepin, Silaichev, R. Shchepin, Ezhikova, Kodess. 相似文献
9.
The reaction of zinc enolates synthesized from 1-aryl-2,2-dibromoalkanones and zinc with 6-R-2-oxochromene-3-carboxylic acid N-benzylamide affords 8-R-9c-alkyl-1-aryl-2-benzyl-1-hydroxy-1,2,9b,9c-tetrahydro-5-oxa-2-aza-cyclopenta[2,3]cyclopropa[1,2-a]naphthalene-3,4-diones. Acylation of these compounds is accompanied by an unexpected rearrangement producing a sole geometrical isomer of 4′-alkyl-5′-aryl-1′-benzyl-3,4,2′,3′-tetrahydro-2,2′-dioxospiro[chroman-3,3′-pyrrol]-4-yl acetates. 相似文献
10.
A. Monge V. Martinez-Merino M. A. Simon C. Sanmartin 《Journal of heterocyclic chemistry》1992,29(6):1545-1549
This paper reports the synthesis of new pyrido[2,3-d]pyrimidin-4-one derivatives as diuretic agents. Starting with 1,2-dihydro-5-nitro-2-oxo-3-pyridinecarboxylic acid 1 , ethyl 2-ethoxy-5-nitro-3-pyridincarboxylate 4 was obtained. Compound 4 reacts with ammonia, methylamine or S-methylpseudothiourea to give the respective 2-amino-5-nitro-3-pyridinecarboxamide derivatives 5 and 6 or 2-methylthio-6-nitro-3H-pyrido[2,3-d]pyrimidin-4-one 8. Treating carboxamide 5 with arylaldehydes and zinc dichloride, new 2-aryl-1,2-dihydro-6-nitro-3H-pyrido[2,3-d]pyrimidin-4-ones 9 were synthetised. These compounds reduced with iron(II) hydroxide gave 6-amino-2-aryl-1,2-dihydro-3H-pyrido[2,3-d]pyrimidin-4-ones 10 as expected. 相似文献
11.
The Synthesis of 2,3,4,5-1H-Tetrahydroimidazo[2,1-b]quinazolin-2,5-diones and analogous 2,3,4,5-1H-Tetrahydroimidazo[1,2-a]thieno[2,3-d] (or [3,2-d])-pyrimidin-2,5-diones The syntheses of various imidazo [2, 1-b]quinazolinediones and their thiophene analogs are described. 相似文献
12.
Rodinovskaya L. A. Gromova A. V. Shestopalov A. M. Nesterov V. N. 《Russian Chemical Bulletin》2003,52(10):2207-2213
Substituted 3-hydroxypyrazoles, which were prepared based on ethyl esters of substituted 4-(pyridin-2-ylthio)- or 4-(1,4-dihydropyridin-2-ylthio)acetoacetic acids and hydrazine hydrate, were used in the synthesis of 6-amino-4-aryl-5-cyano-3-(pyridin-2-ylthiomethyl)-2,4-dihydropyrano[2,3-c]pyrazoles. The molecular and crystal structure of 6-amino-5-cyano-3-(3-cyano-4,6-dimethylpyridin-2-ylthiomethyl)-4-(2-nitrophenyl)-2,4-dihydropyrano[2,3-c]pyrazole was established by X-ray diffraction analysis. 相似文献
13.
Gulnaz F. Krainova Yulia O. Chudinova Alexey A. Gorbunov Olga A. Mayorova Vladimir A. Glushkov 《Mendeleev Communications》2012,22(4):201-202
The Povarov-type condensation of ethyl 2-(arylimino)acetates, 1-aryl-2-aryliminoethanones or N-benzylideneanilines with benzo[b]-furan affords 5,6,6a,11b-tetrahydrobenzofuro[2,3-c]quinolines and/or related benzofuro[2,3-c]quinolines. 相似文献
14.
The previously unknown polycyclic heterocyclic ring systems, namely, [1]benzothieno[2,3-c]naphtho[1,2-h]-quinoline and [1]benzothieno[2,3-c]naphtho[1,2-h][1,2,4]triazolo[4,3-a]quinoline were synthesized via photocyclization of 3-chloro-N-(1′-phenanthryl)benzo[b]thiophene-2-carboxamide. 相似文献
15.
Christian Deshayes Bernard Pujol Suzanne Gelin 《Journal of heterocyclic chemistry》1986,23(5):1415-1418
Some 5-aryl-4,5-dihydro[1]benzoxepin-3(2H)-ones and 5-aryl-5,6,8,9-tetrahydro-7H-benzocyclohepten-7-ones were synthesized by hydrogenolytic cleavage of the isoxazole ring of 4-aryl-3-oxo-3,3a,4,10-tetrahydro[1]-benzoxepino[3,4-c]isoxazoles or 4-aryl-3-oxo-3a,4,9,10-tetrahydro-3H-benzo[4,5]cyclohepta[1,2-c]isoxazoles which in turn were prepared from ethyl 3-oxo-4-phenoxybutanoate or ethyl 3-oxo-5-phenylpentanoate by simple methods. 相似文献
16.
The reaction of methyl 2-bromo-6-(trifluoromethyl)-3-pyridinecarboxylate ( 1 ) with methanesulfonamide gave methyl 2-[(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridine-carboxylate ( 2 ). Alkylation of compound 2 with methyl iodide followed by cyclization of the resulting methyl 2-[methyl(methylsulfonyl)amino]-6-(trifluoromethyl)-3-pyridinecarboxylate ( 3 ) yielded 1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 4 ). The reaction of compound 4 with α,2,4-trichlorotoluene, methyl bromopropionate, methyl iodide, 3-trifluoromethylphenyl isocyanate, phenyl isocyanate and 2,4-dichloro-5-(2-propynyloxy)phenyl isothiocyanate gave, respectively, 4-[(2,4-dichlorophenyl)methoxy]-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazine 2,2-dioxide ( 5 ), methyl 2-[[1-methyl-2,2-dioxido-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4-yl]oxy]propanoate ( 6 ), 1,3,3-trimethyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2]thiazin-4(3H)-one 2,2-dioxide ( 7 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-[3-(trifluoromethyl)phenyl]-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 8 ), 4-hydroxy-1-methyl-7-(trifluoromethyl)-N-phenyl-1H-pyrido[2,3-c][1,2]thiazine-3-carboxamide 2,2-dioxide ( 9 ) and N-[2,4-dichloro-5-(2-propynyloxy)phenyl]-4-hydroxy-1-methyl-7-(trifluoromethyl)-1H-pyrido[2,3-c][1,2] thiazine-3-carboxamide 2,2-dioxide ( 10 ). 相似文献
17.
Derivatives of the 5H-thiazolo[3,2-b]- and 2H-thiazolo[2,3-c]-as-triazine systems were synthesized via condensation of tetrahydro-I-methyl-as-triazine-3(2H)-thione with ethylene dibromide and ethyl bromoacetate, respectively. An hypothesis is given for the formation of the [3,2-b] system in one of these reactions and the [2,3-c] system in the other. Structure proof was accomplished by an unequivocal synthesis of one of the [2,3-c] derivatives. 相似文献
18.
9,10-Dimethoxy-1,2,3,4,12,13-hexahydro-1-oxoquino[1,2-c]quinazolinium perchlorate, 1,2,3,4,13,24-hexahydro-1-oxo[1,3]dioxolo[4,5-g]quino[1,2-c]quinazolinium perchlorate, 6-methyl-2,3,9,10-tetramethoxyquino-[1,2-c]quinazolinium perchlorate and 2,3-dimethoxy-13-methyl[1,3]dioxolo[4′,5′:6,7]quino[1,2-c]quinazolinium perchlorate were synthesized as analogs of the potent antitumor benzo[c]phenanthridine alkaloids nitidine and fagaronine. The related 2,3,8,9-tetramethoxyindazolo[2,3-a]quinoline and 2,3-dimethoxy[1,3]dioxolo-[4,5-g]indazolo[2,3-a]quinoline were also synthesized. Further, the novel formation of 6,7-dimethoxy-2-(2-ethylamino-4,5-dimethoxyphenyl)quinoline via reductive alkylation with Raney nickel in refluxing ethanol is also reported. 相似文献
19.
The conversion of 2-acylamino-3-amino-1,4-naphthoquinones (II) to the corresponding 2-substituted 1H-naphth[2,3-d]imidazole-4,9-diones (I) under both alkaline and acid catalyzed conditions has been effected and the results compared. Treatment of 3-(4′-chlorobutanonyl-amino)-3-amino-1,4-naphthoquinone (He) with aqueous ethanolic sodium hydroxide solution gives 1,2-butanonaphth[2,3-d]imidazole-4,9-dione (V); whereas, treatment of lie with refluxing formic acid gave 2-(4′-chlorobutyl)-1H-naphth[2,3-d]imidazole-4,9-dione. Treatment of 2-substi-tuted 1H-naphth[2,3-d]imidazole-4,5-diones in DMF with alkyl halides in the presence of potassium carbonate affords the expected 1,2-disubstituted naphth[2,3-d]imidazole-4,9-diones (VI). The spectral properties of I, II, V and VI as well as those of some 2-acylamino-3-chloro-1,4-naphthoquinones IV are discussed. 相似文献
20.
Synthesis of (imidazo[1,2-C]pyrimidin-2-yl)phenylmethanones and 6-benzoylpyrrolo[2,3-D]pyrimidinones
Geoffrey Danswan Peter D. Kennewell W. Roger Tully 《Journal of heterocyclic chemistry》1989,26(2):293-299
4-Pyrimidinamines have been reacted with 3-bromo-1-phenylpropane-1,2-dione to give a series of (imidazo[1,2-c]pyrimidin-2-yl)phenylmethanones. The dione also reacted with ethyl amidinoacetate to yield ethyl 2-amino-5-benzoylpyrrole-2-carboxylate which was used to prepare a series of 6-benzoylpyrrolo[2,3-a]pyrimidines. 相似文献