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1.
Bromine-containing organozinc compounds generated from 1,1-dibromo-3,3-dimethylbutan-2-one reacted with 2-arylmethylideneindan-1,3-diones and 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones to give 3-aryl-2-(2,2-dimethylpropanoyl)spiro[cyclopropane-1,2′-indan]-1′,3′-diones and 1-aryl-6,6-dimethyl-2-(2,2-dimethylpropanoyl)-5,7-dioxaspiro[2.5]octan-4,8-diones, respectively. Reactions of 2-arylmethylideneindan-1,3-diones with bromine-containing zinc enolates derived from 1-aryl-2,2-dibromopropan-1-ones and 2,2-dibromo-1,2,3,4-tetrahydronaphthalen-1-one resulted in the formation of 2-aroyl-3-aryl-2-methylspiro-[cyclopropane-1,2′-indan]-1′,3′-diones and 2,3: 8,9-dibenzo-12-phenyldispiro[4.0.5.1]dodecane-1,4,7-trione, respectively.  相似文献   

2.
Mei-Hsiu Shih   《Tetrahedron》2002,58(52):10437-10445
3-Arylsydnone-4-carbohydroximic acid chlorides (1) could react with N-arylmaleimides (3a–b) or 2-methyl-N-phenylmale-imide (3c) to give 3-(3-arylsydnon-4-yl)-5-aryl-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-diones (4a–h) or 6a-methyl-3-(3-arylsydnon-4-yl)-5-phenyl-3a,6a-dihydro-pyrrolo[3,4-d]isoxazole-4,6-diones (4i–l), respectively. However, 3-(arylsydnon-4-yl)-naphtho[2,3-d]isoxazole-4,9-diones (6a–d) were obtained in good yield by the reaction of carbohydroximic acid chlorides 1 with [1,4]naphthoquinone. Furthermore, 2-(3-arylsydnon-4-yl)benzoxazoles (9a–d) and 2-(3-arylsydnon-4-yl)benzothiazoles (9e–h) were obtained via the reaction of carbohydroximic acid chlorides 1 with ortho-substituted aromatic amines 7a and b.  相似文献   

3.
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   

4.
The reaction of 4-oxo-3,4-dihydroquinazolyl-and benzimidazolylacetonitriles with 2-chloro-2-quinolinecarbaldehydes and 1-aryl-5-chloro-3-methyl-1H-pyrazole-4-carbaldehydes gave the corresponding 3-(2-chloro-3-quinolyl)-2-(4-oxo-3,4-dihydro-2-quinazolyl)-2-propenenitriles and 3-(1-aryl-5-chloro-3-methyl-1H-4-pyrazolyl)-2-hetaryl-2-propenenitriles. Intramolecular cyclization of these compounds gives 15-oxo-15H-benzo[6,7][1,8]naphthyridino[2,1-b]quinazoline-6-carbonitriles, 1-aryl-3-methyl-11-oxo-1,11-dihydropyrazolo[4′,3′:5,6]pyrido[2,1-b]quinazoline-5-carbonitriles, and 1-aryl-3-methyl-1H-benzo[4,5]imidazo[1,2-a]pyrazolo[4,3-e]pyridine-5-carbonitriles.  相似文献   

5.
By reaction of 8-substituted 3-bromoacetyl-3,8-dimethyl-2,7-dioxaspiro[4,4]nonane-1,6-diones with thiourea and substituted thioureas under Hansch reaction conditions, we have obtained the novel heterocycles 3-[2′-amino(arylamino)thiazol-4-yl]-3,8-dimethyl-2,7-dioxaspiro[4,4]nonane-1,6-diones. By reacting the above-indicated bromoacetyl spirodilactones with 5-aryl-3-mercapto-1,2,4-triazoles, we obtained 8-substituted 3-(aryl-3,8-dimethyl-1′,2′,4′-triazol-3′-yl)thioacetyl-2,7-dioxaspiro[4,4]nonane-1,6-diones. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 123–129, January, 2006.  相似文献   

6.
1-Ethyl-3-aryl-5-methylpyrazolo[3,4-d]pyrimidine-4,6-diones are formed in small amounts, together with the expected hydrazones, in the reaction of 3-methyl-6-(1-ethylhydrazino)uracil with aromatic aldehydes in ethanol The yield of these diones increases substantially when the reaction is carried out in acetic acid and sodium nitrite is subsequently added to the mixture. A change in the temperature conditions makes it possible to direct this reaction toward the formation of 1-ethyl-3-aryl-6-methylpyrimido[5,7-e]as-triazine-5,7-diones.For Communication 8, see [1].Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 219–224, February, 1992.  相似文献   

7.
1,3-Dipolar cycloaddition of nitrile oxides generated in situ in the presence of variously substituted N-arylmaleimides and N-benzylmaleimide provides new pyrrolo[3,4-d]izoxazoline-4,6-diones in good yields. The whole procedure could be performed in a practical and efficient one-pot operation. All the cycloadducts were isolated in excellent yields and identified by spectral studies. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 444–448, March, 2009.  相似文献   

8.
Cyclocondensation of 5-methylpyrazol-3-amine with methyl cinnamate and arylmethylidenemalonic acids in DMF and methanol leads to the formation of 7-aryl-2-methyl-6,7-dihydropyrazolo[1,5-a]-pyrimidin-5(4H)-ones. Arylmethylidenemalonic acids react with the title amine at a ratio of 1:2 in nitrobenzene to give 4-aryl-3,5-dimethyl-1,7-dihydrodipyrazolo[3,4-b:4′,3′-e]pyridines. Heterocyclizations of 5-methylpyrazol-3-amine with 5-arylmethylidene-2,2-dimethyl-1,3-dioxane-4,6-diones or their precursors, para-substituted benzaldehydes and 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum’s acid) in all solvents (methanol, DMF, and nitrobenzene) give the corresponding 4-aryl-3-methyl-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-ones. The structure of 3-methyl-4-(4-nitrophenyl)-2,4,5,7-tetrahydropyrazolo[3,4-b]pyridin-6-one was proved by X-ray analysis.  相似文献   

9.
5-Phenyl-4-ethoxycarbonyl-1H-pyrrole-2,3-diones react with acetonitriles and dimedone to form ethyl 2-amino-7,7-dimethyl-2′,5-dioxo-5′-phenyl-1′,2′,5,6,7,8-hexahydrospiro[chromene-4,3′-pyrrole]-4′-carboxylates. The crystal and molecular structure of ethyl 2-amino-1′-benzyl-7,7-dimethyl-2′,5-dioxo-5′-phenyl-3-cyano-1′,2′,5,6,7,8-hexahydrospiro[chromene-4,3′-pyrrole]-4′-carboxylate was proved by XRD analysis.  相似文献   

10.
The title compound(4aR,7aS)-6-benzyl-1-((R)-2-(2-chlorophenyl)-4,5-dihydrothiazole-4-carbonyl)-hexahydro-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione(C24H22ClN3O3S)w...  相似文献   

11.
The [3+2] cycloaddition reactions of a series of 1,3-substituted 5-diazo-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindazoles with maleic anhydride and dimethyl acetylenedicarboxylate gave 1′,3′-substituted 3-spiro[4,6-dioxo-4,6,3a,6a-tetrahydro-3H-furo[3,4-c]pyrazole]-5′-[6′,6′-dimethyl-4′-oxo-4′,5′,6′,7′-tetrahydroindazoles] and 1′,3′-substituted 3-spiro[4,5-di(methoxycarbonyl)-3H-pyrazole]-5′-[6′,6′-dimethyl-4′-oxo-4′,5′,6′,7′-tetrahydroindazoles] respectively. When heated the former eliminate nitrogen and are transformed into 1′,3′-substituted 6-spiro[2,4-dioxo-3-oxabicyclo[3.1.0]hexane]-5′-[6′,6′-dimethyl-4′-oxo-4′,5′,6′,7′-tetrahydroindazoles]. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 12, pp. 1784–1791, December, 2007.  相似文献   

12.
4-Acetyl-1-alkoxyaryl-5-aryl-3-hydroxy-2,5-dihydro-1H-pyrrol-2-ones reacted with amines to give 1-alkoxyaryl-5-aryl-4-(1-R-aminoethylidene)pyrrolidine-2,3-diones. Reactions of amines with 4-benzoyl-substituted analogs involve nucleophilic attack on the C3 atom in the heteroring to produce the corresponding 3-R-amino-1-alkoxyaryl-5-aryl-4-benzoyl-2,5-dihydro-1H-pyrrol-2-ones. Reactions of the title compounds with hydrazine hydrate, regardless on the substituent on C4, afforded 4-aryl-3-methyl(phenyl)-5-[2(4)-methoxyphenyl]-4,6-dihydropyrrolo[3,4-c]pyrazol-6-ones.  相似文献   

13.
3-Benzoyl-3a,4,6,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxide is formed as a result of intramolecular cyclization of cis-4-benzamido-3-chlorosulfitothiophan. Only one sulfur atom — that of the sulfoxide group — is removed from the cyclization product and the analogous 3-methoxycarbonyl-3a,4,6,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxide by the action of Raney nickel; the products in this case are, respectively, cis-4-benzamido-3-hydroxythiophan and 3a,4,6,6a-tetrahydrothieno]3,4-d]oxazolidone. The three-dimensional structure of 3-acyl-3a,4,4,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxide was determined by 1H and 13C NMR spectroscopy. A difference between the conformational state of 3-substituted 3a,4,6,6a-tetrahydrothieno[3,4-d][1,2,3]oxathiazoline 2-oxides and 3-substituted 3a,4,6,6a-tetrahydrothieno[3,4-d]oxazolidones was established.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 191–197, February, 1977.  相似文献   

14.
Organozinc compounds prepared from dialkyl dibromomalonates and zinc react with 2-arylmethyl-eneindan-4,6-diones, 5-arylmethylene-2,2-dimethyl-1,3-dioxane-4,6-diones, as well as with 2-[4-(1,3-dioxoindan-2-ylidenemethyl)phenyl]methyleneindan-1,3-dione and 5-[4-(2,2-dimethyl-4,6-dioxo-1,3-dioxane-2-ylidenemethyl)phenyl]methylene-2,2-dimethyl-1,3-dioxane-4,6-diones to form dialkyl 3-aryl-1′3′-dioxaspiro(cyclopropane-2,2′-indan)-1,1-dicarboxylates, dimethyl 3-aryl-6,6-dimethyl-5,7-dioxa-4,8-dioxaspiro[2,5]octan-2,2-dicarboxylates, dialkyl 2-{4-[3,3-bis (alkoxycarbonyl)-1′,3′-dioxaspiro(cyclopropane-2,2′-indan)-1-yl]phenyl}-1′,3′-dioxaspiro[cyclopropane-2,2′-indan]-1,1-dicarboxylates, and dialkyl 2-{4-[2,2-bis(alkoxycarbonyl)-6,6′-dimethyl-4,8-dioxo-5,7-dioxaspiro[2,5]oct-1-yl]phenyl}-6,6-dimethyl-4,8-dioxo-5,7-dioxaspiro[2,5]octan-1,1-dicarboxylate respectively.  相似文献   

15.
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   

16.
Three-component cyclization of 4-aryl-1,4-dihydrobenzo[4,5]imidazo[1,2-a][1,3,5]triazin-2-amines with formaldehyde and primary amines gave the corresponding 6-unsubstituted or 6-aryl-2-alkyl-2,3,4,6-tetrahydro-1H-[1,3,5]triazino[1′,2′:3,4][1,3,5]triazino[1,2-a]benzimidazoles.  相似文献   

17.
Tetrahydrospiropyrrolo[2,1-a]phthalazines were synthesized by the reaction of 5-arylidene-2-spirocyclohexane-1,3-dioxane-4,6-diones with phthalazinium ylides. One of the reaction products, viz., 3-ethoxycarbonyl-2-(4-methoxyphenyl)-2′,2′-pentamethylene-1,2,3,10b-tetrahydrospiro[pyrrolo[2,1-a]phthalazine-1,5′-[1,3]dioxane]-4′,6′-dione, was studied by X-ray diffraction. The spectroscopic characteristics of the reaction products are discussed. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 2362–2365, October, 2005.  相似文献   

18.
Methyl 1-aryl-3-benzoyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 6-amino-1,3-dimethylpyrimidine-2,4(1H,3H)-dione to give methyl 11-aryl-12-benzoyl-9-hydroxy-4,6-dimethyl-3,5,10-trioxo-4,6,8,11-tetraazatricyclo[7.2.1.02,7]dodec-2(7)-ene-1-carboxylates which underwent thermal recyclization to 1-aryl-3-benzoyl-4-hydroxy-1′,3′-dimethylspiro[pyrrole-2,5′-pyrrolo[2,3-d]pyrimidine]-2′,4′,5,6′(1H,1′H,3′H,7′H)-tetraones.  相似文献   

19.
The intramolecular electrophilic substitution in 6-functionalized 1,3-dimethyl-1H-pyrrolo[3,4-d]pyrimidine-2,4(3H,6H)-diones was used for the synthesis of pyrimido[4′,5′:3,4]-pyrrolo[1,2-a]quinoxaline-8,10(7H,9H)-dione, pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,2,4]benzo-triazine-8,10(7H,9H)-dione, and 2H-pyrimido[4′,5′:3,4]pyrrolo[1,2-a]indole-2,4,11(1H, 3H)-trione derivatives. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2180–2185, December, 2006.  相似文献   

20.
Methyl 1-bromocyclopentanecarboxylate and methyl 1-bromocyclohexanecarboxylate reacted with zinc and 2-arylmethylidene-2,3-dihydro-1H-inden-1-ones or 2-arylmethylidene-3,4-dihydronaphthalen-1(2H)-ones to give 4′-aryl-4′,5′-dihydro-2′H-spiro[cyclopentane(cyclohexane)-1,3′-indeno[1,2-b]pyran]-2′-ones or 4-aryl-5,6-dihydrospiro[benzo[h]chromene-3,1′-cyclopentane(cyclohexane)]-2(4H)-ones, respectively.  相似文献   

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