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1.
Synthesis of 3,3′-(1,6-hexanediyl)bis-pyrimidine derivatives and 3,4-dithia[6.6](1.3)pyrimidinophane
Toshio Kinoshita Shirou Odawara Keiko Fukumura Sunao Furukawa 《Journal of heterocyclic chemistry》1985,22(6):1573-1576
Several 3,3′-(1,6-hexanediyl)bis[6-methyl-2,4(1H,3H)-pyrimidinedione] derivatives ( 4a, 4b , and 4c ) were synthesized from 1,6-(hexanediyl)bis[6-methyl-2H-1,3-oxazine-2,4(3H)-dione] (3) . Compound 4c was converted to 6, which reacted with thiourea giving thiuronium salt 7 . 3,3′-(1,6-Hexanediyl)bis [1-(2-mercaptoethyl)-6-methyl-2,4(1H,3H)-pyrimidinedione] (9) was obtained by the hydrolysis of 7 , and then 9 was oxidized to 12,22-dimethyl-3,4-dithia[6.6] (1.3)-1,2,3,4-tetrahydro-2,4-dioxopyrimidinophane (10) . 相似文献
2.
N. M. Tutynina N. L. Racheva V. A. Maslivets Z. G. Aliev A. N. Maslivets 《Russian Journal of Organic Chemistry》2013,49(1):95-98
3-Aroyl-1H-pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones reacted with 5,5-dimethylcyclohexane-1,3-dione to give 3′-aroyl-4′-hydroxy-1′-(2-hydroxyphenyl)-6,6-dimethyl-6,7-dihydrospiro[1-benzofuran-3,2′-pyrrole]-2,4,5′(1′H,5H)-triones. The crystalline and molecular structures of 3′-benzoyl-4′-hydroxy-1′-(2-hydroxyphenyl)-6,6-dimethyl-6,7-dihydrospiro[1-benzofuran-3,2′-pyrrole]-2,4,5′(1′H,5H)-trione were determined by X-ray analysis. 相似文献
3.
Wen-Ting Zhang Jian Sun Hong Zhu Rui-Xue Yue Yi Zhang Fu-Xiang Niu Liangce Rong 《Journal of heterocyclic chemistry》2020,57(4):1912-1924
We have developed a simple and facil protocol for the synthesis of tetrahydrospiro(indoline-3,11′-pyrazolo[4,3-a]acridine)-2,10′(7′H)-dione, tetrahydrospiro(indoline-3, 11′-pyrazolo[3,4-a]acridine)-2,10′(7′H)-dione, and tetrahydrospiro (indoline-3,11′-pyrrolo[3,2-a]acridine)-2,10′(7′H)-dione via PTSA·H2O-induced cyclization reaction from isatins, dimedone, and 5-aminoindazole (6-aminoindazole or 5-aminoindole) in mixed solvent (EtOH and CH3CN). In this research, 5-aminoindazole, 6-aminoindazole, and 5-aminoindole were effectively used to react with isatins and dimedone to give spiroacridinone derivatives. The advantages of this method are mild conditions, convenient manipulation, high yields, and a wide range of substrates. 相似文献
4.
Karishna C. Joshi Anshu Dandia Sunita Baweja Amitabh Joshi 《Journal of heterocyclic chemistry》1989,26(4):1097-1099
An elegant one-step synthesis of two novel spiro ring systems viz: spiro[3H-indole-3,4′-(2′-amino-3′-carbonitrile-[4′H]-pyrano[3,2-c]benzopyran)]-2,5′(1H)-dione8 and spiro[(2-amino-3-carbonitrile-indeno[1,2-b]pyran)-4(5H)>3′-[3H]indole]-2′,5(1′H)-diones in 80–85% yields is described. The spiro heterocycles were prepared by the reactions of fluorine containing 3-dicyanomethylene-2H-indol-2-ones with 4-hydroxy-2H-1-benzopyran-2-one and 1H-indene-1,3(2H)-dione respectively. The synthesized compounds have been characterized on the basis of elemental analyses, ir, pmr, 19F nmr and mass spectral data. 相似文献
5.
A combinatorial synthesis and evaluation of antibacterial activity against clinically isolated resistant strains of Gram-positive and Gram-negative bacteria of 3′-(phenylamino)-1′H-spiro[indoline-3,2′-quinazoline]-2,4′(3′H)-dione derivatives is described. 相似文献
6.
The spiro[cyclohexane-1,2′-[2H]indene] derivatives 15a , b with molecular dimensions and nucleophilic functional groups similar to known steroid 5α-reductase inhibitors (e.g. 2 ) were synthesized. The spiro[cyclohexane-1,2′-[2H]indene]-1′(3′H),4-dione ( 5 ) was synthesized from 5-methoxyindan-l-one ( = 2,3-dihydro-5-methoxy-1H-inden-1-one). A Grignard reaction and a dehydration step led to the cyclohexene (±)- 7 which, upon a stereoselective hydrogenation catalyzed by Raney-Ni under mild conditions, gave 8a as a pure epimer. Further hydrogenation and hydrogenolysis of 8a over Pd/C at room temperature reduced the keto group to give pure 9a . Finally, the 5′-substituted derivatives 12a , 14a , and 15a were generated by deprotection and Heck-type reaction. 相似文献
7.
Qingqing Niu Junhua Xi Lei Li Li Li Chengli Pan Meijun Lan Liangce Rong 《Tetrahedron letters》2019,60(43):151181
An efficient synthesis of spiro compounds via two different pathways from the reactions of isatins, 3-phenylisoxazol-5(4H)-one (3-ethylisoxazol-5(4H)-one), and pyrazol-5-amine (6-aminopyrimidine-2,4(1H,3H)-dione) were reported. The catalyst Amberlyst-15 could be easy recycled and reused for many time without any appreciable loss in catalytic activity. The new type spiro compounds were gained through the ring-opening of isatins process. The structures of spiro[indoline-3,4′-isoxazolo[5,4-b]pyrazolo[4,3-e]pyridin]-2-one, spiro[isoxazolo[5,4-b]quino line-4,5′-pyrrolo[2,3-d]pyrimidine]-2′,4′,6′(1′H,3′H,7′H)-trione, and spiro[indoline-3,4′-pyrazolo[3,4-b]pyridine]-2,6′(5′H)-dione were successfully confirmed by 1H NMR, 13C NMR, HRMS, and X-ray crystal diffraction analysis. 相似文献
8.
The title compounds have been prepared, by the cyclocondensation of thiolactic acid with isatin-3-imines. 5′-Methyl-3′-phenyl-spiro[3H-indole-3,2′-thiazolidine]-2,4′(1H)-dione has been subjected to the Mannich condensation to give 1-substituted derivatives. With one exception, all of the products were inactive in an anticonvulsant screen. 相似文献
9.
Rodolfo Nesi Stefano Chimichi Francesco De Sio Mirella Scotton 《Magnetic resonance in chemistry : MRC》1983,21(1):42-45
The 13C NMR spectra of a number of pyridazine derivatives have been recorded in DMSO-d6 solution and analysed. Examination of the most diagnostic resonances, with particular emphasis on those arising from the pyridazine ring system, enabled the ready establishment of the presence of a ring-chain tautomerism in 5-(o-aminophenylcarbamoyl)pyridazine-4-carboxylic acid, methyl 5-(o-aminophenylcarbamoyl)pyridazine-4-carboxylate, 5-(o-aminophenylcarbamoyl)-3,6,-dimethylpyridazine-4-carboxylic acid and 5-(2-amino-1,2-dicyanovinylenecarbamoyl)pyridazine-4-carboxylic acid. This gave rise to 3′,4′-dihydro-3′-oxospiro[pyridazine-5(2H),2′(1H)-quinoxaline]-4-carboxylic acid, methyl 3′,4′-dihydro-3′oxospiro[pyridazine-5(2H),2′(1′H)-quinoxaline]-4-carboxylate, 3′,4′-dihydro-3′-oxo-3,6-dimethylspiro[pyridazine-5(2H), 2′(1′H)-quinoxaline]-4-carboxylic acid and 5-oxo-2,3-dicyano-1,4,8,9-tetraazaspiro[5.5]undeca-2,7,10-triene-11-carboxylic acid, respectively. 相似文献
10.
L. Kh. Galstyan K. S. Avetisyan R. A. Tamazyan A. G. Aivazyan 《Russian Journal of Organic Chemistry》2014,50(3):394-397
3a′,8′-Dimethyl-3a′,5′-dihydro-1′H,3′H-dispiro[cyclohexane-1,3′-furo[3,4-f][2]benzofuran-5′,1″-cyclohexane]-1′,7′(4′H)-dione was synthesized by reaction of 3-acetyl-4-methyl-1-oxaspiro[4.5]dec-3-en-2-one with potassium hydroxide in water. 相似文献
11.
Ondrej imo Alfonz Rybr Juraj Alfldi Vladimír Ptoprstý 《Journal of heterocyclic chemistry》1999,36(2):453-456
The 6-(3-hydroxypropylamino)-3-methylpyrimidine-2,4-dione (1) did not afford the expected 6-(3-chloro-propylamino)- derivative on reaction with thionyl chloride, but, instead, the pyrimidine rings were joined via a sulfur bridge to give 9,9′-thiobis(1,2,3,4,7,8-hexahydro-7-melnyl-6H-pyrimido[1,6-a]pyrirnidine-6,8-dione) ( 3 ). An identical 9,9′-thiobis- derivative 3 was obtained when reacting thionyl chloride with 1,2,3,4,7,8-hexahydro-7-methyl-6H-pyrimido[1,6-a]pyrimidine-6,8-dione ( 4 ). We suppose the sulfoxide- derivative 2 to be the intermediate of both routes: it underwent reduction to the final sulfide 3 in excess thionyl chloride. 相似文献
12.
Green Synthesis of Spiro[indoline‐3,4′‐pyrazolo[3,4‐b][1,6]naphthyridine]‐2,5′(1′H)‐diones Catalyzed by TsOH in Ionic Liquids
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Bin‐Bin Feng Rong‐Zhang Jin Mei‐Mei Zhang Xiang‐Shan Wang 《Journal of heterocyclic chemistry》2016,53(5):1578-1583
A three‐component reaction of isatin, 3‐methyl‐1‐phenyl‐1H‐pyrazol‐5‐amine, and piperidine‐2,4‐dione was treated in ionic liquids catalyzed by TsOH and provided an efficient and green method for the synthesis of spiro[indoline‐3,4′‐pyrazolo[3, 4‐b][1,6]naphthyridine]‐2,5′(1′H)‐dione derivatives in high yields. 相似文献
13.
Hexahydro-2(1H)-quinazolinones and-thiones show a reactive behaviour similar to that of dihydro-2(1H)-pyrimidinones (-thiones) and of tetrahydrospiro[cyclohexane-1,4′(1′H)-quinazoline]-2′(3′H)-ones (-thiones), resp. 相似文献
14.
Krishna C. Joshi Renuka Jain Anshu Dandia Saroj Garg Nidhal Ahmed 《Journal of heterocyclic chemistry》1989,26(6):1799-1802
A new spiroheterocyclic system spiro[9H-acridine-9,3′-[3H]indol]-2′(1′H)-one and related compounds have been prepared by the reaction of spiro[3H-indole-3,9′-[9H]xanthen]-2(1H)-ones with aromatic amine or ammonium acetate. The latter were prepared by heating fluorinated indole-2,3-diones with m-/p-cresols or α-naphthol in the presence of sulphuric acid at 230-240°. The synthesized compounds have been characterized on the basis of their elemental analyses, ir, nmr (1H, 13C, 19F) and mass spectral data. 相似文献
15.
Nawal Mishriky Adel S. Girgis Hanaa M. Hosni Hanaa Farag 《Journal of heterocyclic chemistry》2006,43(6):1549-1556
16.
3-[1′(1′H)-Substituent-pyrazol-5′-yl]benzo[5,6]coumarins and 3-(1′,2′-oxazol-5′-yl)benzo[5,6]coumarin were prepared via condensation of 3-(2′-formyl-1′-chlorovinyl)benzo[5,6] coumarin with hydrazine derivatives or hydroxylamine.Reaction of 3-[1′(1′H)-pyrazol-5′-yl]benzo[5,6]coumarin with alkyl halides,olefinic compunds or acid chlorides are described. 相似文献
17.
Ya-Hang Wu Prof. Dr. Hongyan Xiao Prof. Dr. Bin Chen Prof. Dr. Richard G. Weiss Prof. Dr. Yu-Zhe Chen Prof. Dr. Chen-Ho Tung Prof. Dr. Li-Zhu Wu 《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2020,132(25):10259-10264
Three rigid and structurally simple heterocyclic stilbene derivatives, (E)-3H,3′H-[1,1′-biisobenzofuranylidene]-3,3′-dione, (E)-3-(3-oxobenzo[c] thiophen-1(3H)-ylidene)isobenzofuran-1(3H)-one, and (E)-3H,3′H-[1,1′-bibenzo[c] thiophenylidene]-3,3′-dione, are found to fluoresce in their neat solid phases, from upper (S2) and lowest (S1) singlet excited states, even at room temperature in air. Photophysical studies, single-crystal structures, and theoretical calculations indicate that large energy gaps between S2 and S1 states (T2 and T1 states) as well as an abundance of intra and intermolecular hydrogen bonds suppress internal conversions of the upper excited states in the solids and make possible the fluorescence from S2 excited states (phosphorescence from T2 excited states). These results, including unprecedented fluorescence quantum yields (2.3–9.6 %) from the S2 states in the neat solids, establish a unique molecular skeleton for achieving multi-colored emissions from upper excited states by “suppressing” Kasha's rule. 相似文献
18.
Krishna C. Joshi Anshu Dandia Sangeeta Sanan 《Journal of heterocyclic chemistry》1989,26(5):1397-1400
The reaction of 3-(2-oxocycloalkylidene)indol-2-one 1 with thiourea and urea derivatives has been investigated. Reaction of 1 with thiourea and urea in ethanolic potassium hydroxide media leads to the formation of spiro-2-indolinones 2a-f in 40–50% yield and a novel tetracyclic ring system 4,5-cycloalkyl-1,3-diazepino-[4,5-b]indole-2-thione/one 3a-f in 30–35% yield. 3-(2-Oxocyclopentylidene)indol-2-one afforded 5′,6′-cyclopenta-2′-thioxo/ oxospiro[3H-indole-3,4′(3′H)pyrimidin]-2(1H)-ones 2a,b and 3-(2-oxocyclohexylidene)indol-2-one gave 2′,4′a,5′,6′,7′,8′- hexahydro-2′-thioxo/oxospiro[3H-indole-3,4′ (3′H)-quinazolin]-2(1H)-ones 2c-f . Under exactly similar conditions, reaction of 1 with fluorinated phenylthiourea/cyclohexylthiourea/phenylurea gave exclusively spiro products 2g-1 in 60–75% yield. The products have been characterized by elemental analyses, ir pmr. 19F nmr and mass spectral studies. 相似文献
19.
Methyl 3-aroyl-1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates reacted with 3-amino-5,5-dimethylcyclohex-2-en-1-one having no substituent on the nitrogen atom to give 3-aroyl-4-arylamino-6′,6′-dimethyl-6′,7′-dihydro-5H-spiro[furan-2,3′-indole]-2′,4′,5′(1′H,5′H)-triones or methyl 12-aroyl-11-aryl-9-hydroxy-5,5-dimethyl-3,10-dioxo-8,11-diazatricyclo[7.2.1.02,7]dodec-2(7)-ene-1-carboxylates. The latter underwent thermal recyclization to 3′-aroyl-1′-aryl-4′-hydroxy-6,6-dimethyl-6,7-dihydrospiro[indole-3,2′-pyrrole]-2,4,5′(1H,1′H,5H)-triones. 相似文献
20.
KlÁra GÁll-IstÓk Lili Sterk GÁbor TÓth Gyula Deák 《Journal of heterocyclic chemistry》1984,21(4):1045-1048
1-(2′-Chloroacetylamino)-4,4-dimethyl-1,4-dihydro-3(2H)-isoquinolinone ( 3 ) was cyclised by treatment with sodium hydride in dimethyl sulphoxide containing 0.1 % of water to give 10,10-dimethyl-6,7,9,10-tetrahydro-5H,14bH-isoquino[2,1-d][1,4]benzodiazepine-6,9-dione ( 4 ) in a yield of 80%. In anhydrous dimethyl sulphoxide the main product of the reaction was 5-N-(4,4-dimethyl-1-phenyl-1,4-dihydro-3(2H)-isoquinolinon-1′-yl)isoquino[2,1-d][1,4]benzodiazepine-6,9-dione ( 5 ), which was also prepared by the reaction of 3 with 4 . 相似文献