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1.
Pyrido[3,2:4,5]thieno[2,3-c]cinnolines, new heterocyclic compounds, were obtained in three steps: 1) alkylation of 3-cyanopyridine-2(1H)-thiones by o-nitrobenzyl bromide to give 2-(o-nitrobenzyl)thio-3-cyanopyridines, 2) closure of the thiophene ring in these intermediates to give 3-amino-2-(o-nitrophenyl)thieno[2,3-b]pyridines, and 3) closure of the pyridazine ring by condensation of the amino and nitro groups in triethyl phosphite, leading to the final heterocyclic system.N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 104–109, January, 1998.  相似文献   

2.
<正>Reactions of the 6-hydroxy-thiopyrano[3,4-c]pyridine-5-carbonitrile derivative 1 withα-halo-carbonyl compounds gave the ortho-substituted intermediates 2a-c which were converted into furo[2,3-b]thiopyrano[4,3-d]pyridines 3a-c by fusion of a furan moiety under basic conditions.Further cyclization of 3a-c led to a fusion of a pyrimidine ring,yielding the tetracyclic products 6,7 and 8.In addition,condensation of 6 with various aromatic aldehydes afforded the corresponding imines 9a,b.Mannich reaction of 7 gave products 10a,b.  相似文献   

3.
Summary 8,9-Diphenylpyridazino[4,3:4,5]thieno[3,2-d]-1,2,3-triazin-4(3H)-one (2), 3-substituted 8,9-diphenylpyridazino[4,3:4,5]thieno[3,2-d]-1,2,3-triazin-4(3H)-ones (3a–c), 3,4-diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazin-8(7H)-one (4), 8-chloro-3,4-diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazine (5), 8-substituted 3,4-diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazines (6a–h) and 7-substituted 3,4-diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazin-8(7H)-ones(7a–c) were synthesized from 5-amino-3,4-diphenylthieno[2,3-c]pyridazine-6-carboxamide (1).
Synthese neuer Pyridazino[4,3:4,5]thieno[3,2-d]-1,2,3-triazin-und Pyrimido[4,5:4,5]thieno[2,3-c]pyridazin-Derivate
Zusammenfassung Folgende Verbindungen wurden ausgehend von 5-Amino-3,4-diphenylthieno[2,3-c]pyridazin-6-carboxamid (1) synthetisiert: 8,9-Diphenylpyridazino[4,3:4,5]thieno[3,2-d]-1,2,3-triazin-4(3H)-on (2), 3-substituierte 8,9-Diphenylpyridazino[4,3:4,5]thieno[3,2-d]-1,2,3-triazin-4(3H)-one (3a–c), 3,4-Diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazin-8[7H]-on (4), 8-Chlor-3,4-diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazin (5), 8-substituierte 3,4-Diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazine (6a–h) und 7-substituierte 3,4-Diphenylpyrimido[4,5:4,5]thieno[2,3-c]pyridazin-8(7H)-one (7a–c).
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4.
3-Phenyl-5-methyl(phenyl)-1H,3H-pyrimido[4,5:4,5]pyrimido[1,2-a]benzimi-dazole-2,4-diones were obtained by the cyclization of N-phenyl-N-[3-ethoxycar-bonyl-4-methyl(phenyl)pyrimido [1,2-a]benzimidazol-2-yl]ureas by the action of potassium carbonate. 2-Methyl-5-phenyl-1H-pyrimido[4,5:4,5]pyrimido[1,2-a]benzimidazol-4-one was obtained by the reaction of N-3-ethoxycarbonyl-4-phenylpyrimido[1,2-a]benzimidazol-2-yl]-N,N-dimethylacetamidine with ammonium acetate in ethanol. The synthesized compounds are members of a new heterocyclic system. The molecular and crystal structure of the solvate of 3-phenyl-5-methyl-1H,3H-pyrimido[4,5:4,5] pyrimido[1,2-a]benzimidazole-2,4-dione with two molecules of DMF was studied by x-ray crystallographic analysis.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2587–2592, November, 1991.  相似文献   

5.
4-Oxo-6, 11-dihydro-4H-thieno[3, 2.-5,6]-pyrinudo[1, 2-b]isoquinolines have been synthesized by the reaction of o-bromo-methylphenylacetonitrile with esters of substituted 2-aminothiophene-3-carboxylic acids. They were characterized as the hydrobromides and as the fee bases. The tautonterism of the bases in DMSO solution is discussed.For Communication 6. see[1].T. G. Shevchenko Kiev University, Kiev, 252017. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 366–369, March, 1996. Original article submitted September 9, 1995.  相似文献   

6.
Alkylatio of 2-piperidinomethylene-2H-pyrrolo[1,2-a]indole-3,9-dione with dimethyl sulfate, followed by hydrolysis of the intermediate immonium salts. yielded 2-formyl derivatives, the reaction of which with substances possessing on active methylene unit leads to the formation of 2-substituted vinyl-3-oxo-9-alkoxypyrrolo[1,2-aindoles. Cyclization of the 9-methoxy derivative yielded a new heterocyclic system of 2-amino-3-cyano-5H-4,5-dihydropyrodol[32:4,5]pyrroloindoledione-4,11.Center for the Chemistry of Drugs, S. Ordzhonikidze All-Russian Scientific Research Institute Moscow119021 Translated from Khimiya Geterotsiklicheskikh Soedinenii.No. 8, pp, 919–925, August, 1994. Orginally article submitted June 22, 1994.  相似文献   

7.
Research on Chemical Intermediates - The synthesis of (6-ethyl-1,6-dihydropyrrolo[3,2-c]carbazol-2-yl)methanol 5 and...  相似文献   

8.
Russian Chemical Bulletin - New pyrido[2′,3′:3,4]pyrazolo[5,1-c][1,2,4]triazin-4(6H)-one derivatives were synthesized from accessible 1,2,4-triazine and pyrazolo[5,1-c][1,2,4]triazine...  相似文献   

9.
1,4-Dihydro-3-cyano-2-pyridinethiolates react with 2-bromo-l-(4-bromophenyl)ethylidenemalononitrile or N-cyanochloracetanudine to give 6, 9-dihydropyrido[3, 2': 4, 5]thieno[3. 2-b]pyridines or 6, 9-dihydropyrido-[3.2:4.5Jthieno(3,2-d]pyrimidines, respectively.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 553–556, April, 1996.  相似文献   

10.
Alkylation of 11-benzyl-3,11-dihydro-4H-pyrimido[5′,4′:5,6]pyrido[3,2-b]indol-4-one with methyl iodide and methyl bromoacetate in DMF gave 3-alkylpyrimidopyridoindolones as the corresponding salts. The reaction in acetone in the presence of K2CO3 yielded 3,6-disubstitution products. Alkylation with DMF dimethyl acetal gave a mixture of the 3- and 6-alkylpyrimidopyridoindol-4-one bases. The structure of 4-oxo-4,6-dihydro-3H-pyrimido-[5′,4′:5,6]pyrido[3,2-b]indol-11-ium chloride (3b) was proved by X-ray diffraction analysis.  相似文献   

11.

A method for the synthesis of previously unknown pyrido[3´,2´:4,5]thieno[3,2-c]isoquinolin-5(6H)-ones was suggested, which includes a condensation reaction of substituted 3-cyanopyridine-2(1H)-thiones with methyl 2-(chloromethyl)benzoate and subsequent treatment of the condensation products with potassium tert-butoxide. The oxidation of the condensation products to sulfoxides or sulfones and subsequent treatment of these compounds with potassium tert-butoxide led to substituted pyrido[3´,2´:4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11-oxides or substituted pyrido[3´,2´:4,5]thieno[3,2-c]isoquinolin-5(6H)-one 11,11-dioxides.

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12.
Some new pyrido[3′,2′:4,5]thieno[2,3-e]-[1,2,4]triazolo[4,3-a] pyrimidin-5(4H)-ones were prepared through heterocyclization of ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate with phenyl or ethyl isothiocyanate followed by nucleophilic displacement with hydrazine, and finally cyclocondensation with orthoesters. Correspondence: Abolghasem Davoodnia, Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch, Mashhad 91735-413, Iran.  相似文献   

13.
In the present study, a novel 8,9,10,11-tetrahydro-7H,14H-benzo[4′,5′] thieno[2′,3′:4,5]-1,3-oxazino[3,2-b]isoquinoline-7,14-dione 5 was prepared by condensation of 2-amino-3-carbethoxy-4,5,6,7-tetrahydrobenzothiophene with homophthalic anhydride under microwave irradiation, followed by alkaline hydrolysis and cyclization using acetyl chloride. Compound 5 was further allowed to react with different nitrogen nucleophiles to get new tetrahydrobenzothienopyrimido isoquinolinone derivatives. The structures of the prepared compounds were elucidated by IR, 1H-NMR, 13C-NMR, and mass spectroscopy. The newly prepared compounds were tested in vitro against a panel of two human tumor cell lines, namely, hepatocellular carcinoma (liver) HepG2, and mammary gland breast MCF-7. Almost all the tested compounds showed satisfactory activity.  相似文献   

14.
4-(3-(4-Hydroxyphenyl)-1-phenyl-1H-pyrazol-4-yl)-6-phenyl-2-thioxo-1,2-di hydro-pyridine-3-carbonitrile (1) reacted with ethyl chloroacetate (2) in ethanolic sodium acetate solution to yield the corresponding ethyl (3-cyanopyridin-2-ylsulphanyl)acetate derivative 3. Intramolecular cyclization of compound 3 was achieved by its heating in DMF containing potassium carbonate to afford the corresponding ethyl 3-aminothieno[2,3-b]pyridine-2-carboxylate derivative 4 which reacted with hydrazine hydrate in refluxing pyridine to yield the starting material 3-aminothieno[2,3-b]pyridine-2-carbohydrazide derivative 7. Compound 7 reacted with different reagents such as triethylorthoformate, formic acid, acetic acid and acetic anhydride to afford the target molecules pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidin-4(3H)-one derivatives 8–10, 12 and 13 in good to excellent yields. On the other hand, pyridine-2(1H)-thione derivative 1 reacted with hydrazine hydrate in refluxing pyridine to give the other starting material 3-amino-1H-pyrazolo[3,4-b]pyridine derivative 20 which reacted with acetylacetone under reflux to afford the target molecule pyrido[2′,3′:3,4]pyrazolo[1,5-a]-pyrimidine derivative 21 in a good yield. The structures of target molecules were elucidated using elemental analyses and spectral data.  相似文献   

15.
Russian Journal of Organic Chemistry - 2-Acyl-4,5,6-trialkyl-3-aminothieno[2,3-b]pyridines,...  相似文献   

16.

Pyrdine-2(1H)-thione 1 reacted with ethyl chloroacetate 2 to give 2-S-ethoxy-carbonylmethylpyridine derivative 3, which could be cyclized into thieno[2,3-b]-pyridine-2-carbohydrazide derivative 5 by boiling with hydrazine hydrate. The latter compound reacted with cinnamonitrile derivatives 6a, b, triethylorthoformate, formic acid, dimethylformamide-dimethylacetal, and diethyl carbonate to give the corresponding shiff base 7a, b and pyrido[3′,2′;-4,5]thieno[3,2-d]pyrimidine derivatives 10–13 in respective manner. On the other hand, compound 5 also reacted with carbondisulphide and phenyl isothiocyanate to afford the corresponding 2-(1,3,4-oxadiazolo-2-yl)thieno[2,3-b]pyridine derivatives 18 and 22. Finally, compound 5 reacted with some β-dicarbonyl compounds, such as ethyl acetoacetate, acetylacetone and ethyl β-arylazoacetoacetate, to yield the corresponding 2-(pyrazol-1-yl-carbonyl)thieno[2,3-b]pyridine derivatives 24, 25, and 27 respectively.  相似文献   

17.
Possible approaches to the synthesis of functionalized, pyrimido[5′,4′:4,5]thieno [3,2-c]pyridazines 2-18 , pyridazino[3′,4′:4,5]thieno[2,3-d]triazines 19, 20a,b and pyrido[3′,2′:4,5]thieno[3,2-c]pyridazines 22a,b are described. The sequence involves the heterocyclization of 6-amino-1,3-diphenyl-1,4-dihydrothieno[3,2-c]pyridazine-7-carboxamide (1) with appropriate reagents. The antimicrobial activity of some the newly synthesized compounds was examined. All tested compounds proved to be active as antibacterial and antifungal agents.  相似文献   

18.
19.
The synthesis of N‐substituted pyridothienopyrimidines bearing ethoxymethyl, benzyloxymethyl, methylthiomethyl, benzoylmethyl, allyl, sec‐butyl, and 2‐acetyloxyethyl chains as a sugar mimic was described. The O‐substituted pyridothienopyrimidines were obtained during some reactions.  相似文献   

20.
3-Cyano-2(1H)-pyridinethiones react with N-acetylchloroacetamide in ethanol in the presence of KOH to give pyrido[3,24,5]thieno[3,2-d]pyrimidin-4(3H)-ones.N. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 117913 Moscow. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 837–840, June, 1997.  相似文献   

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