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1.
N-Methylmorpholinium 6-oxo-3,5-dicyano-1,4,5,6-tetrahydro-4-(spirocyclopentane)pyridine-2-thiolate was obtained by reaction
of cyclopentylidenecyanoacetic ester with cyanothioacetamide or cyclopentylidenecyanothioacetamide with cyanoacetic ester
in the presence of N-methylmorpholine; it is used in synthesis of substituted 2-alkylthiotetrahydropyridines, 5-oxo-6,8-dicyano-2,3,6,7-tetrahydro-(5H)-7-(spirocyclopentane)-thiazolo[3,2-a]pyridine, 5-allyl-2-methylthio-3,5-dicyano-4,5-dihydro-4-(spirocyclo-pentane)pyridin-6(1H)-one, and 3-amino-6-oxo-5-cyano-4,5-dihydro-4-(spirocyclopentane)-2H-pyrazolo[5,4-b]pyridin-6(7H)-one.
T. G. Shevchenko Lugansk State Pedagogical Institute, Lugansk 348011, Ukraine, N. D. Zelinskii Institute of Organic Chemistry,
Russian Academy of Sciences, Moscow 117913, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 208–212,
February, 1998. 相似文献
2.
S. G. Krivokolysko V. D. Dyachenko E. B. Rusanov V. P. Litvinov 《Chemistry of Heterocyclic Compounds》2001,37(4):477-483
The reaction of aromatic aldehydes with cyanothioacetamide and ethyl cyanoacetate in the presence of N-methylmorpholine gives N-methylmorpholinium 4-aryl-3,5-dicyano-6-oxo-1,4,5,6-tetrahydro-2-pyridinethiolates, which are used in the synthesis of substituted 2-alkylthiotetrahydropyridines. X-ray diffraction analysis was used to study the structure of 4,5-trans-3,5-dicyano-4-(2-methoxyphenyl)-2-methylthio-6-oxo-1,4,5,6-tetrahydropyridine. 相似文献
3.
Aminomethylation of 3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates upon treatment with primary amines and excess
formaldehyde leads to 3,7-diazabicyclo[3.3.1]nonane derivatives. N-Methylmorpholinium 4-(2-chlorophenyl)-3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolate was obtained by the reaction
of (E)-3-(2-chlorophenyl)-2-cyanoprop-2-enethioamide with 1-cyanoacetyl-3,5-dimethylpyrazole and N-methylmorpholine in acetone in quantitative yield.
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2397–2400, December, 2007. 相似文献
4.
Carlos Peinador Vicente Ojea Jos Ma. Quintela 《Journal of heterocyclic chemistry》1992,29(7):1693-1702
Ready, convenient synthesis for 8-cyano-7-ethoxy-4-oxo-9-phenyl-2-substituted-1,2,3,-4-tetrahydropyrido-[3′,2′:,4,5]thieno[3,2-d]pyrimidines 5 , 8-cyano-7-ethoxy-4-oxo-9-phenyl-2-substituted-3,4-dihydropyrido[3′,2-: 4,5]thieno[3,2-d]pyrimidines 6 , 4-chloro-8-cyano-7-ethoxy-9-phenyl-2-substitutedpyrido[3′,2′:4,5]thieno[3,2-4 -pyrimidines 7 and 8-cyano-7-ethoxy-2-(2′-nitrophenyl)-9-phenyl-4-substitutedpyrido[3′,2′:4,5]thieno[3,2- d ]pyrimidines 8-18 from 2-chloro-3,5-dicyano-6-ethoxy-4-phenylpyridine 1 via 3,5-dicyano-6-ethoxy-2-mercapto-4-phenylpyridine 2 and aminocarboxamide 4 are reported. In addition, the reaction of hydrazino derivative 12 with reagents such as formic acid and triethyl orthoformate yielded the fused tetraheterocyclic 8-cyano-9- ethoxy-5-(2′-nitrophenyl)- 7-phenylpyrido[3′,2′:4,5]thieno[2,3-e]-1, 2,4-triazolo[4,3-c]pyrimidine system 19 . 相似文献
5.
V. D. Dyachenko A. A. Nikishin I. E. Dyachenko 《Russian Journal of Organic Chemistry》2011,47(8):1214-1221
The reaction of ethyl isopropylidenecyanoacetate with ethyl 3-amino-3-thioxopropanoate gave rise to ethyl 4,4-dimethyl-6-oxo-2-thioxo-5-cyanopiperidine-3-carboxylate
whose alkylation provided ethyl 2-benzylsulfanyl-4,4-dimethyl-6-oxo-5-cyano-1,4,5,6-tetrahydropyridine-3-carboxylate, ethyl
5-benzyl-2-benzylsulfanyl-4,4-dimethyl-6-oxo-5-cyano-1,4,5,6-tetrahydropyridine-3-carboxylate, and ethyl 7,7-dimethyl-5-oxo-6-cyano-3,5,6,7-tetrahydro-2H-thiazolo[3,2-a]pyridine-8-carboxylate. 相似文献
6.
V. D. Dyachenko 《Russian Journal of Organic Chemistry》2006,42(5):724-734
Cross-recyclization of 4-aryl(heteryl)-2,6-diamino-3,5-dicyano-4H-thiopyrans with α-bromoketones or alkyl halides formed substituted 3-aryl-2-(4-R-thiazol-2-yl)acrylonitriles, 2-alkylsulfanyl-1,4-dihydropyridines, 2,3,4,7-tetrahydrothiazolo[3,2-a]pyridine, and 4,7-dihydrothieno[2,3-b]pyridine. 相似文献
7.
4-Methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridine ( 3 ) was synthetized from 2-acetylfuro[3,2-f]benzo[b]furan ( 4 ) or from 2-acetyl-5,6-dihydrofuro[3,2-f]benzo[b]furan ( 10 ). The key step involves a rearrangement-cyclization of azides 6 and 12 to form 4-methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridin-1(2H) one ( 7 ) and 8,9-dihydro-4-methylfuro[3′,2′:5,6]benzofuro[3,2c]pyridin-1(2H)-one ( 13 ). Introduction of an aminoalkyl chain on carbon 1 was effected by substitution of 1-chloro-4-methylfuro[3′,2′:5,6]benzofuro[3,2-c]pyridine ( 8 ). 相似文献
8.
The synthesis of 7,8‐dihydro‐5(6H)‐quinolinone ( 3 ) from commercially available 3‐amino‐2‐cyclohexen‐1‐one ( 1 ) and 3‐(dimethylamino)acrolein ( 4 ) in 23% yield avoids the preparation of propynal ( 2 ). Conversion of 5‐(4‐methylphenylsulfonyl)‐6,7,8,9‐tetrahydro‐5H‐pyrido[3,2‐b]azepine ( 12 ) to 6‐(4‐methylphenylsulfonyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐d]pyrido[3,2‐b]azepine ( 24 ) is described. Removal of the N‐(4‐methylphenylsulfonyl) group with 40% sulfuric acid in acetic acid gave the tricyclic azepine 26. Application of a similar series of reactions to 5‐(4‐nitrobenzoyl)‐6,7,8,9‐tetrahydro‐5H‐pyrido[3,2‐b]‐azepine ( 13 ) afforded 6‐(4‐nitrobenzoyl)‐1,4,5,6‐tetrahydropyrazolo[3,4‐d]pyrido[3,2‐b]azepine ( 25 ). 相似文献
9.
S. Yu. Solov'eva-Yavits S. M. Ramsh A. I. Ginak 《Chemistry of Heterocyclic Compounds》1981,17(4):340-343
It is shown that the aminomethylation of 2-iminothiazolidin-4-one and its 5-methyl and 5-arylidene derivatives in an alcohol medium leads to the formation of 6-oxo-2,3,4,5,6,7-hexahydrothiazolo [3,2-a]-1,3,5-triazines. The structures of the compounds obtained were confirmed by their IR, PMR, and UV spectra.See [1] for Communication 39.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 4, pp. 477–480, April, 1981. 相似文献
10.
John W. Mcfarland William A. Essary Lale Cilenti William Cozart Philip E. Mcfarland 《Journal of heterocyclic chemistry》1975,12(4):705-707
Furo[3,2-c] pyridine (I) was nitrated to give 2-nitrofuro[3,2-c]pyridine (II). Bromination and chlorination of I gave, respectively, 2,3-dibromo-2,3-dihydrofuro[3,2-c]pyridine (III) and 2,3-dichloro-2,3-dihydrofuro[3,2-c]pyridine (IV). Oxidation of I with hydrogen peroxide afforded furo[3,2-c]pyridine 5-oxide (V) which was converted to I by phosphorus trichloride and to 4-chlorofuro[3,2-c]pyridine (VI) by phosphorus oxychloride. 相似文献
11.
A. D. Dyachenko S. M. Desenko V. D. Dyachenko A. N. Chernega 《Chemistry of Heterocyclic Compounds》2004,40(5):650-659
Partially hydrogenated thiazolo[3,2-a]pyridines have been synthesized by the interaction of functionally substituted ammonium di- and tetrahydropyridine-2-thiolates with bromocyclohexanone. The structure of 6,8-dicyano-3-hydroxy-5-oxo-1,3-tetramethylene-2,3,4,5,6,7-hexahydrospiro[thiazolo[3,2-a]pyridine-7,1'-(4'-methylcyclohexane)] has been determined by X-ray crystallography. 相似文献
12.
L. H. Klemm Susan Johnstone Sandip K. Sur Daniel R. Muchiri 《Journal of heterocyclic chemistry》1989,26(5):1277-1281
Three compounds, thieno[3,2-b]pyridine 4-oxide, 7-nitrothieno[3,2-b]pyridine 4-oxide ( 1 c), and 6-cyano-thieno[2,3-b]pyridine, undergo nitration by means of a mixture of nitric and sulfuric acids to yield 3,7-dinitro-thieno[3,2-b]pyridine (3%), 3,7-dinitrothieno[3,2-b]pyridine 4-oxide ( 1d ) (26%), and 6-carbamoyl-5-nitrothieno[2,3-b]pyridine ( 6b ) (11%), respectively. Structures of the products were ascertained by spectral means, notably infrared, 1H nmr, and 13C nmr. It is proposed that 1d exists (at least in part) as a tricyclic structure and that 6b may result from an intramolecular mechanism of nitration. An attempt to de-N-oxygenate 1c with excess triphenylphosphine removes more than one oxygen atom per molecule (as triphenylphosphine oxide) without producing an identified thienopyridine product. 相似文献
13.
A convenient synthesis of furo[3,2-b]pyridine and its 2- and 3-methyl derivatives from ethyl 3-hydroxypiconate ( 1 ) is described. The hydroxy ester 1 was O-alkylated with ethyl bromoacetate or ethyl 2-bromopropionate to give the diester 2a or 2b . Cyclization of compound 2a afforded ethyl 3-hydroxyfuro[3,2-b]pyridine-2-carboxylate ( 3 ) which in turn was hydrolyzed and decarboxylated to give furo[3,2-b]pyridin-3-(2H)-one ( 4a ). Cyclization of 2b gave the 2-methyl derivative 4b . Reduction of 4a and 4b with sodium borohydride yielded the corresponding hydroxy derivative 5a and 5b respectively, which were dehydrated with phosphoric acid to give furo[3,2-b]pyridine ( 6a ) and its 2-methyl derivative ( 6b ). 2-Acetylpyridin-3-ol ( 8 ) was converted to the ethoxycarbonylmethyl ether ( 9 ) by O-alkylation with ethyl bromoacetate, which was cyclized to give 3-methylfuro[3,2-b]pyridine-2-carboxylic acid ( 10 ). Decarboxylation of 10 afforded 3-methylfuro[3,2-b]pyridine ( 11 ). 相似文献
14.
L. M. Potikha A. R. Turelyk V. A. Kovtunenko A. V. Turov 《Chemistry of Heterocyclic Compounds》2010,46(2):223-231
A method for the synthesis of derivatives of [1, 3]thiazolo[3,2-a]pyridines, pyrido[2,1-b][1, 3]benzo-thiazole, [1, 3, 4]thiadiazolo[3,2-a]pyridine, and [1, 2, 4]triazolo[4,3-a]pyridine, which includes base initiated cyclization of quaternary azolium salts, formed by the interaction of (Z)-1,3-diaryl-4-bromo-2-buten-1-ones with 1-alkyl-1H-1,2,4-triazoles, 4-methyl-1,3-thiazole, 1,3-benzothiazole, and N-phenyl-1,3,4-thiadiazole-2-amine.
Derivatives of 2-chloroimidazo[1,2-a]pyridine were obtained when 5-chloro-1-methyl-1H-imidazole was used. 相似文献
15.
A four-step synthesis of 5-carboxamidopyrrolo[3,2-b]pyridine ( 3 ) from pyrrolo[3,2-b]pyridine ( 4 ) is described (45% overall yield). The one-step conversion of the N-oxide 6 of the pyrrolo[3,2-b]pyridine 5 leads to the 5-cyanopyrrolo[3,2-b]pyridine 7. The cyano group is hydrolyzed to afford the title compound 3 , which is the 4-aza analog of the indole backbone in 5-carboxamidotryptamine, a potent agonist of the neurotransmitter, serotonin. 相似文献
16.
Emile Bisagni Alain Civier Jean-Pierre Marquet 《Journal of heterocyclic chemistry》1975,12(3):461-465
Treatment of 4-hydroxy-6-methylpyran-2-one with chloracetalhyde in basic aqueous medium gave 6-methylfuro[3,2-c]pyran-4-one. This compound reacted with ammonium hydroxide and some primary amines to form the corresponding N-substituted furo[3,2-c]pyrid-4-ones which may also be obtained from 4-hydroxy-α-pyridones. Furo[3,2-c]pyran-4-one was acylated at the 2 position and 4-chloro-6-methylfuro[3,2-c]pyridine easily gave 4-substituted derivatives by displacement of the halogen atom. 相似文献
17.
V. N. Nesterov V. D. Dyachenko Yu. A. Sharanin Yu. T. Struchkov 《Russian Chemical Bulletin》1994,43(1):118-120
The synthesis of 2-allylseleno-3,5-dicyano-6-hydroxy-4-phenylpyridine has been carried out and its cyclization into 6,8-dicyano-5-hydroxy-3-iodomethyl-7-phenyl-2,3-dihydroselenazolo[3,2-a]pyridinium triiodide has been studied. X-ray investigation shows that allylselenopyridine in the crystalline state exists as hydroxy derivative and the allyl substituent is approximately perpendicular to the heterocyclic plane. In crystal the molecules are linked by hydrogen bonds forming dimers.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 122–124, January, 1994. 相似文献
18.
Ronald G. Sutherland Adam Pirko Choi Chuck Lee Stanley H. Simonsen Vincent M. Lynch 《Journal of heterocyclic chemistry》1988,25(6):1911-1916
Synthesis of the heterocyclic skeletons of some biologically active compounds from (η6-o-dichlorobenzene)(η5-cyclopentadienyrl)iron hexafluorophosphate in a two step procedure is described. Cyclopentadienyliron hexafluorophosphate complexes of 1,4-benzodioxino[2,3-b]pyridine, 1,4-benzoxathiino[3,2-b]pyridine, 10H-pyrido[3,2-b]benzoxazine, benzo[b]naphtho[2,3-e][1,4]dioxin, 4-methylbenzo[b]benzopyran-2-one[7,6-e][1,4]dioxin and benzo[b]anthracen-9,10-diono[1,2-e][1,4]dioxin were isolated and characterized. Upon pyrolytic sublimation of these complexes the free heterocycles were obtained and characterized. (η6-1,4-Benzoxathiino[3,2-b]pyridine)(η5-cyclopentadienyl)iron hexafluorophosphate crystalizes in the orthothombic system, space group Pbca; the dihedral angle between the planes of outer rings was found to be 176.8 (1). 相似文献
19.
Dyachenko V. D. Dyachenko A. D. Chernega A. N. 《Russian Journal of Organic Chemistry》2004,40(3):397-406
Cyclopentylidene- and cyclohexylidene(cyano)acetamides reacted with malononitrile and cyano-(thioacetamide) according to the Michael pattern with exchange of the methylene components to give substituted 1-amino-2,6,6-tricyano-1,3-cyclohexadienes and thieno[2,3-d]pyrimidine-4(3H)-thiones. Condensation of cyclopentylidene- and cyclohexylidene(cyano)acetamide with 1,3-dicarbonyl compounds afforded 4,6-di-methyl-3-cyanopyridine-2(1H)-thione and morpholinium 4-methyl-6-oxo-3-cyano-1,6-dihydropyridine-2-thiolate which were converted into substituted 2-alkylsulfanylpyridines, thieno[2,3-b]pyridines, thiazolo[3,2-a]pyridine, and 2H-[1,3]thiazino[3,2-a]pyridine. 相似文献
20.
Treatment of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with an excess of isobutyraldehyde and primary aromatic amines in refluxing ethanol gives the corresponding 7-aryl-3-arylamino-2,2-dimethyl-5-oxo-2,3,6,7-tetrahydro-5 H-thiazolo[3,2-a]pyridine-8-carbonitriles in 18-38 % yields. 相似文献