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1.
1,3-Dialkyl-5-amino-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones reacted with acetylacetone to give the corresponding 4-(1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-5-ylamino)pent-3-en-2-ones which underwent intramolecular cyclization to 1,3-dialkyl-5,7-dimethyl-1,3-dihydro-2H-imidazo[4,5-b]-[1,8]naphthyridin-2-ones on heating in polyphosphoric acid or diphenyl ether. Analogous reaction of 1,3-dialkyl-5-amino-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones with ethyl acetoacetate led to the formation of ethyl 3-(1,3-dialkyl-2-oxo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-5-ylamino)but-2-enoates whose cyclization afforded 1,3-dialkyl-8-hydroxy-7-methyl-1,3-dihydro-2H-imidazo[5,4-b][1,8]naphthyridin-2-ones. 相似文献
2.
D. A. Lomov 《Russian Journal of Organic Chemistry》2016,52(1):51-53
Treatment of 5-amino-1,3-dialkyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones with sodium nitrite in aqueous HCl gave 1,3-dialkyl-1H-imidazo[4,5-b]pyridine-2,5(3H,4H)-diones which were nitrated with potassium nitrate in sulfuric acid to 6-nitro derivatives, and the latter underwent recyclization into 4-amino-1,3-dialkyl-5-(1H-pyrazol-5-yl)-2,3-dihydro-1H-imidazol-2-ones by the action of hydrazine hydrate. 相似文献
3.
N. N. Smolyar Kh. Ya. Lopatinskaya A. B. Vasilechko D. A. Lomov Yu. M. Yutilov 《Russian Journal of Organic Chemistry》2007,43(3):417-421
Nitration of 1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one and its N-methyl derivatives at 0–5°C and 60°C gives 5-nitro-and 5,6-dinitro-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones, respectively. The latter can also be obtained by nitration of 5-mononitro derivatives under similar conditions. The nitration of 6-chloro-and 6-bromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones and their N-methyl-substituted analogs leads to the formation of the corresponding 6-chloro(bromo)-5-nitro compounds. The same products are formed in the nitration of 5,6-dichloro-and 5,6-dibromo-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-ones. In this case, the process involves replacement of the halogen atom in position 5 of the pyridine fragment by nitro group. The nitration of 6-bromo-5-methyl-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one is accompanied by oxidation of the 5-methyl group to carboxy. 相似文献
4.
G. P. Kutrov N. V. Kovalenko Yu. M. Volovenko 《Russian Journal of Organic Chemistry》2008,44(2):257-262
2-Cyanomethyl derivatives were obtained of imidazo[1,2-a]pyridine, imidazo[1,2-a]pyrimidine, and imidazo[2,1-b]thiazole, and their reactivity was investigated by an example of imidazo[1,2-a]pyridine: It was subjected to nitration, bromination, azo coupling and nitrosation. Acylation of the methylene group effected by amino acids esters with a subsequent addition of the amino group to the cyano group resulted in the formation of 5-amino-4-imidazo[1,2-a]-pyridin-2-yl-1-phenyl-1,2-dihydro-3H-pyrrol-3-one and 2-amino-1-ethyl-3-imidazol[1,2-a]pyridin-2-yl-4(1H)-quinolinone. 相似文献
5.
A. I. Vas’kevich R. I. Vas’kevich V. I. Staninets S. A. But A. N. Chernega 《Russian Journal of Organic Chemistry》2007,43(10):1526-1531
2-(2-propynylsulfanyl)-5,6,7,8-tetrahydrobenzo[b]thieno[2,3-d]pyrimidin-4(3H)-one with arylsulfenyl chlorides in chloroform gave products of anti-Markownikoff Ad E-addition. The use of nitromethane as solvent in the presence of lithium perchlorate additives favored intramolecular electrophilic cyclization into 1-arylsulfanyl-1,2,6,7,8,9-hexahydro-4H-benzo[4,5]thieno[3,2-e][1,3]thiazolo[3,2-a]-pyrimidin-5-one. 相似文献
6.
Yu. M. Yutilov Kh. Ya. Lopatinskaya N. N. Smolyar S. V. Gres’ko 《Russian Journal of Organic Chemistry》2005,41(4):575-579
Chlorination and bromination of 2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one and its N-methyl-substituted derivatives in acetic acid at 90–95°C leads to formation of the corresponding 5,6-dichloro(dibromo)-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones. Iodination of the same substrates with ICl under analogous conditions yields 6-iodo derivatives. Chlorination of 6-iodo-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one is accompanied by replacement of the iodine atom by chlorine with formation of 5,6-dichloro-1,3-dimethyl-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-one. Bromination of 6-bromo- and 6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones gives 5,6-dibromo- and 5-bromo-6-chloro-2,3-dihydro-1H-imidazo[4,5-b]pyridin-2-ones, respectively.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 4, 2005, pp. 586–589.Original Russian Text Copyright © 2005 by Yutilov, Lopatinskaya, Smolyar, Gres’ko. 相似文献
7.
Reactions of 3-[(2-bromoprop-2-en-1-yl)sulfanyl]-5H-[1,2,4]triazino[5,6-b]indole with bromine and of 3-[(2-methylprop-2-en-1-yl)sulfanyl]-5H-[1,2,4]triazino[5,6-b]indole with iodine and bromine afforded 3-halomethyl-10H-[1,3]thiazolo[3′,2′: 2,3][1,2,4]triazino[5,6-b]indol-4-ium halides whose structures were determined by 1H NMR and X-ray analysis. 相似文献
8.
A. V. Bentya R. I. Vas’kevich A. V. Bol’but M. V. Vovk V. I. Staninets A. V. Turov E. B. Rusanov 《Russian Journal of Organic Chemistry》2008,44(9):1362-1368
6-Allylsulfanyl-1-arylpyrazolo[3,4-d]pyrimidin-4(5H)-ones react with iodine and sulfuric acid to give angular pyrazolothiazolopyrimidine derivatives. The reaction of 6-(prop-2-yn-1-ylsulfanyl)-1-(4-tolyl)-pyrazolo[3,4-d]pyrimidin-4(5H)-one with sulfuric acid gives angularly fused pyrazolo[4,3-e][1,3]thiazolo-[3,2-a]pyrimidin-4-one, whereas in the reaction with sodium methoxide linearly fused pyrazolo[3,4-d][1,3]-thiazolo[3,2-a]pyrimidin-4-one was formed. Linearly fused pyrazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazole derivatives were also obtained by reaction of 1-aryl-6-(3-phenylprop-2-en-1-ylsulfanyl)pyrazolo[3,4-d]pyrimidin-4(5H)-ones with sulfuric acid. 相似文献
9.
Alkylation of pyridin-2(1H)-one and 5-nitropyridin-2(1H)-one with 4-bromobut-1-ene afforded a mixture of N- and O-butenyl derivatives. 1-(But-3-en-1yl)pyridin-2(1H)-one and 1-(but-3-en-1-yl)-5-nitropyridin- 2(1H)-one reacted with bromine and iodine to give 2-(halomethyl)-3,4-dihydro-2H-pyrido[2,1-b][1,3]-oxazinium halides. 相似文献
10.
A new efficient method has been developed for the synthesis of highly biologically active pyrano-[4,3-d]pyrazolo[3,4-b]pyridines on the basis of Smiles rearrangement of ethyl [(8-alkyl(aryl)-5-cyano-3,3-dimethyl-3,4-dihydro-1H-pyrano[3,4-c]pyridin-6-yl)oxy]acetates. Intermediate acetohydrazides have also been isolated. The proposed procedure is advantageous due to the possibility of avoiding experimentally difficult chlorination stage. 相似文献
11.
N. G. Kozlov Yu. D. Zhikharko L. I. Basalaeva 《Russian Journal of Organic Chemistry》2018,54(10):1493-1497
A series of new 11-(R-phenyl)-8,9-dihydro-7H-benzo[f]cyclopenta[b]quinolin-10(11H)-ones and 7,14-bis(R-phenyl)-2,3,9,10,11,14-hexahydrocyclopenta[2,3]quinolino[8,7-h]cyclopenta[b]quinoline-1,8(4H,7H)-diones were synthesized by three-component condensation of naphthalen-2-amine or naphthalene- 1,5-diamine with substituted benzaldehydes and cyclopentane-1,3-dione in one step through intermediate formation of unstable arylaminoketoenol. 相似文献
12.
S. O. Kasatkina E. E. Stepanova M. V. Dmitriev A. N. Maslivets 《Russian Journal of Organic Chemistry》2018,54(7):1055-1060
3-Aroylpyrrolo[1,2-a]quinoxaline-1,2,4(5H)-triones reacted with 2,3-dihydrofuran and 3,4-dihydro-2H-pyran to give mixtures of the corresponding hetero-Diels–Alder (furo- and pyrano[3″,2″: 5′,6′]pyrano- [4′,3′: 2,3]pyrrolo[1,2-a]quinoxalines) and Michael adducts (furyl- and pyranylpyrrolo[1,2-a]quinoxalines). 相似文献
13.
Methylation of 5(6)-nitro-1H-benzimidazole with methyl iodide in the presence of potassium hydroxide and N-methylpyrrolidin-2-one gave a mixture of isomeric 1-methyl-5-nitro- and 1-methyl-6-nitro-1H-benzimidazoles which were reduced with tin in concentrated aqueous HCl on heating. The resulting amines reacted with furan-2-carbonyl chloride in N-methylpyrrolidin-2-one to give furan-2-carboxamides which were treated with excess P2S5 in pyridine. Oxidation of isomeric furan-2-carbothioamides with K3[Fe(CN)6] in alkaline medium afforded a mixture of intramolecular cyclization products, 2-(furan-2-yl)-6-methyl-6H-imidazo[4,5-g][1,3]benzothiazole and 2-(furan-2-yl)-8-methyl-8H-imidazo[4,5-g][1,3]benzothiazole which were separated by column chromatography and identified. 相似文献
14.
N-Allyl-5-amino-1H-pyrazole-4-carboxamides in reactions with polyphosphoric acid, with N-halosuccinimides in chloroform, and with (chlorosulfanyl)benzenes in nitromethane in the presence of lithium perchlorate underwent cyclization involving the N-allylamide fragment to give 4-[5-methyl(halomethyl)-4,5-dihydrooxazol-2-yl]-1H-pyrazol-5-amines and 2-(5-amino-1H-pyrazol-4-yl)-5-[(arylsulfanyl)methyl]-4,5-dihydro-1,3-oxazolium perchlorates, respectively. Analogous reactions of N-propargyl-5-amino-1H-pyrazole-4-carboxamides with polyphosphoric acid afforded 4-(5-methyloxazol-2-yl)-1H-pyrazol-5-amines, and with (chlorosulfanyl) benzenes, 2-(5-amino-1H-pyrazol-4-yl)-5-[(arylsulfanyl)methylidene]-4,5-dihydro-1,3-oxazolium perchlorates. 相似文献
15.
M. V. Dmitriev P. S. Silaichev K. V. Lesnikova M. A. Zheleznova M. A. Ezhikova M. I. Kodess A. N. Maslivets 《Russian Journal of Organic Chemistry》2018,54(9):1358-1362
Dimethyl 1-aryl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2,3-dicarboxylates reacted with 3-arylamino-1H-inden-1-ones to give the corresponding methyl 1-aryl-3-[2-(arylamino)-2-oxoacetyl]-2,5-dioxo-2,5-dihydro-1H-indeno[1,2-b]pyridine-4-carboxylates. 相似文献
16.
V. N. Britsun 《Russian Journal of Organic Chemistry》2008,44(10):1528-1531
Reactions of N-aryl-3-oxobutanethioamides with 1H-1,2,4-triazole-5-amine give mixtures of 7-arylamino-5-methyl[1,2,4]triazolo[1,5-a]pyrimidines, 5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-7-thione, 7-methyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-5-thione, and 5-arylamino-7-methyl[1,2,4]triazolo[ 1,5-a]pyrimidines whose ratio depends on the substituent in the aryl group of initial N-aryl-3-oxobutanethioamide and solvent nature (the presence of a proton-donor solvent). 相似文献
17.
L. M. Gornostaev Yu. G. Khalyavina A. S. Kuznetsova O. I. Fominykh D. A. Tropina E. V. Murashova I. A. Zamilatskov V. V. Chernyshev 《Russian Journal of Organic Chemistry》2016,52(1):80-86
Reactions of 2-alkylamino-1,4-naphthoquinones with 2,2-dihydroxy-1H-indene-1,3(2H)-dione afforded 13-alkylbenzo[f]isochromeno[4,3-b]indole-5,7,12(13H)-triones. 相似文献
18.
V. E. Zhulanov M. V. Dmitriev A. N. Maslivets 《Russian Journal of Organic Chemistry》2017,53(10):1531-1536
Thermolysis of methyl 3-acyl-1-[(diphenylmethylidene)amino]-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates generates 4-acyl-1-(diphenylmethylidene)-3-(methoxycarbonyl)-1H-pyrazol-1-ium-5-olates which react with alkenes to give methyl 3-acyl-7,7-diphenyl-6,7-dihydro-5H-pyrazolo[5,1-b][1,3]oxazine-2- carboxylates. The product structure was confirmed by X-ray analysis. 相似文献
19.
S. V. Fedoseev M. Yu. Belikov O. V. Ershov V. A. Tafeenko 《Russian Journal of Organic Chemistry》2017,53(11):1660-1663
A method was developed for the synthesis of 4-halo-3-(phenylamino)-furo[3,4-c]pyridin-1(3H)-ones by the reaction of 4-halo-3-hydroxyfuro[3,4-c]pyridin-1(3H)-ones with aniline at room temperature. 相似文献
20.
A. G. Mikhailovskii A. S. Yusov O. V. Gashkova 《Russian Journal of Organic Chemistry》2016,52(2):223-227
Acylation of 1-methyl-3,3-dialkyl-3,4-dihydroisoquinolines with acid chlorides afforded enaminoketones. Enaminophenylketones from the obtained series were reacted with oxalyl chloride to provide 1-benzoyl-5,5-dialkyl-2,3,5,6- tetrahydropyrrolo[2,1-a]isoquinoline- 2,3-diones. The reaction of the latter with binucleophiles leads to the opening of the pyrrole ring and to the heterocyclization: Under the effect of o-phenyldiamine qinoxaline is formed, 1,2-cyclohexanediamine provides the hexahydro-benzimidazole system, о-aminophenol gives benzoxazole, 3-hydroxy-2-amino-pyridine furnishes oxazolo[4,5-b]pyridine. In the reaction with hydrazine hydrate the acylation occurs with hydrazide formation. 相似文献