共查询到20条相似文献,搜索用时 31 毫秒
1.
E. N. Ulomskiy N. R. Medvedeva A. V. Shchepochkin O. S. Eltsov V. L. Rusinov O. N. Chupakhin E. G. Deeva O. I. Kiselev 《Chemistry of Heterocyclic Compounds》2011,47(9):1164-1169
The reaction of 3-R-5-amino-1,2,4-triazoles with the ethyl ester of 2-fluoroacetoacetic acid gave 2-R-fluoro[1,2,4]triazolo[1,5-a]pyrimidin-7(4H)-ones. The reaction of a 3-R-1,2,4-triazolyl-5-diazonium salt with the ethyl ester of 2-fluoroacetoacetic acid and subsequent
cyclization of the triazolylhydrazones lead to 7-R-3-fluoro[1,2,4]triazolo[5,1-c][1,2,4]triazin-4(1H)-ones. 相似文献
2.
V. A. Mamedov L. V. Mustakimova A. T. Gubaidullin I. A. Litvinov Ya. A. Levin 《Russian Journal of Organic Chemistry》2004,40(9):1309-1317
4-Amino-3-(2-R-5-phenylthiazol-4-yl)-1,2,4-triazole-5-thiones react with methyl 3-chloro-2-oxo-3-phenylpropionate to give methyl 3-(2-R-5-phenylthiazol-4-yl)-7-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-6-carboxylates. According to the X-ray diffraction data, the thiazole ring in the products is planar, while the thiadiazine ring has a distorted unsymmetrical boat conformation. Depending on the substituent in the thiazole ring, methyl 3-(2-R-5-phenylthiazol-4-yl)-7-phenyl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine-6-carboxylates in crystal give rise to different supramolecular structures, lamellar and cylindrical.Translated from Zhurnal Organicheskoi Khimii, Vol. 40, No. 9, 2004, pp. 1358–1365.Original Russian Text Copyright © 2004 by Mamedov, Mustakimova, Gubaidullin, Litvinov, Levin. 相似文献
3.
Pyrolytic conversion of [1,2,4]triazino[3,4-b][1,3,4]thiadiazin-4-ones, [1,3,4]thiadiazino[2,3-b]quinazolin-10-ones and [1,2,4]triazolo[3,4-b][1,3,4]thiadiazines into their corresponding pyrazolo[5,1-c][1,2,4]triazin-4-ones, pyrazolo[4,3-b]quinazolin-9-ones and pyrazolo[5,1-b][1,2,4]triazoles via desulfurization ring contraction is described. The starting condensed 1,3,4-thiadiazines were prepared from the corresponding readily available 4-amino-3-thioxo-1,2,4-triazin-5(4H)-ones, 3-amino-2,3-dihydro-2-thioxoquinazolin-4(1H)-one and 4-amino-3(2H)-thioxo-1,2,4-triazoles upon reaction with the appropriate α-haloketones in two steps, or directly in one step in ethylpyridinium tetrafluoroborate (ionic liquid, IL). 相似文献
4.
Ricardo Bossio Stefano Marcaccini Valerio Parrini Roberto Pepino 《Journal of heterocyclic chemistry》1986,23(3):889-891
2-(2,6-Dimethylpyrimidin-4-ylaminobenzimidazole) (VIIa) and 2-(1,3,4-thiadiazol-2-ylamino)benzimidazole (VIIb) underwent a ring-closure reaction with phosgene giving 1,3-dimethyl-12H-benzirnidazo[1,2-a]pyrirnido[6,1][-d][1,3,5]triazin-12-one (IIa) and 5H-benzimidazo[1,2-a][1,3,4]thiadiazolo[2,3-d][1,3,5]triazin-5-one (IIb) two hitherto unknown heterocyclic systems. A convenient synthesis of 2,6-dimethyl-4-aminopyrimidine is described. 相似文献
5.
4H-[1,3,4]Thiadiazolo[2,3-c][1,2,4]triazin-4-ones were prepared by cyclization of 3-thio-4-amino-1,2,4-tri-azine-3,5(2H,4H)-diones with a variety of acids in the presence of concentrated sulfuric acid. The synthesis appears to be general. 相似文献
6.
Demchenko A. M. Yanchenko V. A. Lozinskii M. O. 《Russian Journal of Organic Chemistry》2003,39(7):1025-1028
Starting from 5-alkyl-4-amino-4H-1,2,4-triazole-3-thiols and substituted chloroacetanilides, the corresponding (5-alkyl-4-amino-4H-1,2,4-triazol-3-ylsulfanyl)acetanilides were synthesized. The products underwent intramolecular cyclization in boiling phosphoryl chloride to afford 3-alkyl-6-arylamino-7H-[1,2,4]-triazolo[3,4-b][1,3,4]thiadiazines. 3-Alkyl-6-aryl-7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine hydrobromides were obtained by reaction of 5-alkyl-4-amino-4H-1,2,4-triazole-3-thiols with substituted phenacyl bromides. 相似文献
7.
Yuzuru Sanemitsu Yoshinori Nakayama Masao Shiroshita 《Journal of heterocyclic chemistry》1982,19(6):1583-1584
A regioselective synthesis of 2-amino-1,2,4-triazinones ( 3a-b ) is reported, by reaction of 3-methylthio-1,2,4-triazinones ( 1a-b ) with O-(2,4-dinitrophenyl)hydroxylamine ( 2 ), as an amino transfer agent. A spectroscopic study and an unequivocal synthesis of 2-amino-4-methyl-6-phenyl-1,2,4-triazinone ( 8a ) has shown the site of amination to be N2 of the 1,2,4,-triazinone ring. Subsequent reaction of 2-amino-1,2,4-triazinone ( 3b ) with ammonium hydroxide, followed by ring closure with formic acid provided [1,2,4]triazolo[2,3-b][1,2,4]triazin-7 (1H)-one ( 10 ). 相似文献
8.
Mamdouh A. M. Taha 《Monatshefte für Chemie / Chemical Monthly》2007,138(5):505-509
Summary. Reactions of two cyclic amidrazones, the 6-methyl and 6-phenyl derivatives of 7-hydrazinotetrazolo[1,5-b][1,2,4]triazines with mono- and dicarbonyl compounds afforded various heterocyclic systems. Thus, acetic acid, benzoyl chloride,
or ethyl chloroformate reacted with the former cyclic amidrazones to yield the corresponding [1,2,4]triazolo[4,3-d]tetrazolo[1,5-b][1,2,4]triazines. With pyruvic acid or ethyl pyruvate the corresponding hydrazone derivatives were obtained, which then cyclized
to tetrazolo[1′,5′:2,3][1,2,4]triazino[5,4-c][1,2,4]triazines. The 9,10-dioxotetrazolo-triazinotriazine structures were synthesized by condensative cyclization of the
cyclic amidrazones with diethyl oxalate, whereas the reaction of these amidrazones with acetylacetone or ethyl acetoacetate
furnished pyrazolyltetrazolo[1,5-b][1,2,4]triazines through the isolable hydrazone intermediates. Some of the representative members of the prepared compounds
were screened for antimicrobial activity. 相似文献
9.
Abolghasem Davoodnia Rahele Zhiani Niloofar Tavakoli-Hoseini 《Monatshefte für Chemie / Chemical Monthly》2008,139(11):1405-1407
Starting from 1,5-dihydro-4H-pyrazolo[3,4-d]pyrimidin-4-ones, a synthesis pathway to the tricyclic pyrazolo[4,3-e][1,2,4]triazolo[4,3-c]pyrimidines is described. Reaction of 1,5-dihydro-4H-pyrazolo[3,4-d] pyrimidin-4-ones with phosphoryl chloride afforded the corresponding 4-chloro-1H-pyrazolo[3,4-d]pyrimidines. Treatment of these compounds with hydrazine hydrate at reflux temperature gave the hydrazino derivatives, which
were subsequently cyclized to the titled compounds on heating with orthoesters in ethanol.
Correspondence: Abolghasem Davoodnia, Department of Chemistry, School of Sciences, Islamic Azad University, Mashhad Branch,
Mashhad 91735-413, Iran. 相似文献
10.
Farag A. El-Essawy Ahmed F. Khattab Adel A.-H. Abdel-Rahman 《Monatshefte für Chemie / Chemical Monthly》2007,138(8):777-785
Summary. 1-Carbethoxymethyl-4,6-dimethyl-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5,7(4H,6H)-dione was synthesized and treated with hydrazine hydrate to give the corresponding hydrazide. The latter hydrazide was treated
either with phenylisothiocyanate or with carbon disulfide/alc. KOH to afford the corresponding thiosemicarbazide and oxadiazole
derivatives. Alkylation of 2-mercapto-1,3,4-oxadiazole with dimethyl sulfate or ethyl chloroacetate gave the corresponding
2-methylthio-, and 2-ethylthioglycolate derivatives. Formation of 1,3,4-thiadiazole, 5-mercapto-1,2,4-triazole, and 1,3,4-oxadiazole
were carried out by treating of the latter thiosemicarbazide with conc. H2SO4, NaOH/HCl, and HgO. Treating of 5-mercapto-1,2,4-triazole with ethyl chloroacetate afforded the thioglycolate ester. Hydrolysis
of the latter with hydrazine hydrate afforded the hydrazide derivatives. Condensation of these hydrazides with monosaccharide
aldoses gave the corresponding sugar hydrazones. The novel compounds were tested for antiviral activity against hepatitis
B virus and showed moderate activities. 相似文献
11.
E. S. Komarova V. A. Makarov L. M. Alekseeva G. V. Avramenko V. G. Granik 《Russian Chemical Bulletin》2007,56(11):2337-2343
Starting from the substituted 4,5-diaminopyrazolo[3,4-b]pyridine, derivatives of a number of tricyclic systems, viz., imidazo[4,5-d]pyrazolo[3,4-b]pyridine, pyrazolo[3,4-b][1,2,5]thiadiazolo[3,4-d]pyridine, pyrazolo[3,4-b][1,2,3]triazolo[4,5-d]pyridine, and [1,3]oxazolo[5,4-b]pyrazolo[4,3-e]pyridine, were synthesized and reaction schemes for the processes were proposed. 相似文献
12.
R. V. Tyurin E. V. Vorob’ev L. G. Minyaeva V. V. Krasnikov V. V. Mezheritskii 《Russian Journal of Organic Chemistry》2005,41(6):916-921
Formimidic acid esters derived from 1-substituted 5-aminopyrazole-4-carbonitriles reacted with carboxylic acid hydrazides on heating to give 2,7-disubstituted pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine derivatives as a result of double heterocyclization. The same compounds were obtained by thermal recyclization of 1-aroyl-2-(1-R-pyrazolo[3,4-d]pyrimidin-4-yl)hydrazines.__________Translated from Zhurnal Organicheskoi Khimii, Vol. 41, No. 6, 2005, pp. 934–938.Original Russian Text Copyright © 2005 by Tyurin, Vorob’ev, Minyaeva, Krasnikov, Mezheritskii. 相似文献
13.
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
14.
V. A. Yanchenko A. M. Demchenko M. O. Lozinskii 《Chemistry of Heterocyclic Compounds》2004,40(4):516-518
We propose a method for obtaining derivatives of 7H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazine by alkylation of 4-amino-5-methyl-4H-1,2,4-triazole-3-thiol by substituted -chloroacetanilides, followed by cyclization of the intermediate by phosphorus oxychloride. 相似文献
15.
O. A. Abd Allah 《Chemistry of Heterocyclic Compounds》2005,41(8):1076-1084
7-[1,3-Dithiolan-2-ylidene]-3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine-6,8-dione and 7-[5-oxo-1,3-dithiolan-2-ylidene]-3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo[3,4-b][1,3,4]-thiadiazepine-6,8-diones
were obtained by treating 3-phenyl-5,6,7,8-tetrahydro[1,2,4]triazolo-[3,4-b][1,3,4]thiadiazepine-6,8-diones with CS2 and chloroacetyl chloride, respectively. Treatment of the above compounds with mercaptoacetic acid gave 1,2-dibromoethane
or the corresponding spiro polyfused heterocycles. Some other triazolothiadiazepine derivatives including spiro polyfused
compounds were also synthesized.
__________
Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 8, 1256–1264, August, 2005. 相似文献
16.
The reactions of 7-chloro-9-methylthio-3-phenylpyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine (1) with some nucleophiles have been studied. Substitution of the chlorine atom with hydrogen occurs with ammonia in DMSO to give 9-methylthio-3-phenylpyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepin-7(8H)-one. With a methanolic solution of ammonia the 7-methoxy derivative is formed. Reaction of compound 1 with an excess of sodium methoxide in methanol gave 6,7-dimethoxy-9-methylthio-3-phenyl-5,6-dihydropyrimido[5,4-f][1,2,4]triazolo[3,4-b][1,3,4]thiadiazepine. The corresponding 7-substituted derivatives were obtained when compound 1 was heated with morpholine or 2-(dimethylamino)ethylamine. The azomethine bond of the thiadiazepine ring is reduced by sodium borohydride to give the corresponding 5,6-dihydro derivatives. 相似文献
17.
Piergiorgio Pecorari Marcella Rinaldi M. Paola Costi Luciano Antolini 《Journal of heterocyclic chemistry》1992,29(6):1449-1455
Derivatives of two new molecular structures, namely, 7,8-dihydro-6H,10H-[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazin-10-one and 6,7-dihydro-9H-thiazolo[3,2-a][1,2,5]thiadiazolo[3,4-d][pyrimidin-9-one, and derivatives of N-substituted sulfamic acid, namely, (8-amino-3,4-dihydro-2H,6H-pyrimido[2,1-b][1,3]thiazin-6-on-7-yl)sulfamic acid and (7-amino-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidin-5-on-6-yl)sulfamic acid, were separated out as by-products in the reduction reaction of 8-amino-3,4-dihydro-7-nitroso-2H,6H-pyrimido[2,1- b][1,3]thiazin-6-one and 7-amino-2,3-dihydro-6-nitroso-5H-thiazolo[3,2-a]pyrimidin-5-one derivatives, respectively, with sodium hydrosulfite. A mechanism of reaction, which hypothesizes the action of sodium hydrosulfite in an asymmetic form, is proposed. The results of single-crystal X-ray investigation on 7,8-dihydro-6H,10H-[1,2,5]thiadiazolo[3′,4′:4,5]pyrimido[2,1-b][1,3]thiazin-10-one (R = 0.032 for 863 reflections) and (8-amino-3,4-dihydro-2H,6H-pyrimido[2,1-b]- [1,3]thiazin-6-on-7-yl)sulfamic acid, sodium salt (R = 0.028 for 3507 reflections) are reported. 相似文献
18.
Yu. I. Gorak N. D. Obushak V. S. Matiichuk R. Z. Lytvyn 《Russian Journal of Organic Chemistry》2009,45(4):541-550
Arylation of furan-2-carboxylic acid or its methyl ester with arenediazonium chlorides in the presence of copper(II) chloride gave the corresponding 5-arylfuran-2-carboxylic acids or methyl 5-arylfuran-2-carboxylates. 5-Arylfuran-2-carbonyl chlorides reacted with potassium thiocyanate and then with 5-methyl-1,2-oxazol-3-amine to give 5-aryl-N-[3-(2-oxopropyl)-1,2,4-thiadiazol-5-yl]furan-2-carboxamides as a result of recyclization of intermediate isoxazolylthiourea derivatives. The reactions of 5-arylfuran-2-carbonyl chlorides with 5-(2-furyl)-1H-tetrazole involved opening of the tetrazole ring with elimination of nitrogen molecule and led to the formation of 2-(5-arylfuran-2-yl)-5-(2-furyl)-1,3,4-oxadiazoles. 3-Substituted 6-(5-arylfuran-2-yl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazoles were obtained by condensation of 5-arylfuran-2-carboxylic acids with 5-substituted 4-amino-4H-1,2,4-triazole-3-thiols in phosphoryl chloride. 相似文献
19.
4,8-Dimethyl-6,7,8,9-tetrahydropyrido[4′,3′:4,5]thieno[2,3-e][1,2,4]triazolo[3,4-a]-4H-pyrimidin-5-ones, 7-methyl-2,3,6,7,8,9-hexahydropyrido[4′,3′:4,5]thieno[2,3-d]pyrrolo[1,2-a]-1H, 10H-pyrimidin-10-one, 8-methyl-1,2,3,4,7,8,9,10-octahydropyrido[4′,3′:4,5]thieno[2,3-d]-11H-pyrimidin-11-one, and 9-methyl-2,3,4,5,8,9,10,11-octahydro[4′,3′:4,5]thieno[2,3-d]azepino-[1,2-a]-1H, 12H-pyrimidin-12-one which consist four new heterocyclic ring systems were synthesized from 2-amino-3-carbethoxy-5-methyl-4,5,6,7-tetrahydrothieno[2,3-c]pyridine. 相似文献
20.
Karoliina Joutsiniemi Markku Ahlgrn Pirjo Vainiotalo Olaf Morgenstem Mario Meusel 《Journal of heterocyclic chemistry》1995,32(1):283-290
The mass spectra of ten 1,3-dithioxo[1,2,4]triazolo[1,2,-b]phthalazines, five 3-iminosubstituted 1-thioxo-[1,3,4]thiadiazolo[3,4-b]phthalazines, three 3-iminosubstituted-1-thioxo[1,2,4]triazolo[1,2-b]phthalazines, and 1,3-dithioxo-5,10-dihydro[1,3,4]thiadiazolo[3,4-b]phthalazine were recorded under electron ionization. The fragmentation pathways were elucidated by metastable ion analysis and exact mass measurements. The changes in the ring-system had little effect on the fragmentation mechanism, but the effect on peak intensities was considerable. The most important fragmentations began with the opening of the triazole ring. Substituents at nitrogen atoms also had a marked effect on the mass spectral behavior. The aryl substituents prompted a whole new fragmentation. The X-ray crystal structure was determined for a few compounds. Two of the three structures of the 1,3-dithioxo[1,2,4]triazolo[1,2-b]phthalazines that were studied proved to be relatively planar, whereas the structure of 1,3-dithioxo-5,10-dihydro[1,3,4]thiadiazolo[3,4-b]phthalazine was considerably bent similarly to the 2-(4-chlorophenyl)-1,3-dithioxo-2,3,5,10-tetrahydro[1,2,4]triazolo[1,2-b]-phthalazine. The triazole and the thiadiazole rings had a strong double bond nature. 相似文献