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1.
Previously it was shown that condensation of dimethyl N-cyanodithioimidocarbonate ( 1a ) with methylhydrazine gave predominantly 1-methyl-5-methylthio-1H-,2,4-triazol-3-amine ( 2 ), which was initially identified erroneously as the regioisomer l-methyl-3-methylthio-1H-1,2,4-triazol-5-amine ( 3 ). We have found that reaction of dimethyl N-cyanoimidocarbonate ( 1b ) with methyl hydrazine affords a high yield of 3-methoxy-1-methyl-1H-1,2,4-triazol-5-amine ( 4 ) rather than the regioisomer 5-methoxy-1-methyl-1H-1,2,4-triazol-3-amine ( 5 ). The structure assignment of 4 was confirmed by X-ray crystallographic analysis of the benzenesulfonyl isocyanate adduct 7 . Triazole 5 was obtained after reacting dimethyl N-cyanothioimidocarbonate ( 1c ) with methylhydrazine. 相似文献
2.
V. L. Gein V. V. Mishunin E. P. Tsyplyakova M. I. Vakhrin P. A. Slepukhin 《Russian Journal of Organic Chemistry》2011,47(7):1077-1082
Fusion of methyl 4-(2-thienyl)-2,4-dioxobutanoate with 1H-tetrazol-5-amine monohydrate and aromatic aldehyde gave methyl 7-aryl-6-(2-thenoyl)-4,7-dihydrotetrazolo[1,5-a]pyrimidine-5-carboxylates which reacted with an equimolar amount of hydrazine hydrate at 180–190°C under solvent-free conditions
to produce 9-aryl-8-(2-thienyl)-4,9-dihydrotetrazolo[1′,5′: 1,2]pyrimido[4,5-d]pyridazin-5(6H)-ones. 相似文献
3.
Timothy A. Riley William J. Hennen N. Kent Dalley Bruce E. Wilson Roland K. Robins 《Journal of heterocyclic chemistry》1986,23(6):1709-1714
The synthesis of the first [1,3,5]triazine carbon linked nucleosides are reported. 4-Amino-6-(β-D-ribofuranosyl)[1,3,5]triazin-2(1H)-one ( 8 ), an analog of 5-azacytidine and pseudoisocytidine was prepared. 2,5-Anhydro-D-allonamidine hydrochloride ( 3 ) was condensed with dimethyl cyanoiminodithiocarbonate ( 4 ) to give 4-methylthio-6-(β-D-ribofuranosyl)[1,3,5]triazin-2-amine ( 5 ). Compound 5 was reacted with m-chloroperbenzoic acid to give 4-methylsulfinyl-6-(β-D-ribofuranosyl)[1,3,5]triazin-2-amine ( 6 ). Displacement of the methyl sulfinyl with the appropriate nucleophile gave 6-(β-D-ribofuranosyl)[1,3,5]triazine-2,4-diamine ( 7 ), 4-amino-6-(β-D-ribofuranosyl)[1,3,5]triazin-2(1H)-one ( 8 ), and 4-amino-6-(β-D-ribofuranosyl)[1,3,5]triazine-2(1H)-thione ( 9 ). Dethiation of compound 5 with Raney nickel gave 4-(β-D-ribofuranosyl)[1,3,5]triazin-2-amine ( 10 ). The crystal structure of 7 was determined by single crystal X-ray. 相似文献
4.
Three-component condensation of quinolin-5-amine with methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate and aromatic
(heteroaromatic) aldehydes or cyclohex-3-ene-1-carbaldehyde gave previously unknown 1,7-phenanthroline derivatives. The reactions
in butan-1ol were characterized by 100% regioselectivity but low stereoselectivity, and mixtures of cis- and trans-isomeric methyl 7-aryl(hetaryl, cyclohexenyl)-10,10-dimethyl-8-oxo-7,8,9,10,11,12-hexahydrobenzo[b][1,7]phenanthroline-9-carboxylates were obtained at a ratio of ∼45: 55. 相似文献
5.
A. L. Kurlovich V. A. Tarasevich N. G. Kozlov 《Russian Journal of Organic Chemistry》2009,45(10):1503-1508
Condensation of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and cyclohexane-1,3-dione, methyl
2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone gave the corresponding 7-(2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydro-12H-benzo[c]acridin-8-ones. The reaction of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde with naphthalen-1-amine and indan-1,3-dione
produced 7-(2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-8H-benzo[h]indeno[1,2-b]quinolin-8-one. 7-(2′-Hydroxy-1,1′: 3′,1″-terphenyl-5′-yl)-7,8,9,10,11,12-hexahydrobenzo[b][1,10]phenanthrolin-8-ones were obtained by three-component condensation of 2′-hydroxy-1,1′: 3′,1″-terphenyl-5′-carbaldehyde
with quinolin-8-amine and cyclohexane-1,3-dione, methyl 2,2-dimethyl-4,6-dioxocyclohexane-1-carboxylate, or dimedone. 相似文献
6.
N. A. Nedolya O. A. Tarasova O. G. Volostnykh A. I. Albanov B. A. Trofimov 《Chemistry of Heterocyclic Compounds》2012,47(11):1430-1435
For the case of 1-(allylsulfanyl)-2-methoxy-N-(1-methylethylidene)buta-1,3-dien-1-amine, obtained from α-lithiated methoxyallene, isopropyl isothiocyanate, and allyl bromide,
it was shown that 5-ethylidene-2-(1-methoxyprop-2-enyl)-4,4-dimethyl-4,5-dihydro-1,3-thiazole and 6-methoxy-2-methyl-3H-azepine
are formed competitively upon the action of the t-BuOK–THF–DMSO system. 相似文献
7.
James L. Kelley Ed W. Mclean Ronda G. Davis Ronald Crouch 《Journal of heterocyclic chemistry》1990,27(6):1821-1824
6-[[(Hydroxyimino)phenyl]methyl]-1-[(1-methylethyl)sulfonyl]-1H-imidazo[4,5-b]pyridin-2-amine ( 1 ), an aza analogue of enviroxime, was synthesized in eight steps from 6-hydroxynicotinic acid ( 2 ). Acid 2 was nitrated, chlorinated with phosphorus pentachloride, and subjected to Friedel-Crafts aroylation to give 6-chloro-5-nitro-3-pyridyl phenyl ketone ( 5 ). Amination of 5 was followed by reduction of the nitro group and condensation with ethoxycarbonylisothiocyanate to give 6-benzyl-2-ethoxycarbonylamino-1H-imidazo[4,5-d]pyridine ( 8 ). The ethoxycarbonyl moiety of 8 was cleaved, N-1 was isopropylsulfonylated, and the carbonyl moiety was condensed with hydroxylamine to give 1 . Compound 1 was inactive against rhinovirus 1B and poliovirus type 1 . 相似文献
8.
L. M. Potikha V. A. Kovtunenko A. V. Turov G. V. Palamarchuk R. I. Zubatyuk O. V. Shishkin 《Chemistry of Heterocyclic Compounds》2009,45(3):327-335
The direction of the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one (γ-bromodypnone) with hydrazines depends on the nature
of the substituent they contain. Reaction with 1-methylhydrazinium hydrosulfate gives 1-methyl-3,5-diphenylpyridazin-1-ium
bromide but carboxylic acid hydrazides give N-(2,4-diphenyl-1H-pyrrol-1-yl)carboxylic acid amides. γ-Bromodypnone and phenylhydrazine
give both 1,3,5-triphenyl-1,4-dihydropyridazine and N,2,4-triphenyl-1H-pyrrol-1-amine (15%). 1-(2,4-Dinitrophenyl)hydrazine
gives the 2,4-dinitrophenylhydrazone of (Z)-4-bromo-1,3-diphenyl-2-buten-1-one. Condensation of 2,4-diphenyl-1H-pyrrol-1-amine
with aromatic aldehydes readily leads to N-(arylmethylidene)-2,4-diphenyl-1H-pyrrol-1-amines and alkylation with methyl iodide
gives N,N-dimethyl-2,4-diphenyl-1H-pyrrol-1-amine.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 404–414, March, 2009. 相似文献
9.
Yifan Ji Li Li Guangzhou Zhu Ya Zhou Xinchi Lu Wenjing He Lijiu Gao Liangce Rong 《Journal of heterocyclic chemistry》2020,57(4):1781-1796
The efficient and novel method for the synthesis of pyrazolo[3,4-b]pyridine and pyrano[2,3-c]pyrazole derivatives from the multicomponent reaction of aromatic aldehydes (isatins), N-methyl-1-(methylthio)-2-nitroethen-1-amine, and 3-aminopyrazole or methyl 3-hydroxy-1H-pyrazole-5-carboxylate under normal laboratory conditions was reported in this research. The advantages of this research are wide range of substrates, high yields, and simple operation. 相似文献
10.
V. R. Akhmetova Z. T. Niatshina Z. A. Starikova L. F. Korzhova A. G. Ibragimov 《Russian Journal of Organic Chemistry》2011,47(6):920-927
Thiomethylation of heteroaromatic amines with formaldehyde-hydrogen sulfide gave linear and cyclic heteroatom compounds: N,N′-[methylenebis(sulfanediylmethylene)]bishetarenamines and 5-hetaryl-1,3,5-dithiazinanes. N,N′-[Methylenebis(sulfanediylmethylene)]bishetarenamines were found to undergo transformation into 5-hetaryl-1,3,5-dithiazinanes
by the action of CH2O-H2S. Transamination of 5-methyl-1Hpyrazol-3-amine, 6-nitro-1,3-benzothiazol-2-amine, and 5-bromopyridin-2-amine with 5-methyl-1,3,5-dithiazinane selectively
afforded the corresponding 5-hetaryl-1,3,5-dithiazinanes. 相似文献
11.
We have observed unusual thermal rearrangements of N-cyclohexylidene-4-methyl-1-(methylthio)penta-1,3-dien-1-amine to 4,4-dimethyl-2-(methylthio)-3,3a,4,4a,5,6,7,8-octahydrobenzo[4,1]cyclobuta-[1,2-b]pyrrole and 1-cyclohexyl-5-methylpyridine-2(1H)-thione. 相似文献
12.
M. Judith Percino Víctor M. Chapela Omar Urzúa Ling-Fa Montiel Cecilia Rodríguez-Barbarín 《Research on Chemical Intermediates》2007,33(7):623-629
The novel intermediate 1-(p-fluorophenyl)-2-(2′-pyridyl)ethanol or 2-[2′-(1-hydroxy-1-(p-fluorophenyl)ethyl]pyridine and the corresponding novel dehydration compound 1-(p-fluorophenyl)-2-(2′-pyridyl)ethene or 2-[p-fluorophenylvinyl]pyridine were obtained from the condensation reaction of p-fluorophenylaldehyde and 2-picoline under catalyst-and solvent-free conditions. The intermediate 1-(p-fluorophenyl)-2-(2′-pyridyl)ethanol was obtained at 42 h reaction time and temperature of 120°C, respectively. 1H-NMR, IR spectroscopic data of the 1-(p-fluorophenyl)-2-(2-pyridyl)ethanol clearly showed the presence of the-CH2-CHOH-group. The compound was obtained as a white powder with m.p. 121–122°C and a yield of 8%. For 1-(p-fluorophenyl)-2-(2-pyridyl)ethene, the reaction conditions were similar, but the reaction temperature was increased to yield
the double bond in the 1-(p-fluorophenyl)-2-(2′-pyridyl)ethene. At the reaction temperature of 140°C, the compound was a slightly brown powder with a
m.p. of 78°C and yield of 18%. 1H-NMR, IR spectroscopic data for the 1-(p-fluorophenyl)-2-(2′-pyridyl)ethene showed the presence of a double bond in trans configuration (-CH=CH-), characteristic of a styrylpyridine. 相似文献
13.
An efficient method has been developed for the synthesis of 2-[3(5)-aryl(methyl)pyrazol-4-yl]-1H-benzimidazoles by cyclocondensation
of 2-acylmethyl-1H-benzimidazoles benzoylhydrazones with DMF dimethylacetal. The tautomerism of the compounds obtained via
migrations of a proton between the pyrazole nitrogen atoms has been studied by 1H NMR. The more stable tautomers have electron acceptor aryl substituents placed at position 3 of the pyrazole ring and electron
donor aryl substituents or a methyl at position 5.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1370–1377, September, 2006. 相似文献
14.
《Monatshefte für Chemie / Chemical Monthly》2003,21(1):909-927
Various routes for an effective synthesis of 1,6,7,11b-tetrahydro-2H-pyrimido[4,3-a]isoquinolin-4-amine and its 9-methoxy derivative, which were designed as tricyclic triaza-analogues with stable positive charge to mimic carbocationic high energy intermediates (HEI) of the ergosterol biosynthesis, were investigated. Starting from β-phenylethylamines the corresponding 3-chloro-N-phenethylpropionamides were prepared and transformed into N-phenethyl-3-phthalimidopropionamides. These amides were cyclized via Bischler-Napieralski reaction to yield after hydrolytic deprotection 1-(aminoethyl)tetrahydroisoquinolines. The 1,6,7,11b-tetrahydro-2H-pyrimido[4,3-a]isoquinoline ring system was then built up by condensation of the bicyclic diamines with various carbonic acid derivatives (carbon disulfide, nitroguanidine, tetraethyl orthocarbonate). Along with the applied reaction sequences unexpected side reactions took place. The structures of all isolated compounds were proven and completely assigned on the basis of homo- and heteronuclear correlated 1D and 2D NMR experiments. The in vitro antifungal susceptibility tests with a standard panel of eight pathogenic fungi revealed only weak antimycotic effects of the pyrimidoisoquinolinamine salts, but strong inhibitory activity of the intermediate 1-(aminoethyl)-3,4-dihydroisoquinoline. 相似文献
15.
The revised structure of the indole alkaloid aristolasicone ( 2 ) was confirmed through a convergent total synthesis of the racemic form of this metabolite. The key step involves a one-pot condensation/cyclization reaction between 1-(4-methoxyphenylsulfonyl)-1H-indole-2-acetaldehyde ( 9 ) and (±)-trans-5-(2,6-difluorobenzyloxy)-p-menth-l-en-8-amine ((±)-7). The resulting allohobartine derivative (±)- 13 , obtained in 84% yield, was deprotected and oxidized to (±)-alloscrratenone ((±)- 15 ) which cyclized smoothly to the target molecule (±)-2 upon exposure to BF3 · Et2O. 相似文献
16.
Ichizo Okabayashi Noriko Murakami Kaoru Sekiya 《Journal of heterocyclic chemistry》1989,26(3):635-637
1, 5-Dichloro-9H-thioxanthen-9-one ( 2 ) was prepared by cyclization of 2-chloro-6-[(2-chlorophenyl)thio]-benzoic acid ( 10 ) obtained from 2-chloro-6-iodobenzoic acid ( 9 ) and 2-chlorobenzenethiol. Similarly, 1, 7-di-chloro-9H-thioxanthen-9-one ( 6 ) was prepared from 9 via 2-chloro-6-[(4-chlorophenyl)thio]benzoic acid ( 11 ). Compound 6 was also obtained by condensation of 2-chloro-6-mercaptobenzoic acid ( 12 ) with chlorobenzene in the presence of sulfuric acid. 相似文献
17.
A. N. Pyrko 《Russian Journal of Organic Chemistry》2010,46(12):1843-1847
Three-component condensation of naphthalen-1-amine with triethyl orthoformate and dimedone or cyclopentane-1,3-dione, as well
as the reaction of naphthalen-1-amine with 2-acetyl-5,5-dimethylcyclohexane-1,3-dione, gave the corresponding 2-[1-(α-naphthylamino)alkylidene]cycloalkane-1,3-diones
which underwent intramolecular cyclization to 7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one derivatives on heating in polyphosphoric acid. 9,9-Dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-one was reduced to 9,9-dimethyl-7,8,9,10-tetrahydrobenzo[c]phenanthridin-7-ol with sodium tetrahydridoborate. 相似文献
18.
《Monatshefte für Chemie / Chemical Monthly》2003,134(6):909-927
Summary. Various routes for an effective synthesis of 1,6,7,11b-tetrahydro-2H-pyrimido[4,3-a]isoquinolin-4-amine and its 9-methoxy derivative, which were designed as tricyclic triaza-analogues with stable positive
charge to mimic carbocationic high energy intermediates (HEI) of the ergosterol biosynthesis, were investigated. Starting
from β-phenylethylamines the corresponding 3-chloro-N-phenethylpropionamides were prepared and transformed into N-phenethyl-3-phthalimidopropionamides. These amides were cyclized via Bischler-Napieralski reaction to yield after hydrolytic deprotection 1-(aminoethyl)tetrahydroisoquinolines. The 1,6,7,11b-tetrahydro-2H-pyrimido[4,3-a]isoquinoline ring system was then built up by condensation of the bicyclic diamines with various carbonic acid derivatives
(carbon disulfide, nitroguanidine, tetraethyl orthocarbonate). Along with the applied reaction sequences unexpected side reactions
took place. The structures of all isolated compounds were proven and completely assigned on the basis of homo- and heteronuclear
correlated 1D and 2D NMR experiments. The in vitro antifungal susceptibility tests with a standard panel of eight pathogenic fungi revealed only weak antimycotic effects of
the pyrimidoisoquinolinamine salts, but strong inhibitory activity of the intermediate 1-(aminoethyl)-3,4-dihydroisoquinoline.
Corresponding author. E-mail: edith.goessnitzer@uni-graz.at
Received August 26, 2002; accepted September 2, 2002
Published online February 3, 2003 相似文献
19.
S. I. Orysyk L. N. Rybachuk V. I. Pekhnyo V. V. Orysyk 《Russian Journal of Inorganic Chemistry》2011,56(11):1747-1751
New Pd(II) complexes with 1-allyl-3-(2-pyridyl)thiourea (APTU) of the formulas [Pd(C9H11N3S)Cl2] (I) and [Pd(C9H11N3S)2]Cl2 (II) were obtained and examined by UV-Vis, IR, and 1H NMR spectroscopy. The conditions for the complexation reactions were optimized.
The instability constants and molar absorption coefficients of these complexes were calculated. Comparison of the characteristic
bands in the UV-Vis and IR spectra of the complexes and free APTU revealed that the ligand in both complexes is coordinated
to the metal atom in the thione form in the bidentate chelating mode through the S atom of the thiourea group and the pyridine
N atom. In the UV-Vis spectra of the complexes, the charge transfer bands (π → π* Py) and n → π* (C=NPy), (C=S) experience hypsochromic shifts by 450–470 cm−1 caused by the coordination of APTU to the metal ion, which gives rise to ligand-metal charge-transfer bands (C=NPy → Pd, n → π* (C=S)) and (SPd). The protons in the 6-, 4-, and 3-positions of the pyridine ring and the thiourea NH proton in the
chelate ring are most sensitive to the complexation. 相似文献
20.
G. N. Rozentsveig V. Yu. Serykh K. A. Chernyshev I. B. Rozentsveig G. G. Levkovskaya L. B. Krivdin 《Russian Journal of Organic Chemistry》2011,47(4):572-576
4-Chloro-N-[2,2-dichloro-1-(4-methoxyphenyl)-2-phenylethyl]benzenesulfonamide reacted with thiourea on heating in DMF in the presence
of sodium carbonate to give 5-(4-methoxyphenyl)-4-phenyl-1,3-thiazole-2-amine. A probable reaction scheme includes cyclization
of the initial N-dichloroethyl amide to N-sulfonyl-2,3-diaryl-2-chloroaziridine which undergoes isomerization with opening of the three-membered ring to 1-arylsulfonylamino-2-chloro-2-(4-methoxyphenyl)-1-phenylethene.
The subsequent heterocyclization in the reaction with thiourea is accompanied by aromatization via elimination of the arenesulfonamide
fragment. 相似文献