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1.
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
2.
Nina A. Nedolya Nataly I. Schlyakhtina Lyudmila V. Klyba Igor A. Ushakov Sergei V. Fedorov Lambert Brandsma 《Tetrahedron letters》2002,43(52):9679-9681
Reaction of lithiated methoxyallene, 1-ethoxyethoxyallene, 1-(methylthio)propyne and 2-butyne with methoxymethyl isothiocyanate, MeOCH2N=C=S followed by methylation affords the imidothioates H2C=C=C(R)C(SMe)=NCH2OMe [R=Me, OMe, OCH(Me)OEt, SMe]. Rearrangement to the fully conjugated systems H2C=CH---C(R)=C(SMe)---N=CHOMe and subsequent electrocyclisation of these compounds leads to the 5-substituted 6-(methylthio)-2-methoxy-2,3-dihydropyridines with good to excellent yields. In the presence of acidic catalysts or by heating at elevated temperatures these dihydropyridines eliminate methanol to afford 3-substituted 2-(methylthio)pyridines. The aroma compound 2-(methylthio)-3-pyridinol was obtained by acid-catalysed treatment of 3-(1-ethoxyethoxy)-2-(methylthio)pyridine. 相似文献
3.
L. V. Klyba N. A. Nedolya O. A. Tarasova E. R. Zhanchipova O. G. Volostnykh 《Russian Journal of Organic Chemistry》2010,46(2):218-225
Mass spectra were investigated for the first time of four structural isomers of heterocycles, formerly inavailable 7-methyl-2-(methylsulfanyl)-3-(1-ethoxyethoxy)-4,5-dihydro-3H-azepine, 2,2-dimethyl-6-(methylsulfanyl)-5-(1-ethoxyethoxy)-2,3-dihydropyridine, 1-isopropyl-2-(methylsulfanyl)-3-(1-ethoxyethoxy)pyrrole,
and N-isopropyl-N-methyl-3-(1-ethoxyethoxy)-2-thiophenamine prepared from a single linear precursor, adduct of α-lithiated 1-(1-ethoxyethoxy)allene
and isopropyl isothiocyanate. All compounds formed a molecular ion (I
rel
1–6%) whose primary fragmentation at the electron impact (70 eV) occurs in two principal directions related to the cleavage
of the C-O bonds in the 1-ethoxyethoxy-substituent: with a simple rupture of the bonds C-OEt and C-O(heterocycle) and with
the elimination of an ethoxyethene molecule. In the spectra of 4,5-dihydro-3H-azepine and 2,3-dihydropyridine the first fragmentation
channel of [M]+· dominates. The second direction prevailes at the fragmentation of pyrrole and thiophene molecular ions leading to an odd-electrons
ion with m/z 171. Further fragmentation of this ion is characteristic of each isomer and resulted in the formation of diagnostic
ions providing a possibility of identification of these isomers by mass spectrometry. 相似文献
4.
The reactions of substituted 3-cyanopyridine-2(1H)-thiones and 3-cyano-2-(methylthio)pyridines with lithium aluminum hydride in anhydrous diethyl ether afforded the corresponding 3-aminomethyl derivatives, which were used in the synthesis of the corresponding amides. 相似文献
5.
Syntheses of 2,5-bis(4-methyl-2-thienyl)thiophene 3 and 2,5-bis(4-methyl-2-thienyl)pyrrole 4 are described. The key step involves Stetter reaction between 4-methyl-2-thiophenecarboxaldehyde and divinyl sulfone. Cyclizaton of the resulting 1,4-bis-(4-methyl-2-thienyl)-1,4-butanedione 2 with Lawesson's reagent gives 2,5-bis(4-methyl-2-thienyl)thiophene 3, whereas condensation with ammonium acetate provides the 2,5-bis(4-methyl-2-thienyl)pyrrole 4. 相似文献
6.
Unlike 1-aminobenzimidazoles, 1-alkylaminobenzimidazoles are thiolated on fusing with sulfur without elimination of theN-amino group, yielding the previously unknown 1-(alkylamino)benzimidazoline-2-thiones. These compounds can be more conveniently obtained on a preparative scale by thiolation of 1-alkylacetamidobenzimidazoles with subsequent hydrolytic elimination of the acetyl group. When 1-(dialkylamino)benzimidazoles are fused with sulfur, they are converted into 1-(dialkylamino)benzimidazoline-2-thiones. By alkylation of 1-(methylamino)- and 1-(diethylamino)benzimidazoline-2-thiones with methyl iodide in alkaline media the corresponding 2-(methylthio)benzimidazoles were prepared.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2231–2235, November, 1995.The authors are grateful to the Contest Center of Basic Natural Science at St. Petersburg University for financial support of this study. 相似文献
7.
The corresponding 1-(2-quinoxalyl)-, 1-[3,5-di(trifluoromethyl)phenyl]-, and 1-ethoxycarbonyl-3-methyl-4-oxo-4,5,6,7-tetrahydroindazoles have been obtained from reactions of 2-acetyl-1,3-cyclohexanedione, its 5,5-dimethyl and 5-(2-furyl) derivatives, with 2-hydrazinoquinoxaline, 3,5-di(trifluoromethyl)phenylhydrazine, and ethoxycarbonylhydrazine. On interaction with ethoxycarbonylhydrazine the intermediate 2-[1-(-ethoxycarbonyl)hydrazino]ethylidene-1,3-cyclohexanediones were also isolated. From the potassium salt of 2-formyldimedone and 2-carboxyphenylhydrazine hydrochloride, 2-(2-carboxyphenyl)hydrazinomethylene-5,5-dimethyl-1,3-cyclohexanedione was obtained, the cyclization of which in ethanol in the presence of HCl led to 1-(2-carboxyphenyl)- and 1-(2-ethoxycarbonylphenyl)-6,6-dimethyl-4-oxo-4,5,6,7-tetrahydroindazole. 相似文献
8.
Ana Filipa L.O.M. Santos Manuel A.V. Ribeiro da Silva 《The Journal of chemical thermodynamics》2010,42(12):1441-1450
The standard molar enthalpies of formation, in the crystalline phase, of three halogenated 1-phenylpyrrole derivatives, namely 1-(4-fluorophenyl)pyrrole, 1-(4-chlorophenyl)pyrrole, and 1-(4-iodophenyl)pyrrole were derived from the respective enthalpies of combustion, measured by rotating-bomb combustion calorimetry. Their enthalpies of sublimation, at T = 298.15 K, were obtained from the Knudsen mass-loss effusion technique. From these two experimental parameters, the standard molar enthalpies of formation, in the gaseous phase, at T = 298.15 K, of 1-(4-fluorophenyl)pyrrole, 1-(4-chlorophenyl)pyrrole, and 1-(4-iodophenyl)pyrrole were calculated, respectively, as (26.2 ± 2.4) kJ · mol−1, (196.2 ± 2.5) kJ · mol−1, and (311.5 ± 2.4) kJ · mol−1.The gas-phase enthalpies of formation of both fluorine and chlorine compounds were estimated by G3(MP2)//B3LYP computations. For the iodine compound, the B3LYP/6-311G(d):ECP46MDF approach was employed. Additionally, the DFT calculations were extended to estimate the enthalpy of formation of the bromine derivative, 1-(4-bromophenyl)pyrrole, performed at the B3LYP/6-311G(d) level of theory. 相似文献
9.
A synthesis of novel derivatives of 6-methyluracil, 6-methyl-2-thioxo-, and 2-imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one
containing a 2-(phenoxy)ethyl substituent at position 5 of the pyrimidine ring has been carried out. It was found that 5-[2-(phenoxy)ethyl]
derivatives of 6-methyl-2-thioxo- and 2-imino-6-methyl-2,3-dihydro-1H-pyrimidin-4-one are obtained by the condensation of
the corresponding ethyl 3-oxo-2-(2-phenoxyethyl)butanoates with thiourea or guanidine. 6-Methyl-5-[2-(phenoxy)ethyl]uracils
can be prepared by treating 6-methyl-5-[2-(phenoxy)ethyl]-2-thioxo-2,3-dihydro-1H-pyrimidin-4-ones with an excess of aqueous
monochloroacetic acid solution.
__________
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1213–1217, August, 2005. 相似文献
10.
Shubhangi C. Joshi Kunjbihari N. Trivedi 《Monatshefte für Chemie / Chemical Monthly》1992,123(6-7):557-564
Summary The Claisen rearrangement of 7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 a) gave 7-hydroxy-8-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (3 a) and 2,3-dihydro-2,6-diphenyl-3-methyl-(7H)furo[2,3-h]-1-benzopyran-7-one (7 a). 2-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (2 b) afforded4 b and7 b. 8-Methyl-7-(3-phenyl-2-propenyloxy)-3-phenyl-(4H)-1-benzopyran-4-one (12) gave only the alkali soluble product 7-hydroxy-8-methyl-6-(1-phenyl-2-propenyl)-3-phenyl-(4H)-1-benzopyran-4-one (13).3 a,4 b, and13 were further cyclized in acidic medium to9 a,10 b, and14 followed by dehydrogenation.This paper is dedicated to Dr. F. M. Dean, Department of Organic Chemistry, Robert Robinson Laboratories, University of Liverpool, Liverpool, U. K., on his retirement 相似文献
11.
Reaction of 3,6-diphenyl-, 3,6-bis(2-pyridyl)- and the unsubstituted 1,2,4,5-tetrazine with 4,5-dihydro-1-methyl-2-(methylthio)pyrrole ( 2 ) and 1-raethyl-2-(methylthio)-4.5,6,7-tetrahydroazepine ( 3 ) gives 4,7-di-R-2,3-dihydro-1-methylpyrrolo[2,3-d]pyridazine ( 4 , R = phenyl, 2-pyridyl, hydrogen) and 6,9-di-R-1-methyl-2,3,4,5-tetrahydropyridazino[4,5-6]azepine ( 5 ), R = phenyl, 2-pyridyl, hydrogen), respectively, in reasonable to good yields. The compounds 4 (R = phenyl, hydrogen) are converted into their corresponding 1-methylpyrrolo-[2,3-d]pyridazines 6 by reaction with potassium permanganate in butanone. Reaction of 3-phenyl-1,2,4,5-te-trazine with 2 and 3 leads to the exclusive formation of the 7-phenyl isomer 4d and 9-phenyl isomer 5d , respectively, indicating that the cycloaddition is regiospecific. The mechanism is discussed. 相似文献
12.
Shynggys Sergazy Zarina Shulgau Aigerim Zhulikeyeva Yerlan Ramankulov Irina V. Palamarchuk Ivan V. Kulakov 《Molecules (Basel, Switzerland)》2022,27(17)
Currently, studies are being conducted on the possible role of the cytoprotective effect of biologically active substances in conditions of cerebral hypoxia or cardiomyopathies. At the same time, oxidative stress is considered one of the important mechanisms of cellular cytotoxicity and a target for the action of cytoprotectors. The aim of this study is to search for derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones. The probability of cytoprotective action was assessed by measuring cell viability using two tests (with neutral red dye and MTT test). It was found that some derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones under the conditions of our experiment had a pronounced cytoprotective activity, providing better cell survival in vitro, including the MTT test and conditions of blood hyperviscosity. To correlate the obtained results in vitro, molecular docking of the synthesized derivatives was also carried out. The standard drug omeprazole (co-crystallized with the enzyme) was used as a standard. It was shown that all synthesized derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones had higher affinity for the selected protein than the standard gastro-cytoprotector omeprazole. The studied derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones also fully satisfy Lipinski’s rule of five (RO5), which increases their chances for possible use as orally active drugs with good absorption ability and moderate lipophilicity. Thus, the results obtained make it possible to evaluate derivatives of 3-(arylmethylamino)-6-methyl-4-phenylpyridin-2(1H)-ones as having a relatively high cytoprotective potential. 相似文献
13.
Kushvar Hajiyeva Arif Ismiev Max Franz Marc Schmidtmann Jürgen Martens Abel Maharramov 《合成通讯》2017,47(22):2031-2035
A series of polyfunctionalized 2-amino-1-methyl-6-(methylthio)-5-nitro-4-aryl-1,4-dihydropyridine-3-carbonitriles have been prepared using a multicomponent condensation reaction between aromatic aldehydes, malononitrile, and (Z) N-methyl-1-(methylthio)-2-nitroethenamine in the presence of Et3N in acetonitrile. 相似文献
14.
G. D. Gamalevich A. V. Ignatenko E. P. Serebryakov N. E. Voishvillo 《Russian Chemical Bulletin》1995,44(4):743-748
With a view to obtaining both enantiomers of 3-(4-methoxycarbonyl)phenyl-2-methyl-1-propanols, (R)-1 and (S)-1, from the respective racemate, (±)-1, the hydrolysis of its acetate, (±)-2, in the presence of porcine pancreatic lipase (PPL) has been studied. The optical puriry of (R)-1 and (S)-1 thus obtained was unsatisfactory (ee 22–27%), and could not be increased beyondee 33% by repeated enzymatic hydrolysis of the unconverted fraction of the acetate. In contrast with this, the biohydrogenation of 3-(4-methoxycarbonyl)phenyl-2-methyl-2-propen-1-ol (4) with fermentingSaccharomyces cerevisiae afforded (S)-1 of considerably higher optical purity (ee 41–90 %, depending on the strain). The stereochemical correlation of the products obtained in the two biochemical processes under study shows that the PPL-catalyzed hydrolysis of (±)-2 produces preferably (R)-1.Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 4, pp. 761–766, April, 1995.The authors express their gratitude to the Russian Foundation for Basic Research for financial support (Grant No. 93-03-5893). 相似文献
15.
Convenient and Regiospecific Method for Synthesis of 4,5-Diaryl-1-methyl-2-(methylthio)-1H-imidazole
A convenient, high-yielding, regiospecific synthesis of 1H-imidazole-2-thiones ring has been developed. In addition, a series of 4,5-diaryl-1-methyl-2-(methylthio)-1H-imidazoles 8 were synthesized and characterized. The structure of regioisomers was confirmed through nuclear Overhauser effect spectroscopy and NMR spectroscopy. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications® to view the free supplemental file. 相似文献
16.
The geometric parameters, the charge distribution, and the energetics of N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)-and N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimides and their conjugated acids were studied by density functional theory calculations
at the B3LYP/6-31G(d) level. The mechanism of the tandem hydride transfer/cyclization sequence, which occurs after protonation
of N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)-and N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimides, was analyzed. The investigation of the potential energy surface for the tandem hydride
transfer/cyclization of the iminium cation that formed upon protonation revealed that the hydride transfer followed by intramolecular
cyclization at position 7 of the indole fragment in N-methyl-2-(N-ethylanilino)-3-(indol-1-yl)maleimide is the preferable process, unlike alternative intramolecular cyclization involving
the cationic center at the C(2) atom of the indole fragment and the benzene ring of the N-ethylaniline fragment of the indoleninium cation in N-methyl-2-(N-ethylanilino)-3-(indol-3-yl)maleimide. A study of the key intermediates of the assumed reaction mechanism demonstrated that
these intermediates are actually stationary points on the potential energy surface (minima and transition states).
Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2069–2073, December, 2006. 相似文献
17.
Summary 3(Bis(alkylthio)methylene)-3H-isobenzofuran-1-ones2a–e and 2-(bis(alkylthio)methylene)-3(2H)-benzofuranone derivatives4a–c are obtained by reaction of phthalides1a–d or 3(2H)-benzofuranone (coumaranone3), respectively, with carbon disulfide under basic conditions followed by alkylation. The reaction behaviour of the new compounds2 and4 is investigated. 2-((2-Dimethylthio-1-oxo)ethyl)benzoic acid N,N-dimethylamide (7a) and 2-((2-dimethylthio-1-oxo)ethyl)-benzoic acid 2-methylpiperidide (7b) are surprisingly formed instead of the methylthio substitution products by treatment of2a with the corresponding amine in the presence of aluminum chloride.
Herrn Professor Dr. Dr. h. c.Waldemar Adam zum 60. Geburtstag gewidmet 相似文献
18.
N-[1-Hydroxyimino-2-methyl-1-(2-pyridyl)prop-2-yl]hydroxylamine, a new representative of the series of α-hydroxylamino oximes,
was synthesized. Based on this compounds, 3-imidazoline 3-oxide and 2-imidazoline 3-oxide derivatives, were obtained, and
some of their chemical properties were investigated.
Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 1, pp. 131–136, January, 1997. 相似文献
19.
A simple and ecofriendly protocol has been developed for the expedient synthesis of novel dihydroindeno[1,2-b]pyrrol-4(3aH)-ones from the reaction of ninhydrin and (E)-N-methyl-1-(methylthio)-2-nitroethenamine or (E)-N-(1-(methylthio)-2-nitrovinyl)anilines. 相似文献
20.
N. N. Chipanina Z. V. Stepanova G. A. Gavrilova L. N. Sobenina A. I. Mikhaleva 《Russian Chemical Bulletin》2000,49(11):1914-1916
5-Phenyl-2-(1-phenyl-2-trichloroacetylethenyl)pyrrole was synthesized by the reaction of 2-phenylpyrrole with 1-phenyl-2-trichloroacetylacetylene
on silicon oxide. The structure of an intramolecular proton-transfer H-complex was assigned to the title compound based on
analysis of its IR spectra in solutions in the temperature range of 165–298 K.
Published inIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 1945–1947, November, 2000. 相似文献