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1.
Utility and limitation of the title reaction was studied. When (E)-3-(4-t-butyl- and 4-phenylcyclohex-1-en-1-yl)-2-(trimethylsilylmethyl)prop-2-en-1-ols were treated with Ms2O or MsCl, 3-t-butyl- and 3-phenyl-8-methylbicyclo[4.3.0]nona-1(6),7-dienes were obtained, respectively. The corresponding (Z)-isomer afforded a complex mixture, among which an elimination product was detected. (E)-4-(4-t-Butylcyclohexylidene)-2-(trimethylsilylmethyl)but-2-en-1-ol afforded only elimination product. 相似文献
2.
《Tetrahedron》2003,59(7):1021-1032
The conjugate (E)- and (Z)-(4′-pyridylethenyl)-4-phenylethyne (E-4 and Z-4) has been satisfactorily prepared by two different routes: (a) by dehydrohalogenation of 4′-pyridylethenyl-4-phenyl-β-chloroethene; (b) by the Wittig reaction between p-(iodobenzyl)(triphenyl)phosphine ylide and 4-pyridinecarboxaldehyde, E/Z isomer separation, and cross-coupling with 2-methyl-but-3-yn-2-ol followed the propanone elimination. The Glaser oxidative dimerization of (Z)-4 yields (Z,Z)-1,4-di[(4′-pyridylethenyl)-4-phenyl]-buta-1,3-diyne in good yield, (Z,Z)-5. (E,E)-5 was obtained by phase transfer oxidative dimerisation of (E)-4 in presence of their N-methyl salt (E)-10. Mono- and di-N-methylated salts of conjugate (E,E)-5 and (Z,Z)-5, were obtained by quaternation with iodomethane. The (Z,Z)-5 di-N-methylated salt forms charge-transfer complexes with TCNE, TCNQ and TMPD. 相似文献
3.
Raju Ranjith Kumar 《Tetrahedron》2007,63(33):7850-7857
A series of new 2-methyl-11-aryl-4-[(E)-arylmethylidene]-1,2,3,4,11,11a-hexahydropyrido[3,4-c][1,5]benzothiazepines were obtained by the reaction of o-aminothiophenol and (E)-1-methyl-3,5-bis(arylidene)-4-piperidones in the presence of a catalytic amount of acetic acid under solvent-free microwave irradiation. These dipolarophiles undergo a highly atom economic 1,3-dipolar cycloaddition with nitrile oxide to afford a series of novel 6-methyl-1-phenyl-8-aryl-4-[(E)-arylmethylidene]-4,5,6,7,7a,8-hexahydro[1,2,4]oxadiazolo[5,4-d]pyrido[3,4-c][1,5]benzothiazepines stereoselectively. 相似文献
4.
O. A. Ignatenko M. A. Kuznetsov S. I. Selivanov 《Russian Journal of Organic Chemistry》2007,43(7):1042-1047
Oxidation of N-aminophthalimide with lead tetraacetate in the presence of 2-[(E)-2-arylethenyl]-5-phenyl-1,3,4-oxadiazoles gives the corresponding 2-(3-aryl-1-phthalimidoaziridin-2-yl)-5-phenyl-1,3,4-oxadiazoles. From 2-phenyl-5-[(1E,3E)-4-phenylbuta-1,3-dien-1-yl]-1,3,4-oxadiazole only the addition product at both C=C bonds was obtained, while in the reaction with 2,5-bis[(E)-2-phenylethenyl]-1,3,4-oxadiazole both mono- and bis-adducts were isolated. 相似文献
5.
Ni(acac)2 catalyzes the four-component connection reaction of diphenylzinc, isoprene, aromatic aldehydes, and aromatic amines in this order and provides stereochemically homogeneous (E)-1-arylamino-1-aryl-3-methyl-5-phenyl-3-pentenes (1) in excellent yields. Aliphatic aldehydes react similarly and give (E)-1-arylamino-1-alkyl-3-methyl-5-phenyl-3-pentenes (1) in slightly reduced yields. When the alkyl groups are bulky, in addition to 1 are formed (E)-1-arylamino-1-alkyl-4-methyl-5-phenyl-3-pentenes (1′) as the minor products. Lactamines prepared in situ from five- and six-membered lactols and aromatic amines are more reactive than alkyl aldehyde aldimines and furnish (E)-4-arylamino-6-methyl-8-phenyl-6-octen-1-ols (4) and (E)-5-arylamino-7-methyl-9- phenyl-7-nonen-1-ols (5), respectively, in good yields with excellent E-stereoselectivity. 相似文献
6.
Substituted 2,3,5,6,7,8-hexahydropyrazolo[4,3-d][1,2]diazepine-8-carboxylates were prepared in good to excellent yields from ethyl (2E)-3-(dimethylamino)-2-{(4Z)-4-[(dimethylamino)methylidene]-5-oxo-1-phenyl-4,5-dihydro-1H-pyrazol-3-yl}propenoate with 1,2-disubstituted hydrazines by heating in an alcohol. 相似文献
7.
V. S. Matiichuk M. A. Potopnyk N. D. Obushak 《Russian Journal of Organic Chemistry》2009,45(5):712-718
The reaction of ethyl 4-formyl-1-phenyl-1H-pyrazole-3-carboxylate with the malonic acid led to the formation (2E)-3-(3-ethoxycarbonyl-1-phenyl-1H-pyrazol-4-yl)propenic acid. In reactions of this acid chloride with 4-amino-5-aryl(hetaryl)-4H-1,2,4-triazole-3-thiols were obtained ethyl 4-[(E)-2-{3-aryl(hetaryl)[1,2,4]triazolo[3,4-b][1,3,4]thiadiazol-6-yl}ethenyl]-1-phenyl-1H-pyrazoe-3-carboxylates, with 5-aryltetrazoles, ethyl 4-[(E)-2-(5-aryl-1,3,4-oxadiazol-2-yl)-ethenyl]-1-phenyl-1H-pyrazole-3-carboxylates, with 1-(2-hydroxy-3,5-dimethylphenyl) followed by the Baker-Venkataraman rearrangement and the cyclization, ethyl 4-[(E)-2-(6,8-dimethyl-4-oxo-4Hchromen-2-yl)ethenyl]-1-phenyl-1H-pyrazole-3-carboxylate. 相似文献
8.
Jens HartungMarco Greb 《Tetrahedron letters》2003,44(32):6091-6093
The vanadium(V)-catalyzed oxidation of bromide in the presence of methyl (E)-2-(1-hydroxy-1-methylethyl)-5-phenyl-4-hexenoate furnished 5,6-trans-5-bromo-6-phenyl-2,2,6-trimethyl-3-methyloxycarbonyltetrahydropyran, which was converted into the marine natural product aplysiapyranoid A and its 5-epimer, via a short sequence of decarboxylative bromination and transition metal-based procedures for transforming a phenyl into a chlorovinyl substituent. 相似文献
9.
O. A. Ignatenko A. N. Blandov M. A. Kuznetsov 《Russian Journal of Organic Chemistry》2005,41(12):1793-1801
Oxidation of N-aminophthalimide with lead tetraacetate in the presence of 1,5-diaryl-3-[(E)-2-arylethenyl]-1H-pyrazoles, as well as of 1,3-diphenyl-5-[(E)-2-phenylethenyl]-1H-pyrazole, gives adducts at the exocyclic C=C bond, the corresponding phthalimidoaziridinylpyrazoles. From 1,5-diphenyl-3-[(1E,3E)-4-phenyl-1,3-butadienyl]-1H-pyrazole, only product of addition at both exocyclic C=C bonds was obtained. In the reaction with 1-phenyl-3-[(1E, 3E)-4-phenyl-1,3-butadienyl]-5-[(E)-2-phenylethenyl]-1H-pyrazole, the adduct at the styryl C=C bond was isolated. Analogous 4,5-dihydropyrazoles, 1,5-diphenyl-3-[(1E, 3E)-4-phenyl-1,3-butadienyl]-4,5-dihydro-1H-pyrazole and 1-phenyl-3-[(1E, 3E)-4-phenyl-1,3-butadienyl]-5-[(E)-2-phenylethenyl]-4,5-dihydro-1H-pyrazole, turned out to be inert in oxidative addition of N-aminophthalimide. 相似文献
10.
I. V. Dyachenko V. D. Dyachenko E. B. Rusanov 《Russian Journal of Organic Chemistry》2007,43(1):83-89
Knoevenagel condensation of N-hetaryl-substituted cyanoacetamides with aldehydes gave the corresponding (E)-N-hetaryl-2-cyanoacrylamides which were converted into (E)-N-alkyl-N-hetaryl-2-cyanoacrylamides and 6-amino-2-oxo-4-phenyl-1-(pyridin-2-yl)-1,2-dihydropyridine-3,5-dicarbonitriles. The structure
of (E)-N-(pyridin-2-yl)-2-cyano-3-phenylprop-2-enamide was determined by X-ray analysis.
Original Russian Text ? I.V. Dyachenko, V.D. Dyachenko, E.B. Rusanov, 2007, published in Zhurnal Organicheskoi Khimii, 2007,
Vol. 43, No. 1, pp. 81–86. 相似文献
11.
Synthesis of 2-(3,4,5-trimethoxybenzoyl)-4(5)-phenyl-1<Emphasis Type="Italic">H</Emphasis>-imidazole
E. B. Nikolaenkova I. A. Os’kina A. Ya. Tikhonov 《Russian Journal of Organic Chemistry》2017,53(12):1887-1889
The condensation of (2E)-N-hydroxy-2-hydroxyimino-2-phenylethanamine with 3,4,5-trimethoxyphenylglyoxal afforded (1-hydroxy-5-phenyl-1H-imidazol-2-yl)phenylmethanone which reacted with trimethyl phosphite or chloroacetone to give 2-(3,4,5-trimethoxybenzoyl)-4(5)-phenyl-1H-imidazole. 相似文献
12.
The total synthesis of methyl β-d-vicenisaminide 1 has been achieved. In this approach, the synthesis of enantiomerically pure methyl (4R,5S)- and (4S,5R)-4-azido-5-hydroxy-2(E)-hexenoates 2 was established by enzymatic resolution of (±)-anti-5-acetoxy -4-azido-2(E)-hexenoate 4. Another stereogenic center was introduced by base-catalyzed intramolecular conjugate addition of a hemiacetal-derived alkoxide nucleophile obtained by the reaction of methyl (4S,5R)-N-4-tert-butoxycarbonyl-N-methylamino-5-hydroxyl-2(E)-hexenoate 8 and benzaldehyde in the presence of a base. 相似文献
13.
We report herein the synthesis of a novel class of compounds, ethyl 4-oxo-4H-furo[3,2-c]pyran-6-yl carbonate, (7E)-7-[(dimethylamino)methylene]-4H-furo[3,2-c]pyran-4,6(7H)-dione, 5-oxo-N-phenyl-2,5-dihydro-4H-furo[3,2-b]pyrrole-4-carboxamide, and 5-oxo-N-phenyl-5,6-dihydro-4H-thieno[3,2-b]pyrrole-4-carboxamide starting from the corresponding acid derivatives. Intramolecular cyclization in the presence of thionyl chloride formed the target fused ring systems. Additional transformation was seen in the cyclization of furan-fused heterocycle. A mechanism was proposed based on experimental and computational findings. 相似文献
14.
Isoxazolines 2 from the cycloaddition of imidazoline 3-oxides 1 with DMAD rearrange in the presence of methoxide to give cis-3-methoxy-7-(methoxycarbonyl)-2,7a-diaryl-5-oxo-2,3,5,7a-tetrahydro-1H-pyrrolo[1,2-e]imidazol-6-olates 3 with 100% de. The acidic hydrolysis of 3 led to kinetically controlled formation of methyl 1-formyl-4-hydroxy-5-oxo-2-phenyl-2-((arylamino)methyl)-2,5-dihydro-1H-pyrrole-3-carboxylates 6a-e. The intramolecular transformylations of the latter to the corresponding (E)- and (Z)-methyl 4-hydroxy-2-((N-(aryl)formamido)methyl)-5-oxo-2-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylates 7a-e were shown to be substituent dependent (correlate with σ) and characterized by Hammett type equations. The effect of temperature was investigated and the ρ constants determined for the same reaction series at 50, 60 and 70 °C. The amide diastereomeric ratio [(E)-7]/[(Z)-7] is substituent dependent and can be described by the equation log[(E)]/[(Z)]x=−ρσI+log[(E)]/[(Z)]x=H. 相似文献
15.
Shin-ichi Takekuma Kazutaka Mizutani Masaru Nakamura Toshie Minematsu Hideko Takekuma 《Tetrahedron》2007,63(18):3882-3893
Reaction of azulene (1) with all-trans-retinal in diethyl ether in the presence of hexafluorophosphoric acid at −10 °C for 1 h in a dark room gives the corresponding monocarbenium-ion compound, (2E,4E,6E,8E)-1-azulenyl-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ylium hexafluorophosphate (3), in 74% isolated yield. The spectroscopic, chemical, and electrochemical properties of 3 compared with those of the previously-documented (2E,4E,6E,8E)-1-(3-guaiazulenyl)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ylium hexafluorophosphate (4) are reported. Along with the above delocalized monocarbenium-ion compounds 3 and 4, stabilized by the expanded π-electron systems possessing an azulenyl (or 3-guaiazulenyl) group, an efficient preparation as well as the spectroscopic, chemical, and electrochemical properties of (2E)-1-azulenyl-3-phenyl-2-propen-1-ylium and (2E)-1-(3-guaiazulenyl)-3-phenyl-2-propen-1-ylium hexafluorophosphates (5 and 6) (90 and 96% isolated yields), having a similar partial structure [i.e., the (2E)-1-azulenyl-2-propen-1-ylium-ion or (2E)-1-(3-guaiazulenyl)-2-propen-1-ylium-ion part] to those of 3 and 4, is documented. Moreover, the crystal structure of 6, whose carbenium-ion framework is planar, is shown. 相似文献
16.
Highly functionalized (E)-stilbenes 3a-m and 4-aryl-6-styryl-pyran-2-ylidineacetonitriles 4a-b have been prepared and delineated through the ring transformation of 6-aryl-3,4-disubstituted-2H-pyran-2-ones 1 with commercially available (E/Z)-4-phenyl-3-buten-2-one 2 without the use of any catalyst. 相似文献
17.
Jacek Skar?ewski Mariola Zielińska-B?ajetSzczepan Roszak Ilona Turowska-Tyrk 《Tetrahedron》2003,59(20):3621-3626
Optically active (3R,1RS)-3-aryl-1-phenyl-3-phenylsulfanyl-1-propanols were easily dehydrated forming mainly rac-cis-2-aryl-4-phenylthiochroman, and rac-cis-4-aryl-2-phenylthiochroman along with the corresponding trans-isomers. The observed reaction outcome (rearrangement and racemisation) apparently results from the SEAr reaction involving the unusual 1,3-phenylsulfanyl group migration. This interpretation is supported by the results of theoretical studies (DFT) on the supposed intermediates. 相似文献
18.
《Tetrahedron: Asymmetry》2001,12(18):2581-2587
From stereoisomeric α,β-unsaturated nitriles (E,Z)-1, the recombinant nitrilase AtNIT1 from Arabidopsis thaliana hydrolyses the (E)-isomers exclusively to the corresponding (E)-carboxylic acids (E)-2 with high specificity. The (E)-selectivity can also be utilised for the preparation of the isomerically pure nitriles (Z)-1. From (E,Z)-2-hydroxycinnamonitrile (E,Z)-3, the otherwise difficult obtainable (Z)-3 was prepared in 66% isolated yield. With β,γ-unsaturated (E,Z)-3-heptenenitrile (E,Z)-4, however, (E)-selectivity was not observed. AtNIT1 exhibits not only diastereoselectivity but also regioselectivity. From a mixture of the four isomers A–D of 3-(2-cyanocyclohex-3-enyl)propenenitrile 6, exclusively isomer D ((E)-cis-6) was hydrolysed to 3-(2-cyanocyclohex-3-enyl)propenoic acid (E)-cis-7, as stated by X-ray crystal structure. Only after complete conversion of D and high enzyme concentrations, isomer C ((E)-trans-6) was hydrolysed to a small extent. 相似文献
19.
《Tetrahedron: Asymmetry》2000,11(14):3017-3025
(1S,2S)-(+)-Thiomicamine was transformed in high yield and with high diastereoselectivity into (3R,4R)-4-phenyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid and enantiomerically pure (3R,4R)-3-hydroxymethyl-4-phenyl- and (1R,3R,4R)-3-hydroxymethyl-1-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline derivatives. 相似文献
20.
A. A. Golovanov I. S. Odin V. V. Bekin A. V. Vologzhanina I. S. Bushmarinov S. S. Zlotskii Yu. L. Gerasimov P. P. Purygin 《Russian Journal of Organic Chemistry》2016,52(3):414-420
Huisgen reaction of (E)-1,5-diarylpent-2-en-4-yn-1-ones and (E)-1,5-diarylpent-1-en-4-yn-3-ones afforded 1-aryl-3-(5-aryl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones and 3-aryl-1-(5-aryl-1H-1,2,3-triazol-4-yl)-prop-2-en-1-ones, respectively. (E)-1-Aryl-3-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones reacted with hydrazine hydrate and phenylhydrazine to give 72–93% of 4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles which underwent dehydrogenation on heating in boiling acetic acid with formation of the corresponding pyrazole derivatives. The molecular structures of (E)-3-phenyl-1-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one and 4-[3-(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl]-5-phenyl-1H-1,2,3-triazole were studied by X-ray analysis. 4-(3-Aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles showed toxicity against Daphnia magna. 相似文献