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Halogenation of 6(5H)-phenanthridinone or its 3,8-dihalo derivatives with N-bromo or N-chlorosuccinimide in dimethylformamide gives the corresponding 2-halophenanthridinones (I,V,XI-XIV). Further halogenation of 2-halo-6(5H)-phenanthridinone with the appropriate N-halosuccinimide, in the same medium, gives the corresponding 2,4-dihalo derivatives (II,VI). NXS/DMF is found to be a very convenient halogenating system in these preparations. 1,3,8-Trihalo-6(5H)-phenanthridinones (XIX,XX) are prepared from the 1-nitro derivatives which are obtained by a Schmidt rearrangement of 2,7-dihalo-4-nitro-9-oxofluorenes. Similarly, rearrangement and further reaction of 2-nitro-5-chloro-9-oxofluorene (XXI) leads to 3,10-dichloro-6(5H)-phenanthridinone (XXIV). UV absorptions as well as selected IR absorptions of these 6(5H)-phenanthridinones are described. 相似文献
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Aromatization of the title compound with selected acidic catalysts has been investigated. It has been established that depending upon the reaction conditions trienone 2,1 -methyltrienone3, dienone 4, diacetoxyketone5 or dione 6 are formed as the major products. Dienone 4 and dione 6 are the main compounds of the reactions of tosyloxyketone 10 with KHSO4 and HBraq, respectively. The reaction of acetoxyketone 8 with HBraq furnishes epimeric 3-bromoketones 12 and 13 in the ratio about 1:1. 相似文献
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A. M. Andrievskii O. V. Chelysheva A. N. Poplavskii V. V. Nikonov L. A. Chetkina V. K. Bel'skii V. E. Zavodnik A. A. Perov N. A. Andronova K. M. Dyumaev 《Chemistry of Heterocyclic Compounds》1990,26(6):658-663
Treatment of 2-bromo-6(5H)-phenanthridone with nitrating mixture or fuming nitric acid results in nitration, debromination, and bromination in the 10-position. The brominating agent is apparently Br+, formed in the reaction mixture following replacement of the bromine in the 2-position by a nitro-group. Monocrystals of 2-bromo-1,4,8-trinitro-6(5H)-phenanthridinone and 10-bromo-2,4,8-trinitro-6(5H)-phenanthridinone have been subjected to x-ray diffraction examination. PMR has been used for structural identification.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 789–795, June, 1990.We thank A. N. Sobolev for assistance in calculating the structure of (III). 相似文献
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A. M. Andrievskii A. N. Poplavskii K. M. Dyumaev Yu. S. Bogachev S. S. Berestova 《Chemistry of Heterocyclic Compounds》1985,21(8):924-931
Methods for the preparation of nitro-substituted 6(5h)-phenanthridinones were examined. The nitration of 6(5H)-phenanthridinone, 5-methyl-6-(5H)- phenanthridinone, and 2-bromo-6(5H)-phenanthridinone was studied, and 2-, 3-, 4-nitro-, 2,4-, 2,8-, 4,8-dinitro-, 2,4,8-trinitro-, and 2,4,8,10-tetranitro-6(5H)-phenanthridinones, 2,4,8-trinitro- and 2,4,8,10-tetranitro-6-(5H)-phenanthridinones, and 2-bromo-4,8-dinitro- and 2-bromo-4,8,10-trinitro-6-(5H)-phenanthridinones were obtained. Proton magnetic resonance spectroscopy was used to identify the structure and predict the orientation of substitution in the nitration of 6(5H)-phenanthridinone and its nitro-substituted derivatives. The distribution of the electron density in these compounds was evaluated from an analysis of the chemical shifts of the protons.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1106–1113, August, 1985. 相似文献
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Gowravaram Sabitha Gajangi Chandrashekhar Kurra Yadagiri Jhillu Singh Yadav 《Tetrahedron: Asymmetry》2011,22(18-19):1729-1735
The total syntheses of the first examples of diarylheptanoid natural products (5S)-5-acetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)-3-heptanone 1, and (3S,5S)-3,5-diacetoxy-1,7-bis(4-hydroxy-3-methoxyphenyl)heptane 2 isolated from the rhizomes of Zingiber officinale were accomplished using Sharpless epoxidation and cross-metathesis reactions as the key steps. 相似文献
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The base catalyzed reaction of 2-aminoethanethiol ( 3 ) with trans-3-(p-methoxyphenyl)glycidate ( 4 ) gave a mixture of isomeric lactams 5 and 6 , and in addition, a by-product 7 . The structures of these isomers were proven by X-ray crystallography. The data revealed that both isomers adopt the chair conformation in the solid state and the size of the heterocyclic ring in compound 5 is a six- and in compound 6 is a seven-membered ring. 相似文献
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Bernard Chantegrel Christian Deshayes Bernard Pujol Zhong Jia Wei 《Journal of heterocyclic chemistry》1990,27(4):927-934
The title compounds were prepared from ethyl 5-acyl- or 5-(1-hydroxyethenyl)isoxazole-4-carboxylates which in turn were prepared from ethyl 3-methylamino-2-butenoate or 3(2H)-furanones. 相似文献
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Addition of chlorine to methyl 3-(dichloromethyl)-4,4-dichlorocrotonate (1), a critical procedure in the total synthesis of the title compound MX, was modified by using novel catalysts. A minor modification in the purification of MX was also described. 相似文献
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Conclusions We have prepared oxirane (IV) by reaction of pregnenolone acetate (II) with fimdyldofium in yields of up to 90%; treatment with BF3 etherate quantitatively isomerized it to (20R)-3-acetoxy-5-bisnorcholenal (III).Translated from Izvestiya Akademii, Nauk SSSR, Seriya Khimicheskaya, No. 11, pp. 2581–2584, November, 1976. 相似文献
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A new high-yield two step synthesis of 7,8-dihydroisoquinolin-5(6H)-one (3) from 5,6,7,8-tetrahydroisoquinoline (1) is described. 相似文献
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The title compound 5 has been prepared from the previously obtained ketone 2 by acetylation of its enolate anion. Spectral properties, reactivity and the results of a crystal structure determination show that 5 is a nonplanar molecule without aromatic character. 相似文献
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The title compound 5-cyclopropyl-10-(4-fluorophenyl)-7,7-dimethyl-7,8-dihydro- 5H-indeno[1,2-b]quinolne-9,11(6H,10H)-dione was obtained by the reaction of 4-fluorobenzal- dehyde, 2H-indene-1,3-dione and 3-(cyclopropylamino)-5,5-dimethylcyclohex-2-enone in the presence of acetic acid under microwave irradiation. Its structure was confirmed by IR and 1H- NMR spectra. The crystal is of monoclinic, space group P21/c with a = 14.138(3), b = 8.952(2), c = 17.140(3) , β = 102.253(3)o, C27H24FNO2, Mr = 413.47, Z = 4, V = 2119.9(8) 3, Dc = 1.296 g/cm3, μ(MoKα) = 0.087 mm-1, F(000) = 872, the final R = 0.0425 and wR = 0.0905 for 2336 observed reflections (I > 2σ(I)). X-ray analysis revealed that the pyridine ring adopts a boat conformation and the six-membered ring fused with it assumes a twist boat conformation. 相似文献