共查询到10条相似文献,搜索用时 109 毫秒
1.
Myron M. Johnson Kennedy J. Ngwira Amanda L. Rousseau Andreas Lemmerer Charles B. de Koning 《Tetrahedron》2018,74(1):12-18
The synthesis of the benz[a]anthracene skeleton of the angucyclines is described. Key steps involve the Suzuki-Miyaura reaction, isomerization of an aromatic allyl substituent to the corresponding styrene, and the use of the ring closing metathesis reaction to construct a benzene ring. For example, exposure of 3-allyl-2-bromo-1,4,5-trimethoxynaphthalene to (2-formyl-4-methoxyphenyl)boronic acid under palladium catalysis conditions resulted in the formation of 2-(3-allyl-1,4,5-trimethoxynaphthalen-2-yl)-5-methoxybenzaldehyde. This 2-naphthyl benzaldehyde then underwent a Wittig reaction to furnish 3-allyl-1,4,5-trimethoxy-2-(4-methoxy-2-vinylphenyl)naphthalene. Isomerization of the allyl group of this compound afforded the diene, (E)-1,4,5-trimethoxy-2-(4-methoxy-2-vinylphenyl)-3-(prop-1-en-1yl)naphthalene. Exposure of the formed diene to the Grubbs II catalyst resulted in the formation of the benzanthracene, 3,7,8,12-tetramethoxytetraphene, which was easily oxidized to the corresponding quinone. 相似文献
2.
《Tetrahedron》2014,70(32):4738-4744
Gram-scale total synthesis of (±)-8-[1-(4′-hydroxy-3′-methoxyphenyl)prop-2-en-1-yl]-galangin (1) and -chrysin (2) has been accomplished in eight steps from commercially available phloroglucinol and three steps from commercially available chrysin, respectively, featuring an efficient introduction of C(8) (1-prop-2-en-1-yl)phenyl moiety in the natural products through chemo- and regioselective cinnamylation and regioselective aromatic Claisen rearrangement. 相似文献
3.
Madhukar N. Jachak Sandeep M. Bagul Bhausaheb K. Ghotekar Raghunath B. Toche 《Monatshefte für Chemie / Chemical Monthly》2009,20(5):655-662
Abstract
A series of (2E)-3-(1-chloro-6-methoxy-3,4-dihydronaphthalen-2-yl)-1-(4-aryl)prop-2-en-1-ones (chalcones) have been synthesized by a new synthetic route. The 3-pyridinecarbonitrile derivatives were synthesized by the Michael reaction of malononitrile (in base) and aroylacetonitriles (in acid) with chalcones in one pot. The fluorescent properties and quantum yields of these compounds were studied. 相似文献4.
Citral extracted from Cymbopogon citratus (Gramineae) was subjected to photochemical epoxidation with hydrogen peroxide to obtain a mixture of epoxy derivatives at the C2=C3 and C6=C7 double bonds. The thermal oxidation of citral with m-chloroperoxybenzoic acid at room temperature gave only the corresponding 6,7-epoxy derivative as a mixture of E and Z isomers with respect to the C2=C3 double bond. Photosensitized oxygenation of citral in the presence of tetraphenylporphyrin, Rose Bengal, or chlorophyll lead
to a mixture of two isomeric hydroperoxides, (2E)-6-hydroperoxy-3,7-dimethylocta-2,7-dienal and (2E,5E)-7-hydroperoxy-3,7-dimethylocta-2,5-dienal. Epoxidation of pulegone isolated from Penny royal oil (Mentha pulegium, Lamiaceae) with hydrogen peroxide under irradiation with a sodium lamp lead to a mixture of cis- and trans-isomeric 2,2,6-trimethyl-1-oxaspiro[2.5]octan-4-ones, whereas under conditions of photosensitized oxygenation two hydroperoxide
derivatives, 2-(1-hydroperoxy-1-methylethyl)-5-methylcyclohex-2-en-1-one and 2-hydroperoxy-5-methyl-2-(1-methylethenyl)cyclohexan-1-one,
were also formed. Camphene reacted with hydrogen peroxide under irradiation to give a mixture of the corresponding endo- and exo-epoxy derivatives and camphor, while its thermal oxidation with m-chloroperoxybenzoic produced only the two former.
Published in Russian in Zhurnal Organicheskoi Khimii, 2008, Vol. 44, No. 6, pp. 825–833.
The text was submitted by the authors in English. 相似文献
5.
F. A. Gimalova G. M. Khalikova S. A. Torosyan D. Z. Akhmetshina M. S. Miftakhov 《Russian Journal of Organic Chemistry》2012,48(2):180-183
The oxidation with SeO2 of a methyl group linked to an sp2-hybridized carbon in the product of the intramolecular iodoetherification of cis-carveol afforded (1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]-oct-3-en-4-carbaldehyde and [(1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]oct-3-en-4-yl]methanol that were oxidized to methyl (1R,5R,7S)-7-iodomethyl-7-methyl-6-oxabicyclo[3.2.1]oct-3-en-4-carboxylate. The latter by the Zn-promoted opening of the γ-oxide ring
was converted into the target chiral block, methyl (4R,6R)-6-hydroxy-4-(prop-1-en-2-yl)cyclohex-1-encarboxylate. 相似文献
6.
Yu. N. Bubnov E. E. Demina V. K. Bel'sky G. V. Zatonsky A. V. Ignatenko 《Russian Chemical Bulletin》1998,47(11):2249-2255
Reductive tetraallylation of pyridine-3-and pyridine-4-carboxylic acids with triallylborane in the presence of propan-2-ol
proceeded stereoselectively to yieldtrans-2,6-diallyl-3- andtrans-2,6-diallyl-4-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,5,6-tetrahydropyridines, respectively. Under the same conditions, the
reaction with pyridine-2-carboxylic acid gave a mixture oftrans- andcis-2,6-diallyl-2-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,5,6-tetrahydropyridines in a ratio of 57:43. When 2,6-diphenylpyridine-4-carboxylic
acid reacted with triallylborane, only the carboxylic group underwent reductive diallylation. When heated with triallylborane
ino-xylene (130–133°C, 7 h),trans-2,6-diallyl-4-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,3,6-tetrahydropyridine was converted to the correspondingcis-isomer. The stereochemistry oftrans-2,6-diallyl-3-(1-allyl-1-hydroxybut-3-en-1-yl)-1,2,5,6,-tetrahydropyridine was confirmed by X-ray diffraction analysis.
Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 11, pp. 2320–2326, November, 1998. 相似文献
7.
<正>The synthesis of a new series of 3-(5-substituted benzimidazol-2-yl)-5-arylisoxazolines(6a-h) was achieved in excellent yields by the condensation of 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones(5a-h) with hydroxylamine at room temperature.These 1-(1H-benzimidazol-2-yl)-3-(substituted phenyl)prop-2-en-1-ones(5a-h) were obtained by the condensation of 2-acetyl benzimidazoles(4a-d) with different aromatic aldehydes,which in turn were obtained by the oxidation of 2-(α-hydroxy) ethyl benzimidazoles(3a-d) prepared by the reaction of o-phenylenediamines(1a-d) withα-hydroxy propionic acid 2. The synthesized compounds were characterized by their IR,~1H NMR and MS analyses.These compounds were screened for their antibacterial and antifungal activity by standard methods and found some of them active. 相似文献
8.
A. A. Panasenko A. F. Kaprosh M. A. Rekhter E. P. Styngach M. Z. Krimer G. N. Grushetskaya 《Russian Chemical Bulletin》1994,43(3):391-394
13C NMR spectra (20 and 75 MHz, in DMSO-d6) of a series of 1,3-diaryl-3-(1H-1,2,4-triazol-1-yl)- and 1,3-diaryl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-ones were registered. It was shown that the chemical shifts of both the carbon atom of the alkene group and C(3) reflect regio- and stereoisomerism of these compounds. Taking this into account the isomeric structures of several 1,3-diaryl-3-(1H-1,2,4-triazol-1-yl)prop-2-en-1-ones were identified and the configurations relative to the double bond of a number of 1,3-diaryl-2-(1H-1,2,4-triazol-1-yl)prop-2-en-1-ones were determined. 相似文献
9.
Madhukar N. Jachak Sandeep M. Bagul Bhausaheb K. Ghotekar Raghunath B. Toche 《Monatshefte für Chemie / Chemical Monthly》2009,140(6):655-662
Abstract A series of (2E)-3-(1-chloro-6-methoxy-3,4-dihydronaphthalen-2-yl)-1-(4-aryl)prop-2-en-1-ones (chalcones) have been synthesized by a new
synthetic route. The 3-pyridinecarbonitrile derivatives were synthesized by the Michael reaction of malononitrile (in base)
and aroylacetonitriles (in acid) with chalcones in one pot. The fluorescent properties and quantum yields of these compounds
were studied.
Graphical Abstract
相似文献
10.
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