- One-pot synthesis of cage alcohols
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An efficient one-pot procedure has been developed for the synthesis of cage alcohols with hydroxy groups in the bridgehead positions. The procedure includes initial nitroxylation with nitric acid or a mixture of nitric acid with acetic acid and subsequent hydrolysis in the presence of urea.
- Klimochkin, Yu. N.,Yudashkin,Zhilkina,Ivleva,Moiseev,Oshis, Ya. F.
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p. 971 - 976
(2017/09/07)
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- Synthesis and biological evaluation of memantine nitrates as a potential treatment for neurodegenerative diseases
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A series of memantine nitrate derivatives, as dual functional compounds with neuroprotective and vasodilatory activity for neurodegenerative diseases, was designed and synthesized. These compounds combined the memantine skeleton and a nitrate moiety, and thus inhibited the N-methyl-d-aspartic acid receptor and released NO in the central nervous system. The biological evaluation results revealed that the new memantine nitrates were effective in protecting neurons against glutamate-induced injury in vitro. Moreover, memantine nitrates dilated aortic rings against phenylephrine-induced contraction. The structure-activity relationships of neuroprotection and vasodilation were both analyzed. In further studies, compound MN-05 significantly protected cortical neurons by inhibiting Ca2+ influx, reducing free radical production and maintaining the mitochondrial membrane potential. Further research on MN-05 is warranted.
- Liu, Zheng,Yang, Si,Jin, Xiaoyong,Zhang, Gaoxiao,Guo, Baojian,Chen, Haiyun,Yu, Pei,Sun, Yewei,Zhang, Zaijun,Wang, Yuqiang
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p. 135 - 147
(2017/02/05)
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- Synthesis of hydroxy derivatives from adamantanecarboxylic acids in the system MnO2–H2SO4
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A convenient procedure has been developed for the synthesis of mono- and dihydric cage alcohols from adamantanecarboxylic acids and their esters using the MnO2–H2SO4system. The reaction at elevated temperature involved both decarboxylation and decarbonylation of the initial acid or ester.
- Ivleva,Gavrilova,Klimochkin, Yu. N.
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p. 785 - 790
(2016/07/30)
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- Efficient oxidation of adamantanes by sodium nitrite with molecular oxygen in trifluoroacetic acid
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Oxidation of adamantanes by oxygen was effectively achieved by use of sodium nitrite as a catalyst in trifluoroacetic acid (TFA) to give 1-adamantyl trifluoroacetates, from which adamantanols were obtained in good yields. A catalytic amount of sodium nitrite was essential and TFA was the best solvent among solvents examined for this oxidation. Georg Thieme Verlag Stuttgart.
- Onomura, Osamu,Yamamoto, Yutaka,Moriyama, Noriaki,Iwasaki, Fumiaki,Matsumura, Yoshihiro
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p. 2415 - 2418
(2008/02/10)
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- Formation of adamantan-1-ols by the reactions of adamantanes with 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) in trifluoromethanesulfonic acid
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Adamantanes were treated with DDQ in trifluoromethanesulfonic acid followed by hydrolysis to give adamantan-1-ols in good yields.
- Tanemura,Suzuki,Nishida,Satsumabayashi,Horaguchi
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p. 3230 - 3231
(2007/10/03)
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- Phosphorylation of Adamantane and its Derivatives in Trifluoroacetic Acid Medium
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The possibility of dichlorophosphorylation of the carcass compounds of the adamantane series and of aryl(alkyl)carbinols, with phosphorus trichloride in the low-nucleophilicity trifluoroacetic acid medium was first demonstrated. A new preparative method for introducing a POCl2 group into the bridgehead and bridge positions of the adamantane nucleus, as well as into the α position of the side chain was developed. Some intermediate adamantyl cations may undergo isometizations, among them skeleton ones. A mechanism of the phosphorylation was proposed.
- Shokova,Erokhin,Kovalev
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p. 1624 - 1634
(2007/10/03)
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- REACTION OF ALCOHOLS WITH BROMINE
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Framework hydrocarbons react with bromine in water to form tertiary alcohols.In the absence of moisture the various alcohols react with bromine by a nucleophilic substitution mechanism, forming alkyl bromides.
- Baklan, V. F.,Khil'chevskii, A. N.,D'yakovskaya, V. M.,Sologub, L. S.,Kukhar, V. P.
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p. 454 - 456
(2007/10/02)
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- TRANSANNULAR IONIC HYDROGENATION, AND ACIDIC CYCLIZATION AND ISOMERIZATION REACTIONS OF 3,7-DIMETHYLENEBICYCLONONANE AND ITS DERIVATIVES
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The ionic hydrogenation, isomerization, and cyclization reactions of 3,7-dimethylenebicyclononane and related compounds have been studied.Ionic hydrogenation of the exocyclic methylene ?-bond occurs via the formation of alkyladamantanes.Reaction of 3,7-dimethylenebicyclononane with a chiral reagent results in the formation of an asymmetric adamantane derivative with an enantiomeric purity similar to that of the starting diene.
- Krasutskii, P. A.,Ambrosienko, N. V.,Rodionov, V. N.,Yurchenko, A. G.,Parnes, Z. N.,Bolestova, G. I.
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p. 1333 - 1337
(2007/10/02)
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- Synthese en serie adamantane : preparation d'adamantanes trisubstitues-1,2,3 et -1,2,5 et de protoadamantanones -4 substituees en position -6 ou -8
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A regio and diastereospecific synthetic approach to 1,3-dialkyl (and 1,3-diphenyl) adamantanes bearing a functional group in position-2 (7) and to 1,5-dialkyl (and 1,5-diphenyl) 2-adamantanols (syn 8) is described.This has been accomplished through an addition-isomerisation process on two new classes of 4-protoadamantanones bearing a substituent in position 8 or 6 (3 and 4).These have been prepared via an intramolecular base catalysed cyclisation of iodoketones (11), obtained by thermolysis of hypo-iodites (10).
- Drivas, Ioannis,Mison, Pierre
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p. 252 - 264
(2007/10/02)
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- Polar Effects. X. Polar Substituent Effects in the Solvolysis of 3-Substituted 1-Adamantyl Bromides and Tiluenesulfonates
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The rate constants for 3-substituted adamantyl p-toluenesulfonated 3a-3k in ethanol/water 80:20 correlate well with the respective inductive subsitutent constants ?qI.The reaction constant ρ for the toluenesulfonates 3 is 10percent karger than for the corresponding bromides 2, indicating somewhat more charge separation in the activation of the toluenesulfonates.Evidence is presented that stabilization of the resultant 1-adamantyl cations by induction involves graded 1,3-bridging, which is favored when the subsituent is an electrofugal group, and that stabilization by n-electron donors involves C,C-hyperconjugation.Rate ratios for the toluenesulfonates 3 and the bromides 1 exceed 1E3 and are almost independent of the 3-subsituents.The implications of this are discussed in the light current hypotheses.
- Grob, Cyril A.,Schaub, Bruno
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p. 1720 - 1727
(2007/10/02)
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- Reaction of Diphenyl- and Difluorocarbenes with 3,7-Dimethylenebicyclononane
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Both difluorocarbene and diphenylcarbene add to 3,7-dimethylenebicyclononane to give mono- and diadducts.Products of abstraction-recombination are produced from diphenylcarbene, but neither carbene gives products of conjugate addition.
- Krasutsky, Pavel A.,Jones, Maitland
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p. 2425 - 2429
(2007/10/02)
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