- Novel Aminomethyl Derivatives of 4-Methyl-2-prenylphenol: Synthesis and Antioxidant Properties
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4-Methyl-2-prenylphenol (1) was synthesized from para-cresol and prenol, natural alcohol under the conditions of heterogeneous catalysis. A series of nine new aminomethyl derivatives with secondary and tertiary amino groups were obtained on the basis of compound 1. A comparative evaluation of their antioxidant properties was carried out using in vitro models. It was established that Mannich base with octylaminomethyl group has radical-scavenging activity, high Fe2+-chelation ability as well as the ability to inhibit oxidative hemolysis of red blood cells.
- Buravlev, Evgeny V.,Fedorova, Irina V.,Shevchenko, Oksana G.,Kutchin, Aleksandr V.
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- Comparative evaluation of antioxidant activity of 2-alkyl-4-methylphenols and their 6-n-octylaminomethyl derivatives
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A series of 2-alkyl-4-methyl-6-n-octylaminomethylphenols (where alkyl is methyl or tert-butyl group, or terpene substituent) was synthesized. A comparative evaluation of the antioxidant properties of the starting alkyl- and terpenylphenols and their Mannich bases was carried out using in vitro assays. Structural features providing high antioxidant activity of these compounds were revealed.
- Buravlev,Fedorova,Shevchenko
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- Prenylation of 4-Methylphenol
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Abstract: Organoaluminum (aluminum phenolate and aluminum isopropylate) and acidicheterogeneous catalysts (zeolites C-10, C-100 and ZSM, clay KSF, sulfonic cationexchangers Fiban K-1 and Amberlist 36 Dry) were studied in the alkylation of4-methylphenol wi
- Chukicheva, I. Yu.,Fedorova, I. V.,Kolegova, Т.А.,Kutchin, A. V.
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p. 335 - 340
(2020/04/27)
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- Synthesis of n-arylpyrazoles by palladium-catalyzed coupling of aryl triflates with pyrazole derivatives
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A method for the synthesis of N-arylpyrazoles by palladium-catalyzed coupling of aryl triflates with pyrazole derivatives is described. Using tBuBrettPhos as a ligand, the palladium-catalyzed C-N coupling of a variety of aryl triflates including ortho-substituted ones with pyrazole derivatives proceeded efficiently to give N-arylpyrazole products in high yields. 3-Trimethylsilylpyrazole was found to be an excellent pyrazole substrate for the coupling, and the corresponding product, 1-aryl-3-trimethylsilylpyrazole, also served as a great template for the syntheses of N-arylpyrazole derivatives, as demonstrated by regioselective halogenation at the 3-, 4-, and 5-positions of the pyrazole ring.
- Onodera, Shunsuke,Kochi, Takuya,Kakiuchi, Fumitoshi
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- Synthesis of N-Arylpyrazoles by Palladium-Catalyzed Coupling of Aryl Triflates with Pyrazole Derivatives
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A method for the synthesis of N-arylpyrazoles by palladium-catalyzed coupling of aryl triflates with pyrazole derivatives is described. Using tBuBrettPhos as a ligand, the palladium-catalyzed C-N coupling of a variety of aryl triflates including ortho-substituted ones with pyrazole derivatives proceeded efficiently to give N-arylpyrazole products in high yields. 3-Trimethylsilylpyrazole was found to be an excellent pyrazole substrate for the coupling, and the corresponding product, 1-aryl-3-trimethylsilylpyrazole, also served as a great template for the syntheses of N-arylpyrazole derivatives, as demonstrated by regioselective halogenation at the 3-, 4-, and 5-positions of the pyrazole ring.
- Onodera, Shunsuke,Kochi, Takuya,Kakiuchi, Fumitoshi
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p. 6508 - 6515
(2019/05/24)
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- A surprising substituent effect provides a superior boronic acid catalyst for mild and metal-free direct Friedel-Crafts alkylations and prenylations of neutral arenes
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The development of more general and efficient catalytic processes for Friedel-Crafts alkylations is an important objective of interest toward the production of pharmaceuticals and commodity chemicals. Herein, 2,3,4,5-tetrafluorophenylboronic acid was identified as a potent air- and moisture-tolerant metal-free catalyst that significantly improves the scope of direct Friedel-Crafts alkylations of a variety of slightly activated and neutral arenes, including polyarenes, with allylic and benzylic alcohols. This method also provides a simple alternative for the direct installation of prenyl units commonly found in naturally occurring arenes. Alkylations with benzylic alcohols occur under exceptionally mild conditions.
- Ricardo, Carolynne L.,Mo, Xiaobin,McCubbin, J. Adam,Hall, Dennis G.
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supporting information
p. 4218 - 4223
(2015/03/14)
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- Highly Selective Synthesis of Ortho-Prenylated Phenols and Chromans by using a New Bimetallic CuAl-KIT-5 with a 3D-Cage-type Mesoporous Structure
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A nice piece of KIT: The first synthesis of a new bimetallic 3D-cage-type mesoporous catalyst CuAl-KIT-5 and its remarkable performance for the highly selective synthesis of ortho-prenylated phenols and chromans is reported.
- Varghese, Shaji,Anand, Chokkalingam,Dhawale, Dattatray,Mane, Gurudas P.,Wahab, Mohammad A.,Mano, Ajayan,Raj, George Allen Gnana,Nagarajan, Samuthira,Vinu, Ajayan
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p. 899 - 902
(2013/05/08)
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- Bismuth(III) triflate: Novel and efficient catalyst for Claisen and Fries rearrangements of allyl ethers and phenyl esters
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Bismuth(III) triflate catalyzed Claisen and Fries rearrangements of allyl phenyl ethers and phenyl acetates have been presented. The reaction proceeds smoothly and yields corresponding rearranged products in good yields. The bismuth triflate displays higher activity over the corresponding La, Yb, and Sc triflates.
- Sreedhar,Swapna,Sridhar
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p. 1433 - 1440
(2007/10/03)
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- Regioselectivity in the ene reaction of singlet oxygen with ortho-prenylphenol derivatives
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The ene reaction of singlet oxygen with prenylated dihydroxyacetophenones led to the 2-hydroperoxy-3-methylbut-3-enyl derivatives as the major product. This original regioselectivity outlined a new effect, in competition with the previously established la
- Helesbeux, Jean-Jacques,Duval, Olivier,Guilet, David,Séraphin, Denis,Rondeau, David,Richomme, Pascal
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p. 5091 - 5104
(2007/10/03)
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- Organic Synthesis with sulfones. XLI. Nucleophilic substitution of allylic sulfones
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The sulfonyl group in allylic sulfones can be displaced by a variety of nucleophiles.The reaction is particularly easy with tertiary sulfones, i.e. bearing no hydrogen atoms at the α-position.Lewis acids catalyse the displacement reaction.
- Julia, Marc,Nel, Maurice,Uguen, Daniel
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p. 487 - 492
(2007/10/02)
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- REGIOSPECIFIC ALKENYLATION OF PHENOLS BY ISOPRENE PROMOTED BY Pt(II) AND Pd(II) COMPLEXES
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Catalytic alkenylation of phenols with isoprene is promoted by Pd(II) or Pt(II) complexes.Ortho-isopentenylphenols are obtained together with the corresponding 2,2-dimethylchromans.The catalytic activity of the two d8 ions is compared.A possible mechanism is discussed.
- Felice, Vincenzo De,Renzi, Augusto De,Funicello, Maria,Panunzi, Achille,Saporito, Antonio
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- REGIOSPECIFIC ALKENYLATION OF PHENOLS BY 1,1-DIMETHYLALLENE PROMOTED BY PLATINUM CATALYSTS
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1,1-Dimethylallene reacts with phenolic substrates in the presence of catalytic amounts of platinum(II) complexes.A regiospecific C-alkenylation takes place, affording o-isopentenylphenols and 2,2-dimethylchromans.Possible reaction mechanisms are also discussed.
- Renzi, Augusto De,Panunzi, Achille,Saporito, Antonio,Vitagliano, Aldo
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p. 993 - 996
(2007/10/02)
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- THERMAL AND CATALYTIC REARRANGEMENTS OF 4-(1,1-DIMETHYL-2-PROPENOXY)TOLUENE
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During the thermal and catalytic rearrangements of 4-(1,1-dimethyl-2-propenoxy)toluene the Claisen phenol, with inversion of the allyl unit, i.e., 4-methyl-2-(3-methyl-2-butenyl)phenol, is formed primarily.The formation of 2-methyl-2-(3-methyl-2-butenyl)phenol in the catalytic rearrangement with the introduction of o-cresol into the reaction zone shows that this rearrangement has partly intermolecular character.Consequently, the Claisen phenol can also be obtained by an intermolecular path, where this phenol is the most thermodynamically stable isomer.
- Aleksandrova, E. K.,Bunina-Krivorukova, L. I.
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p. 742 - 745
(2007/10/02)
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- EFFECT OF STRONG NUCLEOPHILE ON THE DIRECTION OF TRANSFORMATION IN ALKENYL ARYL ETHERS DURING CATALYTIC REARRANGEMENT
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The results from the introduction of tetrahydrothiophene into the reaction zone during the catalytic rearrangements of alkenyl aryl ethers demonstrate the possibility of a change in the direction of transformation of the ether from -sigmatropic rearrangement to intermolecular alkenylation of a concurrent strong nucleophile.The heterolytic character of the catalytic intermolecular rearrangement (alkenylation) was confirmed by the formation of alkenylsulfonium salts, the structure of the allyl unit which corresponded to the most thermodynamically stable isomer.
- Bunina-Krivorukova, L. I.,Feoktistov, V. M.,Aleksandrova, E. K.,Bal'yan, Kh. V.
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p. 745 - 750
(2007/10/02)
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