- Photochemical Methoxide Exchange in Some Nitromethoxybenzenes. The Role of the Nitro Group in SN2Ar* Reactions
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Photoinduced methoxide exchange has been measured for o-, m-, and p-nitromethoxybenzene as well as for the methoxy-labeled 4-nitroveratroles.In these reactions (of the SN23Ar* type), where the substituting and leaving groups are the same, the origin of the meta activation found cannot be otherwise than in the steps leading to the symmetrical ? complex.Next to considerations on the basis of charge distributions of the excited aromatic compounds and of electron densities in the HOMO and LUMO, a rationalization for the regioselectivity and activation is offered on the basis of the energy gap between the ground-state and the excited-state surfaces.Since the level of the ground-state ? complex corresponding to meta substitution as compared to that for ortho/para substitution is highest in energy and since the trajectory from the (triplet) excited state leading to the ? complex for meta substitution is lowest in energy, the energy gap between the excited-state and ground-state hypersurface is considerable smaller for the geometry that leads to the meta ? complex and thus to meta substitution.Meta direction and activation of photosubstitutions will therefore be outspoken in the case of a substituent that gives difficult or no substitution at the meta position in the ground state and brings with it low triplet energy.The NO2 group conforms nicely to these criteria.
- Riel, H. C. H. A. van,Lodder, G.,Havinga, E.
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Read Online
- Synthesis and Antileishmanial Evaluation of Arylimidamide-Azole Hybrids Containing a Phenoxyalkyl Linker
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Due to the limitations of existing medications, there is a critical need for new drugs to treat visceral leishmaniasis. Since arylimidamides and antifungal azoles both show oral activity in murine visceral leishmaniasis models, a molecular hybridization approach was employed where arylimidamide and azole groups were separated by phenoxyalkyl linkers in an attempt to capitalize on the favorable antileishmanial properties of both series. Among the target compounds synthesized, a greater antileishmanial potency against intracellular Leishmania donovani was observed as the linker length increased from two to eight carbons and when an imidazole ring was employed as the terminal group compared to a 1,2,4-triazole group. Compound 24c (N-(4-((8-(1H-imidazol-1-yl)octyl)oxy)-2-isopropoxyphenyl) picolinimidamide) displayed activity against L. donovani intracellular amastigotes with an IC50 value of 0.53 μM. When tested in a murine visceral leishmaniasis model, compound 24c at a dose of 75 mg/kg/day p.o. for five consecutive days resulted in a modest 33% decrease in liver parasitemia compared to the control group, indicating that further optimization of these molecules is needed. While potent hybrid compounds bearing an imidazole terminal group were also strong inhibitors of recombinant CYP51 from L. donovani, as assessed by a fluorescence-based assay, additional targets are likely to play an important role in the antileishmanial action of these compounds.
- Abdelhameed, Ahmed,Feng, Mei,Joice, April C.,Zywot, Emilia M.,Jin, Yiru,La Rosa, Chris,Liao, Xiaoping,Meeds, Heidi L.,Kim, Yena,Li, Junan,McElroy, Craig A.,Wang, Michael Zhuo,Werbovetz, Karl A.
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p. 1901 - 1922
(2021/02/22)
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- Engineering Orthogonal Methyltransferases to Create Alternative Bioalkylation Pathways
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S-adenosyl-l-methionine (SAM)-dependent methyltransferases (MTs) catalyse the methylation of a vast array of small metabolites and biomacromolecules. Recently, rare carboxymethylation pathways have been discovered, including carboxymethyltransferase enzymes that utilise a carboxy-SAM (cxSAM) cofactor generated from SAM by a cxSAM synthase (CmoA). We show how MT enzymes can utilise cxSAM to catalyse carboxymethylation of tetrahydroisoquinoline (THIQ) and catechol substrates. Site-directed mutagenesis was used to create orthogonal MTs possessing improved catalytic activity and selectivity for cxSAM, with subsequent coupling to CmoA resulting in more efficient and selective carboxymethylation. An enzymatic approach was also developed to generate a previously undescribed co-factor, carboxy-S-adenosyl-l-ethionine (cxSAE), thereby enabling the stereoselective transfer of a chiral 1-carboxyethyl group to the substrate.
- Bennett, Matthew R.,Cronin, Victoria A.,Herbert, Abigail J.,Micklefield, Jason,Shepherd, Sarah A.,Sung, Rehana
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supporting information
p. 14950 - 14956
(2020/07/04)
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- ANTI-PARASITIC COMPOUNDS
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Provided are compounds, methods, and pharmaceutical compositions useful for treatment of parasites, e.g., Leishmania. For example, the compound may he represented by Ar—C(=NR1)NR2—A—X—Y—Het2, and pharmaceutically acceptable salts thereof. Ar may be an optionally substituted, aryl or nitrogen-containing heteroaryl. R1 and R2 may independently represent H, optionally substituted C1-C6 alkyl, or optionally substituted C3-C6 cycloalkyl. A may be a bond or an optionally substituted linking moiety comprising 1, 2, or 3 rings. Each ring in the optionally substituted linking moiety may independently be one of: aryl, cycloalkyl, heterocycloalkyl, and heteroaryl. X may be O, S, amide, or a bond. Y may be optionally substituted C1-C14 alkyl or optionally substituted C2-C14 alkenyl. Het2 may be an optionally substituted five-membered nitrogen-containing heteroaromatic ring comprising 1, 2, or 3 ring heteroatoms.
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Paragraph 00124
(2018/03/25)
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- Synthesis method of 2-amino-4-chloro-6-metoxyphenol
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The invention discloses a synthesis method of 2-amino-4-chloro-6-metoxyphenol, which belongs to the field of chemical synthesis. The method comprises the following steps of adding p-nitrophenol of nitrosonitric acid and sulfuric acid into phenol, adding methane chloride and anhydrous glacial acetic acid to obtain a mixture, then putting the mixture into a high-pressure autoclave, adding absolute ethyl alcohol and inputting hydrogen, performing pumping filtration to obtain filter residues after reaction, adding copper chloride into the filter residues, generating light green precipitation after adjusting pH through sodium hydroxide, filtering, washing the filter residues and drying to obtain the 2-amino-4-chloro-6-metoxyphenol.
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Paragraph 0004; 0007
(2016/11/14)
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- Reactions of aryl 5-substituted-2-thiophenecarboxylates promoted by 4-Z-C6H4O-/4-Z-C6H4OH in 20 mol % DMSO(aq). Effect of nucleophile on acyl-transfer reaction
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Nucleophilic substitution reactions of 5-XC4H2(S)C(O)OC6H3-2-Y-4-NO2 (1) promoted by 4-Z-C6H4O-/4-Z-C6H4OH in 20 mol % dimethyl sulfoxide (DMSO)(aq) have been studied kinetically. The reactions exhibited second-order kinetics with βacyl = -2.52 to -2.83, ρ(x) = 2.81-3.16, βnuc = 0.88-0.04 and βlg = -0.94, respectively. The results have been interpreted with an addition-elimination mechanism in which the nucleophilic attack occurs in the rate-determining step. Comparison with existing data reveals that the ratedetermining step changes from the second to the first step by the change in the nucleophile from R2NH/R2NH2+ to 4-Z-C6H4O-/4-Z-C6H4OH.
- Pyun, Sang Yong,Paik, Kyu Cheol,Han, Man So,Cho, Bong Rae
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p. 2810 - 2814
(2016/02/05)
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- A practical approach for regioselective mono-nitration of phenols under mild conditions
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Cu(NO3)2.3H2O was demonstrated to be an efficient, regioselective and inexpensive nitrating reagent for the synthesis of mono-nitro substituted phenolic compounds. 12 examples of different phenols were examined. Good yields (67-90%) have been achieved. ARKAT-USA, Inc.
- Chen, Ling-Yan,Liu, Tao,Zhou, Xiaokun,Sun, Zhihua
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- Elimination reactions of aryl furylacetates promoted by r 2NH-r2NH2 + in 70 mol% MeCN(aq). effects of β-aryl on the ketene-forming transition-state
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Ketene-forming elimination from 2-X-4-nitrophenyl furylacetates (1a-d) promoted by r2NH-r2NH2 + in 70 mol % MeCN(aq) has been studied kinetically. When X = Cl and NO2, the reactions exhibited second-order kinetics as well as Broensted β = 0.37-0.54 and |βlg| = 0.31-0.45. The Broensted β decreased with a poorer leaving group and |βlg| increased with a weaker base. The results are consistent with an E2 mechanism. When the leaving group was changed to a poorer one [X= H (1a) and OCH3 (1b)], the reaction mechanism changed to the competing E2 and E1cb mechanisms. A further change to the E1cb mechanism was realized for the reaction of 1a with i-Pr2NH/i-Pr2NH2 + in 70 mol % MeCN-30 mol % D2O. By comparing the kinetic results in this study with the existing data for ArCH2C(O)OC6H3-2-X-4-NO 2, the effect of the β-aryl group on the ketene-forming elimination was assessed.
- Pyun, Sang Yong,Kim, Ju Chang,Cho, Bong Rae
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supporting information
p. 2143 - 2147
(2014/12/10)
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- Fluoride-induced intermolecular excimer formation of bispyrenyl thioureas linked by polyethylene glycol chains
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New bispyrenyl thioureas linked by polyethylene glycol (PEG) chains, L1-L3, and methoxy benzene pyrene thiourea, L4, were synthesized. Upon binding with F- in CHCl3, L1-L3 exhibited strong excimer emission bands (IE) and weak monomer emission bands (IM), while L4 displayed the same intensity of both bands. However, little or no change was observed in fluorescence spectra of L1 upon adding OH-, AcO -, BzO-, H2PO4-, Cl -, Br-, and I-. Therefore, only F- induced the pyrene excimer formation. Job's plots showed 1/1 or 2/2 complexation of L1 with F-. Ratios of IE/IM of L1·F- complex were dependent on the concentration of L1, implying that the dimerization of L1 proceeded via the intermolecular excimer formation. Among L1-L4, L1 possessed the highest binding constant and sensitivity toward F- implying the importance of the linking PEG chain. L1 was demonstrated to be an excellent probe for F- in CHCl3 with the detection limit as low as 46.2 μg/L.
- Thongkum, Duangrat,Tuntulani, Thawatchai
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experimental part
p. 8102 - 8109
(2011/10/30)
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- A probable hydrogen-bonded meisenheimer complex: An unusually high S NAr reactivity of nitroaniline derivatives with hydroxide ion in aqueous media
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Observations show that nitroanilines exhibit an unusually high S NAr reactivity with OH- in aqueous media in reactions that produce nitrophenols. SNAr reaction of 4-nitroaniline (2a) in aqueous NaOH for 16 h yields 4-nitrophenol (4a) quantitatively, whereas a similar reaction of 4-nitrochlorobenzene (1a) gave 4a in 2% yield together with recovered 1a in 97%, suggesting that the leaving ability of the NH2 group far surpasses that of Cl under these conditions. An essential feature of SNAr reactions of nitroanilines is probably that the NH2 leaving group participates in a hydrogen-bonding interaction with H 2O. Density functional theory (DFT) calculations for a set of 4-nitroaniline, OH-, and H2O suggest a possible formation of a Meisenheimer complex stabilized by hydrogen-bonding interactions and a six-membered ring structure. The results obtained here contrast with conventional SNAr reactivity profiles in which nitroanilines are nearly unreactive with nucleophiles in organic solvents.
- Imoto, Mitsutaka,Matsui, Yasunori,Takeda, Motonori,Tamaki, Akihiro,Taniguchi, Hisaji,Mizuno, Kazuhiko,Ikeda, Hiroshi
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experimental part
p. 6356 - 6361
(2011/10/05)
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- TRPV4 ANTAGONISTS
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The present invention relates to quinoline analogs, pharmaceutical compositions containing them and their use as TRPV4 antagonists.
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Page/Page column 42
(2011/10/13)
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- Zeolite H-Y-supported copper(II) nitrate: A simple and effective solid-supported reagent for nitration of phenols and their derivatives
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Highly regiospecific mononitration of phenols and substituted phenols is accomplished by employing copper(II) nitrate supported on a catalytic amount of zeolite H-Y in a solid state. Copyright Taylor & Francis Group, LLC.
- Lalitha,Sivakumar
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p. 1745 - 1752
(2008/09/20)
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- Nitration of some aromatic compounds by sodium nitrate in the presence of benzyltriphenylphosphonium peroxodisulfate
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A simple, mild, and regioselective method for the nitration of some aromatic compounds using sodium nitrate in the presence of benzyltriphenylphosphonium peroxodisulfate in acetonitrile as solvent is reported. Mild reaction conditions and good to excellent yields of the products are the noteworthy advantages of the method. Copyright Taylor & Francis Group, LLC.
- Tajik, Hassan,Zolfigol, Mohammad Ali,Albadi, Jalal,Eslami, Ramin
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p. 2771 - 2776
(2008/02/12)
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- Surfactant-mediated solvent-free dealkylative cleavage of ethers and esters and trans-alkylation under neutral conditions
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A simple, surfactant-mediated, one-pot, solvent-free dealkylative cleavage of aryl ethers and esters followed by subsequent optional trans-alkylation under essentially neutral conditions has been developed.
- Bhattacharya, Apurba,Patel, Nitin C.,Vasques, Tomas,Tichkule, Ritesh,Parmar, Gaurang,Wu, Jiejun
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p. 565 - 567
(2007/10/03)
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- Nitration of substituted phenols by different efficient heterogeneous systems
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Nitration of substituted phenols were carried out by the mixture of sodium nitrite and wet SiO2 (50% w/w) in the presence of four different efficient heterogeneous systems: 1) oxalic acid dihydrate (I), 2) sodium hydrogen sulphate (II), 3) aluminum hydrogen sulphate (III) and 4) silica sulphuric acid (IV) in CH2Cl2 at room temperature and high yields. Optimum conditions for theses systems and the regioselectivities of the reactions are reported.
- Habibi, Davood,Zolfigol, Mohammad Ali,Shiri, Morteza,Sedaghat, Abdolmajid
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- Mild cleavage of aryl mesylates: Methanesulfonate as potent protecting group for phenols
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A mild protocol for the chemoselective deprotection of aryl methanesulfonates is described. The transformation can be conducted on highly functionalized substrates and renders the methanesulfonate a useful, previously underutilized protecting group for phenols.
- Ritter, Tobias,Stanek, Kyrill,Larrosa, Igor,Carreira, Erick M.
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p. 1513 - 1514
(2007/10/03)
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- Regio-selective mono nitration of phenols with ferric nitrate in room temperature ionic liquid
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The mono nitration of phenols with ferric nitrate has been achieved in high regio-selectivities in 1-3 h at 30-60°C using the ionic liquid 1,3-di-n-butylimidazolium tetraflouroborate [bbim]BF4 as the solvent. In particular, excellent para selectives of the order of 76-86% for unsubstituted, ortho and meta-substituted phenols were observed.
- Rajagopal,Srinivasan
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p. 961 - 966
(2007/10/03)
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- Rates of reductive elimination of substituted nitrophenols from the (indol-3-yl)methyl position of indolequinones
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A series of indolequinones bearing substituted nitrophenols on the (indol-3-yl)methyl position was synthesised. The nitrophenol leaving groups were appropriately substituted to give a wide range (4 units) in phenolic pKa value. The rate of redu
- Swann,Moody,Stratford,Patel,Naylor,Vojnovic,Wardman,Everett
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p. 1340 - 1345
(2007/10/03)
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- Nitration of electron-rich aromatic compounds by cerium ammonium nitrate coated on silica
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Treatment of electron-rich aromatic derivatives with cerium (IV) ammonium nitrate coated on silica (CANSio2) affords nitro aromatic compounds. The scope and the limitation of this reaction are discussed.
- Grenier, Jean-Luc,Catteau, Jean-Pierre,Cotelle, Philippe
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p. 1201 - 1208
(2007/10/03)
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- Hydroxylation of Nitroarenes with Alkyl Hydroperoxide Anions via Vicarious Nucleophilic Substitution of Hydrogen
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Rhone-Poulenc Polska Ltd., ul. Grzybowska 80/82, 00-844 Warszawa, Poland Garbo- and heterocyclic nitroarenes react with anions of tert-butyl and cumyl hydroperoxides in the presence of strong bases to form substituted o- and p-nitrophenols. The reaction usually proceeds in high yields and is of practical value as a method of synthesis and manufacturing of nitrophenols. Orientation of the hydroxylation can be controlled to a substantial extent by selection of the proper conditions. Basic mechanistic features of this process were clarified.
- Makosza, Mieczyslaw,Sienkiewicz, Krzysztof
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p. 4199 - 4208
(2007/10/03)
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- The nitration of electron-rich aromatics
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The successful mononitration of a variety of electron-rich aromatic substrates is reported, employing either nitronium tetrafluoroborate or 'claycop' as the nitrating agent. Dinitration of four of the substrates was achieved when employing nitronium tetrafluoroborate. Several of the products have previously been prepared only by indirect methods.
- Dwyer,Holzapfel
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p. 7843 - 7848
(2007/10/03)
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- Effect of Topologically Controlled Coulombic Interactions on the Dynamic Behavior of Photoexcited Nitrophenyl Alkyl Ethers in the Presence of Tertiary Amines with Limited Motion Freedom
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Time-resolved electronic absorption spectroscopy has been successfully applied to clarify the mechanism of the "abnormal" photochemical cleavage of 4-nitrophenyl piperidinoaikyl ethers induced by controlled Coulombic disturbance of the "normal" electronic distribution of the radical anion intermediate. Thus, photolysis of 1-piperidino-2-(2-methoxy-4-nitrophenoxy)ethane (a system with an amine with limited freedom of motion) in acetonitrile leads to C-O bond photocleavage in a relatively slow process (k ≈ 4 × 105 s-1) from intermediate species that show radical-ion pair behavior. Systems with higher freedom of motion of the amine moiety, such as 1-piperidino-5-(2-methoxy-4-nitrophenoxy)pentane or 4-nitroveratrole 4- triethylamine, show the intermediate radicalion pairs mainly evolving to reduction products, probably a result of intermediates with geometries not allowed for the system with limited freedom of motion of the amine.
- Gonzalez-Blanco, Roberto,Bourdelande, Jose L.,Marquet, Jordi
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p. 6903 - 6910
(2007/10/03)
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- Topologically Controlled Coulombic Interactions, a New Tool in the Developing of Novel Reactivity. Photochemical and Electrochemical Cleavage of Phenyl Alkyl Ethers
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The hypothesis that a specific placement of a positive charge would dramatically alter the behavior of a charged intermediate has been tested.Phenyl ethers substituted by electron-attracting groups do not undergo reductive fragmentation.However, related α-piperidino-ω-(4-substituted-phenoxy)alkanes give alkyl ether photocleavage when the linker between the redox centers is short, or the usual substitution-reduction photochemistry when it is long.Mechanistic experiments suggest that the photofragmentation process operates through space intramolecular electron transfer to the triplet aromatic chromophore and that a coplanar relative orientation of the alkyl ether bond and the phenyl ring is compulsory for the photofragmentation to be observed.Configuration interaction AM1 calculations justify the described facts, indicating that the fragmentation process is only operative when a Coulombic stabilization of a ?* intramolecular electron transfer excited state is produced.Electrochemical studies carried out with the corresponding quaternary salts (intermolecular generation of the phenyl ether radical anion) confirm the conclusions derived from the photochemical experiments.
- Marquet, Jorge,Cayon, Eduard,Martin, Xavier,Casado, Francisco,Gallardo, Iluminada,et al.
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p. 3814 - 3825
(2007/10/02)
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- Pyrimidinedione derivatives and antiarrhythmic agents containing same
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Pyrimidinedione derivatives of the formula: STR1 wherein R1 and R2 is so linked with each other as to make an alkylene chain and thus form a heterocyclic structure, A, R3, R4, X1, X2 and X3 are substituents, respectively, and n is 2 or 3 have a basic backbone in which a phenyl group part and a pyrimidinedione part are linked by a structure comprising an alkyl chain and a heterocyclic ring having two nitrogen atoms. These compounds are useful for a medical treatment of cardiac arrhythmias.
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- Pyrimidinedione compounds, method of producing the same and antiarrythmic agents containing the same
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A pyrimidinedione derivative compound has a basic backbone in which a phenyl group part and a pyrimidinedione part are linked by a structure comprising an alkyl chain containing at least two nitrogen atoms. The pyrimidinedione derivative is useful for a medical treatment of cardiac arrhythmias.
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- STUDIES ON THE TWO-PHASE NITRATION OF PHENOLS (part 2)
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Gas phase Ionization Potentials can be correlated with solution Oxidation Potentials for phenols and used to predict the likelihood of successful nitration using the two-phase procedure.The interaction of steric and electronic effects then determines the sites of nitration by radical recombination of the phenoxy radical and NO2.Nitration of dioxybenzenes may give insights into the nitration mechanism.
- Thompson, Malcolm J.,Zeegers, Petrus J.
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p. 2661 - 2674
(2007/10/02)
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- Comparative Toxicities and Analgesic Activities of Three Monomethylated Analogues of Acetaminophen
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Three monomethylated derivatives of 4'-hydroxyacetanilide (acetaminophen) were prepared in order to compare their cytotoxic potential and analgesic activity with that of acetaminophen.Only 4'-hydroxy-methylacetanilide (N-methylacetaminophen) was devoid of cytotoxic effects to hepatic tissue of mice.Results of comparative tissue distribution studies and metabolism studies both in vivo and in vitro in mice indicate that the disposition of N-methylacetaminophen is similar to that of acetaminophen except that it is not oxidized to a toxic metabolite.In contrast, 3'-methyl-4'-hydroxyacetanilide (3-methlacetaminophen) is as hepatotoxic as acetaminophen in mice while 2'-methyl-4'-hydroxyacetanilide (2-methylacetaminophen) is less hepatotoxic.The analgesic potency of the analogues seems to parallel their hepatotoxic potential, and both activities parallel the oxidation potentials in this series of compounds.
- Harvison, Peter J.,Forte, Anthony J.,Nelson, Sidney D.
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p. 1737 - 1743
(2007/10/02)
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- PHOTOCHEMICAL HYDROLYSIS OF SOME NITROPHENYL ACETATES
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Nitro substituent exhibits a meta-activating effect on the course of photochemical hydrolysis of phenyl acetates since UV photolysis of isomeric 4- and 3-nitrophenyl acetates in neutral aqueous solution leads to the formation of the corresponding phenols with quantum yields 0.002 and 0.006, respectively; 2-methoxy-4-nitro- and 2-methoxy-5-nitrophenyl acetates showed still greater difference in their photochemical reactivity ( Φr 0.002 and 0.129, respectively).Quenching of the photohydrolysis of the latter compound with 2,4-hexadienoic acid indicates the participation of a triplet state with the effective lifetime of 0.15 μs.The photoreaction is accelerated in acidic media which means that one of the early photochemical steps is the protonation of the excited state.No incorporation of 18O into the product molecule was observed after the photolysis of 2-methoxy-5-nitrophenyl acetate in H218O, which is an unambiguous evidence that the photoreaction proceeds as a light-induced hydrolysis of the ester bond.
- Kuzmic, Petr,Pavlickova, Libuse,Soucek, Milan
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p. 1293 - 1300
(2007/10/02)
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- NUCLEOPHILIC RING CLEAVAGE OF CROWN ETHERS, NOVEL METHOD FOR BUILDING UP CROWN ETHER RINGS
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The crown ether rings in 4-nitrobenzo-15-crown-5 and -18-crown-6 are cleaved by aqueous alkali affording long chain substituted pyrocatechols which proved to be good starting material for constructing crown ether rings other than the original one.
- Agai, Bela,Bitter, Istvan,Hell, Zoltan,Szoelloesy, Aron,Toeke, Laszlo
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p. 2705 - 2708
(2007/10/02)
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- Synthesis of Nitrohydroxyxanthones and Oxidative Coupling of Phenols Using Cerium(IV) Ammonium Nitrate
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Nitration of 1-hydroxyxanthone and oxidative coupling of phenol and o-methoxyphenol by cerium(IV)ammonium nitrate (CAN) have been reported for the first time.The reaction in each case leads to the formation of nitro-bis-phenols along with nitrophenols.
- Chaudhuri, Kakoli (nee-Chakrabarty),Chawla, H. Mohindra
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p. 1277 - 1279
(2007/10/02)
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- KINETICS AND MECHANISM OF SUBSTITUTIVE NITRATION OF GUAIACOL DERIVATIVES WITH DILUTE NITRIC ACID
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The kinetics of the nitration reactions of a series of compounds which model the guaiacylpropane unit of lignin (vanillin, vanillic acid, and vanillic alcohol) to dinitroguaiacol by dilute nitric acid and aqueous sulfuric-nitric acid mixtures were investigated.It was shown that the substitution of the functional groups at the para position to the hydroxyl by a nitro group does not include an intermediate nitrosation stage but takes place by a free-radical mechanism, involving the formation and dissociation of nitroquinolide compounds.
- Bazanova, G. V.,Stotskii, A. A.
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p. 1845 - 1850
(2007/10/02)
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