- Production method of o/p-nitrophenetole
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The invention discloses a production method of o/p-nitrophenetole, which comprises the following steps: (1) adding o/p-nitrochlorobenzene and ethanol into a four-neck flask provided with a heating reflux matching device, then adding N-methylmorpholine, co
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Paragraph 0021-0035
(2021/06/09)
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- Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols
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N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.
- Annatelli, Mattia,Trapasso, Giacomo,Salaris, Claudio,Salata, Cristiano,Castellano, Sabrina,Aricò, Fabio
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supporting information
p. 3459 - 3464
(2021/05/24)
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- Aryl Ether Syntheses via Aromatic Substitution Proceeding under Mild Conditions
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In this study, mild conditions for aromatic substitutions during the syntheses of aryl ethers were developed. In the reaction conditions, the choices of solvent, base, and the sequence for the addition of the reagents proved important. A wide variety of alcohols were used directly as nucleophiles and smoothly reacted with aryl chlorides that possessed either a nitro or a cyano group at either the ortho- or para-position. Controlled experiments we performed suggested that the reaction underwent a charge-transfer process mediated by a combination of DMF and tert-BuOK.
- Ando, Shin,Tsuzaki, Marina,Ishizuka, Tadao
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p. 11181 - 11189
(2020/10/12)
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- Ligand-free Cu(ii)-catalyzed aerobic etherification of aryl halides with silanes: An experimental and theoretical approach
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Owing to their wide occurrence in nature and immense applications in various fields, the synthesis of aryl alkyl ethers has remained a focus of interest. In contrast to the conventional/traditional methods of etherification, herein, we have reported a more efficient method, which is better yielding and more general in application. The etherification of aryl halides by alkoxy/phenoxy silanes was catalyzed by copper acetate in the presence of cesium carbonate and oxygen in DMF at 145 °C. All the as-synthesized compounds were characterized via the 1H-NMR and 13C-NMR spectroscopic techniques. Density functional theory calculations using the B3LYP functional were performed to elucidate the reaction mechanism. The C-O coupling reaction between 2-nitroiodobenzene and tetramethoxysilane was used as a model reaction. The activation energy barriers for the generation of catalytic species (31.6 kcal mol-1) and the σ-bond metathesis (16.0 kcal mol-1), oxidative addition/reductive elimination (20.3 kcal mol-1), halogen atom transfer (19.2 kcal mol-1) and single electron transfer (SET) (29.5 kcal mol-1) mechanisms for the C-O coupling reaction were calculated. Calculations for the key reaction steps were repeated with the B3PW91, PBEH1PBE, wB97XD, CAM-B3LYP and mPW1LYP functionals. The formation of catalytic species via a single electron transfer reaction between tetramethoxysilane and copper acetate, formation of methoxy radicals and methoxylation of copper showed an overall energy barrier of 31.6 kcal mol-1, and therefore is the rate determining step.
- Ahmed, Muhammad Naeem,Ahmad, Khalil,Yasin, Khawaja Ansar,Farooq, Tayyaba,Khan, Bilal Ahmad,Roy, Soumendra K.
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p. 11316 - 11333
(2019/07/31)
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- Ipso-Nitrosation of arylboronic acids with chlorotrimethylsilane and sodium nitrite
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Nitroso compounds are versatile reagents in synthetic organic chemistry. Herein, we disclose a feasible protocol for the ipso-nitrosation of aryl boronic acids using chlorotrimethylsilane-sodium nitrite unison as nitrosation reagent system.
- Prakash, G.K. Surya,Gurung, Laxman,Schmid, Philipp Christoph,Wang, Fang,Thomas, Tisa Elizabeth,Panja, Chiradeep,Mathew, Thomas,Olah, George A.
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p. 1975 - 1978
(2014/04/03)
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- Decarboxylative etherification of aromatic carboxylic acids
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Decarboxylative Chan-Evans-Lam-type couplings are presented as a new strategy for the regiospecific construction of diaryl and alkyl aryl ethers starting from easily available aromatic carboxylic acids. They allow converting various aromatic carboxylate salts into the corresponding aryl ethers by reaction with alkyl orthosilicates or aryl borates, under aerobic conditions in the presence of silver carbonate as the decarboxylation catalyst and copper acetate as the cross-coupling catalyst.
- Bhadra, Sukalyan,Dzik, Wojciech I.,Goossen, Lukas J.
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p. 9938 - 9941
(2012/08/08)
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- Iodine-mediated cyclisation of thiobenzamides to produce benzothiazoles and benzoxazoles
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Synthesis of benzothiazoles by reaction of iodine with thiobenzamides, which do not possess an ortho alkoxy or ester group, is described. The unlikely synthesis of benzoxazoles from reaction of 2-alkoxythiobenzamides with iodine is also reported.
- Downer-Riley, Nadale K.,Jackson, Yvette A.
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p. 10276 - 10281
(2008/02/13)
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- Chemoselective O-methylation of phenols under non-aqueous condition
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Chemoselective O-methylation of substituted phenols takes place in dry. tetrahydrofuran (THF) in the presence of LiOH.H2O and dimethylsulfate (DMS). Quantitative methyl transfer from DMS preserves the atom economy.
- Basak, Anindita,Nayak, Mrinal K.,Chakraborti, Asit K.
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p. 4883 - 4886
(2007/10/03)
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- Generation of Sulfenate Salts via Ipso-substitution of Azaheterocyclic Sulfoxides. First Preparation and Characterization of Sodium 2-Pyridinesulfenate
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2-Alkyl- or 2-aryl-sulfinylpyridine N-oxides undergo ipsosubstitution reaction with sodium ethoxide to afford sodium sulfenates which were converted soon to the corresponding sulfinates upon contact with oxygen.Sodium 2-pyridinesulfenate was prepared and characterized by FT-IR as the first example of stable sulfenate.
- Furukawa, Naomichi,Konno, Yasuo,Tsuruoka, Masayuki,Fujihara, Hisashi,Ogawa, Satoshi
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p. 1501 - 1504
(2007/10/02)
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