- A dichlorination-reductive-dechlorination route to N-acetyl-2-oxazolone
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We have shown that sulfuryl chloride is an efficient reagent for the conversion of 2-oxazolidinone into the dichloro derivative, N-acetyl-4,5- dichloro-2-oxazolidinone. Subsequent Zn/AcOH reductive dehalogenation of this trans-dichloride gives N-acetyl-2-oxazolone. The dichloride was previously reported as an undesired side product in the preparation of N-acetyl-2-oxazolone from the monochloro oxazolidinone. In our hands, the dichloride is a key intermediate in a new synthesis of 2-oxazolone, that avoids the use of chlorine gas. Georg Thieme Verlag Stuttgart.
- Gaenzler, Faith Corbo,Smith, Michael B.
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- A convenient antibiotic indicator in the ozone treatment of wastewaters. An experimental and theoretical study
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N-Acetyl-oxazolidin-2-one has been found to be a convenient indicator in the removal of nitroimidazole-type antibiotic contaminants in wastewaters by ozone since it is the unique product generated in the treatment of waters containing metronidazole, and it is stable against further ozonation in the experimental conditions used. The oxidative conditions imposed by the reaction do not allow isolation of any by-products, nor other stable subproducts. High-performance liquid chromatography coupled with electrospray ionization-time-of-flight mass spectrometry (HPLC-ESI-TOF(MS)) revealed the presence of simple derivatives of both metronidazole and N-acetyl-oxazolidin-2- one, thus indicating that both products are unambiguously connected and that, possibly, a unique reaction pathway would take place in this case. A feasible mechanism for this transformation has then been postulated, which is supported by several experimental findings such as TOC analysis and nitrate titration, both correlating well with the proposed transformation. Furthermore, this mechanism has been evaluated by DFT/B3LYP calculations, showing that the observed product is readily obtained thanks to the high exothermicity displayed by the metronidazole ozonation process.
- Mota, Antonio J.,Prados-Joya, Gonzalo,Arraez-Roman, David,Sanchez-Polo, Manuel,Robles, Rafael,Ferro-Garcia, M. Angeles,Rivera-Utrilla, Jose
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Read Online
- One-Pot Synthesis of α-Ketoamides from α-Keto Acids and Amines Using Ynamides as Coupling Reagents
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A one-pot strategy for α-keto amide bond formation have been developed by using ynamides as coupling reagents under extremely mild reaction conditions. Diversely structural α-ketoamides were afforded in up to 98% yield for 36 examples. This reaction features advantages such as practical coupling procedure, wide functional group tolerance, and extremely mild conditions and has potential applications in synthetic and medicinal chemistry.
- Ma, Jianting,Cui, Xue,Xu, Junyu,Tan, Yinfeng,Wang, Yan,Wang, Xuesong,Li, Youbin
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supporting information
p. 3661 - 3667
(2022/02/07)
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- An eco-friendly and highly efficient route for N-acylation under catalyst-free conditions
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An eco-friendly, simple, mild, chemoselective and highly efficient procedure for the acylation of primary and secondary amine function in various structurally and electronically aliphatic and aromatic compounds affording their corresponding N-Ac derivatives is developed. Mild conditions, simplicity and easier work-up are the main advantages of this method.
- Ouarna, Souad,K'tir, Hacène,Lakrout, Salah,Ghorab, Hamida,Amira, A?cha,Aouf, Zineb,Berredjem, Malika,Aouf, Nour-Eddine
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p. 913 - 919
(2015/10/28)
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- Enantioselective multicomponent synthesis of fused 6-5 bicyclic 2-butenolides by a cascade heterobicyclisation process
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The successive coupling of an alkoxy(aryl/heteroaryl)carbene complex of chromium with either a ketone or an imide lithium enolate and then a 3-substituted (H, TMS, PhCH2, PhCH2CH2, Me) propargylic organomagnesium reagent h
- Suero, Marcos G.,De La Campa, Raquel,Torre-Fernandez, Laura,Garcia-Granda, Santiago,Florez, Josefa
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supporting information; experimental part
p. 7287 - 7295
(2012/07/17)
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- Synthesis of N-Acyl carbamates and oxazolidinones using HClO 4-SiO2 as catalyst under solvent-free conditions
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Silica supported perchloric acid catalyzes efficiently the reaction of carbamates and oxazolidinones with anhydrides in the presence of silica sulfuric acid under solvent-free conditions. All the reactions were done at room temperature and the N-acyl carb
- Yang, Li Juan,Yang, Yuping,Dong, Ruoyi
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experimental part
p. 1085 - 1087
(2011/12/16)
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- Short communication: Silica sulfuric acid: A versatile and reusable heterogeneous catalyst for the synthesis of N-ACYL carbamates and oxazolidinones under solvent-free conditions
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Silica sulfuric acid catalyzes efficiently the reaction of carbamates and oxazolidinones with anhydrides under solvent-free conditions. All the reactions were done at room temperature and the N-acyl carbamates and oxazolidinones were obtained with high yi
- Wu, Liqiang,Yang, Xiaojuan,Yan, Fulin
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experimental part
p. 151 - 155
(2012/05/20)
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- 2-Dienylphenacyloxazolones and an intramolecular Diels-Alder approach to the A-B-C ring system of phenanthridone alkaloids
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A general route to the A-B-C ring system of phenanthridone alkaloids is available by acylation of 2-oxa-zolone with a 2-butadienylbenzoic acid derivative, followed by an intramolecular Diels-Alder reaction and hydrolysis.
- Gaenzler, Faith Corbo,Guo, Chen (Lisa),Zhang, Yun-Wei,Azab, Mohammad E.,Salem, Mounir A.I.,Fan, Dong Ping,Smith, Michael B.
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scheme or table
p. 8781 - 8785
(2009/12/26)
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- DCC/DMAP-Mediated Coupling of Carboxylic Acids with Oxazolidinones and Thiazolidinethiones
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Dicyclohexylcarbodiimide and catalytic dimethylaminopyridine were successfully used in the coupling of carboxylic acids with oxazolidinones and thiazolidinethiones. The acylated products were obtained in good yields.
- Andrade, Carlos Kleber Z.,Rocha, Rafael O.,Vercillo, Otilie E.,Silva, Wender A.,Matos, Ricardo Alexandre F.
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p. 2351 - 2352
(2007/10/03)
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- N-Acylation of amides with acid anhydrides by way of dual activation using MgBr2·OEt2
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A new practical method for the N-acylation of amides is described. Acylation of various amides with acid anhydrides in the presence of MgBr2·OEt2 gave the corresponding N-acylamides in good to moderate yields. The present method is a
- Yamada, Shinji,Yaguchi, Setsuko,Matsuda, Kaori
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p. 647 - 651
(2007/10/03)
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- Topical compositions useful as skin penetration barriers
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Methods for preventing the penetration of toxic chemicals through the stratum corneum of the skin of a mammal are disclosed which employ, as a penetration prevention agent, at least one compound selected from the group consisting of compounds represented by the formula: wherein W1 is a divalent oxygen, sulfur or nitrogen radical, W2 and W3 are independently a divalent oxygen or sulfur radical, R' is an alkyl radical comprising from 1 to 4 carbon atoms, y is 0 or 1, R1 and R2 are alkyl radicals comprising from 1 to 10 carbon atoms and R and R3 are individually a hydrocarbyl radical containing from 1 to 20 carbon atoms or a heteroatom-substituted derivative thereof wherein at least one but not two adjacent carbon atoms may be replaced by a divalent oxygen or sulfur radical or by NR'', wherein R'' is hydrogen or R', n is an integer from 2 to 5 and compounds represented by the above formula in which the ring and/or R includes one to three carbon carbon double bonds.
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- Formation of N-Tributylstannyl Heterocycle from Bis(tributyltin) Oxide and ω-Haloalkyl Isocyanate. One-Pot Convenient Synthesis of 2-Oxazolidinones and Tetrahydro-2H-1,3-oxazin-2-one
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Novel types of compounds, N-tributylstannyl-2-oxazolidinone (4a) and tetrahydro-2H-1,3-oxazin-2-one (4b), are formed from the adduct of (n-Bu3Sn)2O (1) with ω-haloalkyl isocyanate (2), and the subsequent coupling reaction with alkyl halides gives a variety of N-substituted 2-oxazolidinones and tetrahydro-2-oxazinones in a one-pot procedure.Both the cyclization and the coupling reaction proceed quantitatively in the presence of HMPA which enhances the reactivity of the Sn-heteroatom bond by coordination.
- Shibata, Ikuya,Nakamura, Kenji,Baba, Akio,Matsuda, Haruo
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p. 853 - 859
(2007/10/02)
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- Azides. Part VIII. Thermolysis of ethyl azidoformate in acetic and propionic anhydrides: facilitation of intramolecular cyclization of the resultant carbethoxynitrene to 2-oxazolidinone
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The thermolysis of ethyl azidoformate in acetic and propionic anhydrides as solvent yielded the corresponding N-acyl-2-oxazolidinones (2a,b) in relatively significant yields.The other major products isolated were N-carboxyethyl-N,O-diacyl hydroxylamine (1a.b) and N,N,O-triacetyl hydroxylamine (3).The intramolecular cyclization is facilitated by the solvent.
- Ayyangar, N. R.,Brahme, K. C.,Srinivasan, K. V.
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p. 1463 - 1468
(2007/10/02)
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- Formation of N-Tributylstannyl-2-oxazolidone from (Bu3Sn)2O and 2-Chloroethyl Isocyanate
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N-Tributylstannyl-2-oxazolidone is formed from the reaction of (Bu3Sn)2O and 2-chloroethyl isocyanate in the presence of hexamethylphosphoric triamide, and reacts with electrophiles to give N-substituted 2-oxazolidones in good yields.
- Shibata, Ikuya,Baba, Akio,Matsuda, Haruo
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p. 1703 - 1704
(2007/10/02)
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- Carbonylation of β-Aminoethanols, Diols, and Diol Amines
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Oxazolidinones are prepared from the palladium-catalyzed carbonylation of β-aminoethanols under mild conditions.With N-alkyl-substituted substrates, conditions for double carbon monoxide incorporation to give morpholinediones have been discovered.Cyclic carbonates can be prepared from the carbonylation of diols.The carbonylation of N-phenyl-1-aminopropane-2,3-diol can give either the carbonate or oxazolidinone as the major product depending on the reaction conditions.
- Tam, Wilson
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p. 2977 - 2981
(2007/10/02)
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- A Novel Synthesis of 2-Substituted Oxazolines
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Thermal rearrangement of N-acyl-2-oxazolidones in the presence of calcium oxide has been shown to provide a new entry into 2-substituted oxazolines.
- Mundy, Bradford P.,Kim, Youseung
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p. 1221 - 1222
(2007/10/02)
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