- Synthetic route to isotopically labelled-oxamate
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Since none of the available methods was suitable for the synthesis of isotopically labelled oxamate, a new procedure has been developed in our laboratory, based on the known procedures, but with substantial modifications. The method is convenient and gives reproducibly 17% yield based on KCN used. The strategy is considered suitable for labelling oxamate with 15N and 13C or 14C when starting with labelled KCN and can be easily modified for the synthesis of 18O-carbonyl-labelled oxamate. Copyright 2011 John Wiley & Sons, Ltd. Synthesis route to sodium oxamate labelled with various isotopes has been proposed. Copyright
- Siwek, Agata,Trotsko, Nazar,Wujec, Monika,Kaminski, Rafal,Paneth, Piotr
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Read Online
- Oxidative Coupling of Diazo and NH4I: A Route to Primary Oxamates and α-Ketoamides
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A simple and efficient method has been developed for the preparation of primary oxamates and α-ketoamides through the oxidative coupling of diazo compounds and NH4I. Under the optimized reaction conditions, a range of diazoesters and α-diazoketones was explored, and the corresponding products were obtained in moderate to good yields. This protocol is metal-free, is performed under mild conditions, has a wide substrate scope, and offers operational simplicity.
- Fang, Shangwen,Li, Jingjing,Wan, Xiaobing,Wang, Hanghang,Zhao, Yanwei,Zheng, Yonggao
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supporting information
p. 3050 - 3058
(2020/03/23)
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- Method for preparing oxamide ester
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The invention discloses a method for preparing oxamide ester. A diazonium ester compound and ammonium iodide are adopted as reaction substrates, t-butylhydroperoxide (TBHP) is adopted as an environment-friendly oxidant under the condition of having no transition metal and alkali, and the oxamide ester is obtained through an oxidative coupling reaction in an organic solvent. Compared with the priorart, the method has the following advantages that the range of the reaction substrates is wide, reaction conditions are mild, the operation is simple, and the environment is protected. According to the method, TBHP is used as the oxidant, tert-butanol and water are produced after the reaction, the use of oxidants such as iodobenzene acetate and sodium hypochlorite is avoided, no harm is caused tothe environment, and the requirements of contemporary environment-friendly chemistry are met. In addition, the method can be used for post-modification of natural active molecules, such as cholesterol and epiandrosterone, a final target product with a high yield can be obtained, and a foundation is laid for practical application.
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Paragraph 0022-0023
(2019/09/05)
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- Metal-, Photocatalyst-, and Light-Free Direct C-H Acylation and Carbamoylation of Heterocycles
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Direct C-H acylations and carbamoylations of heterocycles can now be readily achieved without requiring any conventional metal, photocatalyst, electrocatalysis, or light activation, thus significantly improving on sustainability, costs, toxicity, waste, and simplicity of the operational procedure. These mild conditions are also suitable for gram-scale reactions and late-stage functionalizations of complex molecules, including pharmaceuticals, N,N-ligands, and light-sensitive molecules.
- Westwood, Matthew T.,Lamb, Claire J. C.,Sutherland, Daniel R.,Lee, Ai-Lan
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supporting information
p. 7119 - 7123
(2019/09/03)
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- Mild and selective heterogeneous catalytic hydration of nitriles to amides by flowing through manganese dioxide
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A sustainable flow chemistry process for the hydration of nitriles, whereby an aqueous solution of the nitrile is passed through a column containing commercially available amorphous manganese dioxide, has been developed. The product is obtained simply by concentration of the output stream without any other workup steps. The protocol described is rapid, robust, reliable, and scalable, and it has been applied to a broad range of substrates, showing a high level of chemical tolerance.
- Battilocchio, Claudio,Hawkins, Joel M.,Ley, Steven V.
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supporting information
p. 1060 - 1063
(2016/10/17)
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- Extremely simple but long overlooked: Generation of α-Azido alcohols by hydroazidation of aldehydes
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Discovered by accident: Just because an example of a simple substructure cannot be found in literature does not mean that corresponding compounds are not readily accessible. α-Azido alcohols like 1-azidoethanol have now been prepared and isolated. Copyright
- Banert, Klaus,Berndt, Christian,Firdous, Samia,Hagedorn, Manfred,Joo, Young-Hyuk,Rueffer, Tobias,Lang, Heinrich
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supporting information; experimental part
p. 10206 - 10209
(2011/02/27)
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- Dibutyltin oxide catalyzed aminolysis of oxalate to carbamate, oxamate and derivatives of imidazolidine trione
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Catalytic aminolysis of oxalates by simple and substituted ureas has been shown to give carbamates, oxamates and derivatives of imidazolidine trione. Various substituted ureas and oxalates were screened to verify the applicability of the protocol. The rol
- Kunde, Lalita B.,Kalyani, Vishwanath S.,Gupte, Sunil P.
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experimental part
p. 402 - 407
(2010/08/06)
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- DECOMPOSITION PRODUCTS OF HALONITROACETIC ACID DERIVATIVES
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The halonitro group O2NCHX of chloro- and bromonitroacetic acid derivatives underwent reduction to H2NCO upon boiling.The same derivatives decomposed to oxalic acid upon long storage.Likely chemical transformation pathways are discussed. Keywords: chloro- and bromonitroacetic acids, reduction, oxalic acid, amides.
- Yurtanov, A. I.
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p. 120 - 122
(2007/10/02)
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- Derivatives of 4-(2,4-difluoro-biphenylyl)-2-methyl-4-oxo-butanoic acid
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This invention relates to substances represented by Formula (I), wherein X stands for either OR in which R is an alkyl of 1 to 4 carbon atoms, or NHR in which R is an alkyl of 1 to 4 carbon atoms, or a (CH2)nNR'2 group wherein n is 2 or 3 while R' is a methyl or ethyl group; eventually X may represent morpholinyl. Also considered are salts of 4-(2,4-difluorobiphenylyl)-2-methyl-4-oxobutanoic acid with appropriate inorganic or organic bases represented by Formula (II) wherein B is either an alkaline metal cation, alkaline earth cation, cyclohexylamine cation, or lysine cation. Said substances are characterized by anti-inflammatory properties comparable to (and greater than) the initial acid while simultaneously said modifications of their physico-chemical properties broaden the possibilities of their therapeutic application.
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- SPIRO NITROGEN-BRIDGED HETEROCYCLIC COMPOUNDS
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The invention relates to novel compounds (I) for treating diseases of the central and peripheral nervous system: STR1 including enantiomers, racemates and acid addition and quaternary salts thereof, wherein one of X and Y is O and the other of X and Y is N; Q is (CH 2) n or C(CH. sub.3) 2 where n is 1, 2 or 3 and the bridge--Q--is attached at one end to position 1 and at the other end to position 4 or 5, and R° is hydrogen, methyl or hydroxyl; in the moiety STR2 the line connecting Z and Y signifies a double bond when X--Z is O--C--R and Y is N, and a single bond when X--Z is N=C--R and Y is O; Z is C--R wherein R is selected from hydrogen, NH 2, NH-R" (R"=C 1-6-alkyl) , N(R") 2, R", C 2-6-alkenyl, C 2-6-alkynyl, C 3-7-cycloalkyl, R" substituted by hydroxy or by 1-6 halogen atoms, R"O-C 1-6-alkyl, carboxy-C 1-6-alkyl, R"OCO-C 1-6-alkyl, amino-C 1-6-alkyl, R"NH-C 1-6-alkyl, (R") 2 N-C 1-6-alkyl, 2-oxo-pyrrolidin-1-ylmethyl, aryl, diarylmethylol, and R" substituted by one or two aryl groups, wherein aryl denotes phenyl optionally substituted by 1-3 halogens, R", R"O and(or) CF 3. Also claimed are compounds wherein the line connecting Z and Y signifies the absence of a bond, X is O, Z is H and Y is NH 2, NO 2 or N 3. "
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- PHOTOCHEMICAL REACTION OF NAPHTHYL α-NITROACRYLATES
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Photolysis of 2-nitro-3-(1-naphthyl)acrylates (1) in acetone gave novel naphthofuran-2-carboxylates (2) and 2-(alkoxyoxalylamino-methylene)naphthalen-1-ones (3). 2-Nitro-3-(2-naphthyl)acrylate also produced the furan derivative 2 on irradiation.A mechanism for this new photorearrangement reaction is described.KEYWORDS -- photochemical rearrangement; naphthyl α-nitroacrylate; naphtholfuran-2-carboxylate; 2-(ethoxyoxalylaminomethylene)naphthalen-1-one; α-keto-β-hydroxyiminoester
- Hirotani, Seiko,Zen, Shonosuke
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p. 2944 - 2947
(2007/10/02)
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- Purines, Pyrimidines, and Imidazoles. Part 53. Synthesis of Some 5-Halogeno-analogues of Metiamide and Cimetidine
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Ethyl 5-chloroimidazole-4-carboxylate has been prepared by diazotisation of ethyl 5-amino-1-(di-O-isopropylidene-α- or α,β-D-mannofuranosyl)imidazole-4-carboxylate, reaction of the diazonium salt with copper(I) chloride and removal of the 1-substituent with hydrochloric acid, or by similar conversion of ethyl 5-amino-1-t-butylimidazole-4-carboxylate to ethyl 1-t-butyl-5-chloroimidazole-4-carboxylate, and removal of the t-butyl group with hydrogen bromide.Ethyl 5-fluoroimidazole-4-carboxylate has been prepared from ethyl 5-amino-1-t-butylimidazole-4-carboxylate by diazotisation and photolysis in the presence of tetrafluoroboric acid.Ethyl 5-chloroimidazole-4-carboxylate and ethyl 5-fluoroimidazole-4-carboxylate have been converted into the corresponding alcohols by reaction with lithium aluminium hydride. 5-Chloro-4-(hydroxymethyl)imidazole has also been prepared by electrolysis of 5-chloroimidazole-4-carboxylic acid at mercury cathode. 5-Chloroimidazole has been converted into the 5-chloroimidazolyl analogues of metiamide and cimetidine by a sequence of reactions, and 5-fluoroimidazole has been similarly converted into the 5-fluoro-analogue of metiamide.The metiamide and cimetidine analogues were found to be histamine H2-receptor antagonists.
- Brown, Tom,Shaw, Gordon,Durant, Graham J.
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p. 2310 - 2315
(2007/10/02)
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