- A simple method for the functionalization of naked amino hydroxymethylenebisphosphonic acids via a carbamate bond
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A simple and efficient procedure for the synthesis of alkylcarbamate hydroxymethylenebisphosphonic acids is described. Hydroxylated compounds are activated with carbonyldiimidazole and coupled to naked amino hydroxymethylenebisphosphonic acids.
- Lecouvey, Marc,Leroux, Yves
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Read Online
- Synthesis and properties of polymeric materials prepared by polymerization of epoxy oligomers with N,N′-carbonyldiimidazole transformation products
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The reaction of N,N′-carbonyldiimidazole with ethanol and epoxy oligomers of diphenylolpropane diglycidyl ether and 4,4′- bis(glycidylamino)-3,3′-dichlorodiphenylmethane was studied by gas chromatography-mass spectrometry and differential scanning calorimetry. From these oligomers and N,N′-carbonyldiimidazole transformation products, epoxy polymers were synthesized, and their physicomechanical and adhesion properties were determined. Pleiades Publishing, Ltd., 2012.
- Fedoseev,Glushkov,Gorbunov,Derzhavinskaya,Oshchepkova
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Read Online
- Palladium-Catalyzed Oxidative C–H Alkoxycarbonylation of Arenes with Alkylcarbazates Directed by N-Heterocyclic Substituents
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With alkyl carbazates as the green ester source, a novel palladium-catalyzed oxidative free radical carbonylative transformation of the C–H bond on aromatic rings to produce esters has been developed. Good yields of the corresponding products have been obtained with wide functional group tolerance and excellent regioselectivity. A variety of alkyl carbazates are found to be suitable reactants for the ortho-alkoxycarbonylation on the aromatic ring.
- Yogesh Kumar, Gujjenahalli Ramalingaiah,Begum, Noor Shahina
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supporting information
p. 4698 - 4704
(2020/07/04)
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- Method for preparing spiro2-diazido-indoline
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The invention provides a method for preparing a compound shown in the formula II (please see the formula in the description). The method includes the following step of making indole shown in the formula I (please see the formula in the description) react with a precursor and ceric ammonium nitrate in the inert atmosphere so that spiro2-diazido-indoline can be obtained, wherein the precursor can provide azide groups. In the formula I and the formula II, R1 is selected from at least one of hydrogen, an alkyl group of C1-C5, alkoxy of C1-C5, F, Br and Cl; R2 is an alkyl group of C1-C5; Boc represents t-butyloxycarboryl. The precursor is sodium azide or trimethylsilyl azide. The mole ratio of indole shown in the formula I to the precursor to ceric ammonium nitrate is 1:(2-4):(4-8). According to the simple method, the two azide groups are introduced to the organic molecule, and in other words, spiro2-diazido-indoline is effectively prepared under the effects of the precursor capable of providing the azide groups and ceric ammonium nitrate with indole of different structures as the raw material. The raw material is easy to prepare, the reaction condition is gentle, operation is easy and convenient, and yield can reach 45% at most.
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Paragraph 0033; 0034; 0035
(2016/10/09)
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- Preparation method of spiro-2-azidoindoline
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The invention provides a preparation method of a compound represented by the formula (III) or formula (IV). According to the preparation method, in an inert atmosphere, indoles represented by the formula (I) or (II), a precursor that can provide azido groups, and ceric ammonium nitrate carry out reactions to obtain the spiro-2-azidoindoline. In the formula (I), (II), (III), and (IV), the R1 represents at least one of hydrogen, a C1-C5 alkyl group, a C1-C5 alkyloxy group, F, Br and Cl; the X represents O or TsN, TsN represents p-toluenesulfonyl; and the R2 represents a C1-C5 alkyl group. The precursor is sodium azide or trimethylsilyl azide. The mole ratio of indoles represented by the formula (I) or (II) to precursor to ceric ammonium nitrate is 1:(1-3):(2-6). According to the preparation method, azide is introduced into an organic molecule through a simple method, namely, indoles with different structures are tank as the raw materials, and under the effects of a precursor that can provide azido groups and ceric ammonium nitrate, spiro-2-azidoindoline is successfully prepared. The provided method has the advantages of easily prepared raw materials, mild reaction conditions, and convenient operation, and the yield can reach 94%.
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Paragraph 0045; 0046; 0047
(2016/10/10)
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- Chemoselective N-acylation of indoles and oxazolidinones with carbonylazoles
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Unique reactivity: In the presence of more reactive amine and alcohol functional groups and of carboxylic acids, the chemoselective N-acylation of indoles (see scheme) and oxazolidinones is achieved by taking advantage of the unique reactivity of carbonylazole acylating agents with catalytic amounts of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). Copyright
- Heller, Stephen T.,Schultz, Erica E.,Sarpong, Richmond
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supporting information; experimental part
p. 8304 - 8308
(2012/09/08)
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- An efficient method for the preparation of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC)
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An efficient method for the synthesis of mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate using ethyl-1-imidazole carbamate (EImC) has been described. Using this method many sterically hindered and highly substituted mono α-aryl derivatives of diethyl malonate and ethyl cyanoacetate were synthesized in high yield.
- Behera, Manoranjan,Venkat Ragavan,Sambaiah,Erugu, Balaiah,Rama Krishna Reddy,Mukkanti,Yennam, Satyanarayana
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body text
p. 1060 - 1062
(2012/03/26)
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- CDI-mediated monoacylation of symmetrical diamines and selective acylation of primary amines of unsymmetrical diamines
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A highly efficient and green protocol for monoacylation of symmetrical diamines and chemoselective acylation of primary amines of unsymmetrical diamines has been developed.
- Verma, Sanjeev K.,Ghorpade, Ramarao,Pratap, Ajay,Kaushik
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experimental part
p. 326 - 329
(2012/04/10)
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- Solvent free, N,N'-carbonyldiimidazole (CDI) mediated amidation
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The method involves CDI mediated amidation under solvent-free conditions. The protocol is green, simple, and scalable and has broad structural applicability. The protocol has also been used for BOC protection of amine. The protocol has reduced the time for CDI mediated amidation from 2-4 h to 5-10 min without the use of any dry organic solvent and nitrogen atmosphere.
- Verma, Sanjeev K.,Ghorpade, Ramarao,Pratap, Ajay,Kaushik
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experimental part
p. 2373 - 2376
(2012/05/31)
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- On the reactivity of imidazole carbamates and ureas and their use as esterification and amidation reagents
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The optimization, substrate scope, and mechanism of esterification and amidation of carboxylic acids mediated by imidazole-based reagents are discussed. The innate reactivity of carbonylimidazole reagents with a range of nucleophiles is also explored. New reagents developed for the synthesis of α,β-unsaturated esters are described, as are reagents for the preparation of tertiary amides directly from carboxylic acids.
- Heller, Stephen T.,Sarpong, Richmond
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body text
p. 8851 - 8859
(2011/12/02)
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- Chemoselective esterification and amidation of carboxylic acids with imidazole carbamates and ureas
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Imidazole carbamates and ureas were found to be chemoselective esterification and amidation reagents. A wide variety of carboxylic acids were converted to their ester or amide analogues by a simple synthetic procedure in high yields.
- Heller, Stephen T.,Sarpong, Richmond
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supporting information; experimental part
p. 4572 - 4575
(2010/12/25)
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- A simple and efficient procedure for the synthesis of an alendronate- oligonucleotide conjugate via a carbamate linker
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In order to combine the biological properties of oligonucleotides, a synthetic chemical modelized reaction was performed and the procedure then applied to the preparation of an alendronate-deoxyoligonucleotide conjugate through a carbamate linker.
- Lecouvey,Dufau,El Manouni,Leroux
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p. 2109 - 2120
(2007/10/03)
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- ACYCLIC CARBONATES OF β-CYCLODEXTRIN
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The synthesis of acyclic carbonates of β-cyclodextrin obtained from the reaction of alkyloxycarbonylimidazole with β-cyclodextrin, is described.The reaction gave a mixture of linear carbonates which were characterized via TLC, HPLC, 13C NMR and FT-IR.No cyclic carbonates have been detected.The products obtained are low-melting, surface active, easily soluble in water and show good inclusion properties.Their average degree of substitution varies depending on the reaction conditions used.
- Trotta, Francesco,Moraglio, Giovanni,Marzona, Mario,Maritano, Silvana
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p. 559 - 562
(2007/10/02)
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- Imidazole compound and process for preparing the same
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An imidazole compound is disclosed, which is represented by formula (I): STR1 wherein: X represents a --COOT group, in which T represents a hydrogen atom, an alkyl group, a benzyl group, or a phenyl group; or a --CONH2 group, Y represents a hydrogen atom, a chlorine atom, or a bromine atom, Z represents an alkyl group containing from 2 to 6 carbon atoms, which may be substituted with one or more halogen atoms; or a phenyl group which may be substituted with one or more halogen atoms or alkyl groups, and Q represents a hydrogen atom; an --SO2 R1 group, in which R1 represents an alkyl group, a dialkylamino group, or a phenyl group which may be substituted with one or more alkyl groups; or a --CH(R2)(R3) group, in which R2 represents a hydrogen atom, a methyl group, or an alkoxy group, and R3 represents an alkoxy group, an --OCH2 CH2 Si (CH3) group, or a phenyl group which may be substituted with one or more alkyl groups or alkoxy groups, provided that when Y and Q each represents a hydrogen atom and Z represents a phenyl group, X represents a group other than a --COOH-phenyl group, and a --CONH2 group; and that when Y and Q each represents a hydrogen atom and Z represents an n--C5 H11 group, X represents a group other than a --COOH group and a --COOC2 H5 group. Processes for preparing imidazole compounds are also disclosed. The imidazole compounds are useful as an intermediate for production of biocides for controlling harmful organisms in the agricultural and horticultural areas, or medical and pharmaceutical fungicides.
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- A VERSATILE METHOD FOR PREPARATION OF O-ALKYLPEROXICARBONIC ACIDS: EPOXIDATION WITH ALKYLOXYCARBONYLIMIDAZOLES AND HYDROGEN PEROXIDE
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A variety of O-alkylperoxycarbonic acids (2) were conveniently prepared in situ by utilizing alkyloxycarbonylimidazoles (1) as their precursors.Epoxidation of alkenes with such peroxy-acids was studied and their reactivities were compared with those of peroxycarboxylic acids.
- Tsunokawa, Youko,Iwasaki, Shigeo,Okuda, Shigenobu
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p. 2113 - 2116
(2007/10/02)
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- α-Nitro Ketones and Esters from Acylimidazoles
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The anion of 2-(2-nitroethyl)-1,3-dioxolane (4), prepared from the corresponding 2-bromo compound (3), undergoes condensation with acylimidazoles to give the 3-nitro-4-oxobutanal acetals (9), which can serve as valuable polyfunctional intermediates.Condensation with 1-(methoxyoxalyl)imidazole gives the tetrafunctionalized methyl 4-(1,3-dioxolan-2-yl)-3-nitro-2-oxobutanoate (13), which, however, decomposed on attempted deprotection of the ester function.The syntheses in excellent yields of simple α-nitro ketones and α-nitro esters from acylimidazoles and nitroethane and 2-nitropropane are also described.
- Crumbie, Robyn L.,Nimitz, Jonathan S.,Mosher, Harry S.
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p. 4040 - 4045
(2007/10/02)
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