- Iron-mediated desulphurization approach: synthesis of cyanamides and their conversions
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The iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology. All the reactions are rapid, facile, and accomplished at room temperature. A variety of substrates readily underwent the optimized reaction conditions to provide their respective target products in good to excellent yields. Furthermore, we have confirmed that no other by-products could be identified during our experimental reaction process. Graphical abstract: Iron-mediated efficient multi-component method has been demonstrated for the synthesis of substituted cyanamides from isothiocyanates under mild reaction conditions. Subsequent nucleophilic addition and desulfurization are involved in this proposed synthetic methodology.[Figure not available: see fulltext.].
- Nannapaneni, Madhavi,Pendem, Venkata Bhavanarushi,Tamminana, Ramana
-
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- On Reactions of 5-Imino-N,4-diaryl-4,5-dihydro-1,2,4-thiadiazol-3-amines with Phenylethynyl Sulfones
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Abstract: N-Arylthioureas were reacted with hydrogen peroxide to synthesize 5-imino-N,4-diaryl-4,5-dihydro-1,2,4-thiadiazol-3-amines (Ar = Ph, p-Tol, 4-BrC6H4). The products undewent 1,3-dipolar cycloaddition to (R-ethynyl)sulfonyl b
- Kostryukov, S. G.,Masterova, Yu. Yu.,Pugacheva, E. Yu.
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p. 219 - 225
(2022/04/19)
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- CF3SO2Na as a Bifunctional Reagent: Electrochemical Trifluoromethylation of Alkenes Accompanied by SO2 Insertion to Access Trifluoromethylated Cyclic N-Sulfonylimines
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An unprecedented electrochemical trifluoromethylation/SO2 insertion/cyclization process has been achieved in an undivided cell in an atom-economic fashion. The protocol relies on tandem cyclization of N-cyanamide alkenes by using Langlois’ reagent as a source of both CF3 and SO2 under direct anodically oxidative conditions, in which two C?C bonds, two C?X bonds (N?S and S?C), and two rings were formed in a single operation. This transformation enabled efficient construction of various trifluoromethylated cyclic N-sulfonylimines from readily accessible materials.
- He, Zeying,Jiao, Lingcong,Li, Zheng,Liao, Wei-Wei,Sun, Yunhai,Wei, Zhonglin
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supporting information
p. 7266 - 7270
(2020/03/23)
-
- SO2F2-Mediated one-pot cascade process for transformation of aldehydes (RCHO) to cyanamides (RNHCN)
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A simple, mild and practical cascade process for the direct conversion of aldehydes to cyanamides was developed featuring a wide substrate scope and great functional group tolerability. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable cyanamides in a pot, atom, and step-economical manner with a green nitrogen source. This protocol will serve as a robust tool for the installation of the cyanamide moiety in various complicated molecules.
- Ding, Chengrong,Ge, Shuting,Wei, Junjie,Zhang, Guofu,Zhao, Yiyong
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p. 17288 - 17292
(2020/05/18)
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- A cascade process for directly converting nitriles (RCN) to cyanamides (RNHCN) via SO2F2-activated Tiemann rearrangement
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A simple, mild and practical process for the direct conversion of nitriles to cyanamides was newly discovered and exhibited a wide substrate scope as well as great functional group-tolerability (36 examples). In this efficient strategy, the in situ generated amidoximes obtained from the reaction of nitriles with hydroxylamine subsequently underwent Tiemann rearrangement, producing the corresponding cyanamides with great isolated yields under SO2F2. Additionally, the control experiments reportedly shed light on the tentative mechanism involved in the formation and elimination of the key intermediate: a sulfonyl ester.
- Zhang, Guofu,Zhao, Yiyong,Ding, Chengrong
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p. 7684 - 7688
(2019/08/30)
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- Selective Gold-Catalysed Synthesis of Cyanamides and 1-Substituted 1H-Tetrazol-5-Amines from Isocyanides
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The newly discovered gold-catalysed reaction of isocyanides with hydrazoic acid generated in situ from trimethylsilyl azide and methanol (or, alternatively, from NaN3/AcOH) produces either cyanamides or 1-substituted 1H-tetrazol-5-amines, depending on the amount of available HN3. The reaction proceeds selectively and in generally high yields of either product, thus providing a particularly convenient access to a wide range of substituted 1H-tetrazol-5-amines that are rather difficult to access otherwise.
- ?koch, Karel,Císa?ová, Ivana,?těpni?ka, Petr
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supporting information
p. 13788 - 13791
(2018/09/14)
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- Cobalt-promoted one-pot reaction of isothiocyanates toward the synthesis of aryl/alkylcyanamides and substituted tetrazoles
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[Figure not available: see fulltext.] The synthesis of cyanamides and tetrazoles from isothiocyanates through tandem reaction using cobalt catalyst has been demonstrated. In the case of tetrazole preparation, the reaction involved addition/desulfurization/nucleophilic addition/electrocyclization, whereas aromatic cyanamides were constructed from isothiocyanates through addition/desulfurization. Cheap cobalt sulfate was used for the synthesis of various cyanamides and tetrazoles. In addition, cobalt catalyst was found to be desulfurization reagent that has not been previously reported. The final products have been obtained from starting precursors in good to high yield.
- Seelam, Mohan,Kammela, Prasada Rao,Shaikh, Bajivali,Tamminana, Ramana,Bogiri, Sujatha
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p. 535 - 544
(2018/07/05)
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- Fe3O4@SiO2 nanoparticle supported ionic liquid for green synthesis of antibacterially active 1-carbamoyl-1-phenylureas in water
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In the present work, we have designed a novel, heterogeneous and recyclable magnetic Br?nsted acidic ionic liquid based on 5-phenyl-1H-tetrazole. The {Fe3O4@SiO2@CH2)35-phenyl-1H-tetrazole-SO3H/Cl} ([FSTet-SO3H]Cl) was prepared via the immobilization of 5-phenyl-1H-tetrazole-bonded sulfonic acid onto the surface of silica-coated magnetic nanoparticles using 3-chloropropyltriethoxysilane as a linker. The catalyst was characterized by XRD, TEM, FESEM, EDS, TG-DTA, and FT-IR. The ability and high activity of this catalyst were demonstrated in the synthesis of 1-carbamoyl-1-phenylureas with good to excellent yields via a new, simple and one-pot procedure in aqueous media under reflux conditions. This procedure has advantages such as high yields, short reaction times, a simple methodology and work-up process, green reaction conditions, high stability, catalytic activity, and easy preparation, separation and reusability of the catalyst. The synthesis of these compounds was confirmed by FT-IR, 1H NMR, 13C NMR and CHN. In addition, we investigated the biological properties of the 1-carbamoyl-1-phenylureas as newly synthesized compounds. The described catalyst could be easily separated from the reaction mixture by additional magnetic force and reused several times without a remarkable loss of its catalytic activity and any considerable changes in the product yield and the reaction time.
- Nasrollahzadeh, Mahmoud,Issaabadi, Zahra,Sajadi, S. Mohammad
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p. 27631 - 27644
(2018/08/16)
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- One-pot three-component tandem reaction: Synthesis of aryl/alkyl cyanamides libraries and their further conversion into tetrazole derivatives
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We have developed methodology for the synthesis of aryl/alkyl cyanamides from amines in one-pot four steps reaction using cheap, readily available and air stable copper source as catalyst under mild reaction conditions. We have also studied the application of cyanamides. In this connection, we could construct aryl tetrazolamine from cyanamides using click reaction.
- Mandapati, Usharani,Mandapati, Pavan,Pinapati, Srinivasarao,Tamminana, Ramana,Rudraraju, Rameshraju
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supporting information
p. 500 - 510
(2018/02/06)
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- The synthesis of aryl cyanamides through C-N cross-coupling
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The methodology for the preparation of aromatic cyanamides has been demonstrated. The present method involves consecutive desulphurization/C-N cross-coupling reaction. Cheap, readily available and air stable cobalt catalyst has been used for this methodology. In addition, the substrate scope has been explored.
- Kondraganti, Lakshmi,Manabolu, Surendra Babu,Dittakavi, Rama Chandran
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p. 629 - 634
(2020/06/26)
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- The synthesis of arylcyanamides: A copper-catalyzed consecutive desulfurization and C-N cross-coupling strategy
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A one pot highly efficient and simple protocol for the construction of aromatic cyanamides from thiourea via desulphurization/C-N cross coupling using a cheap, readily available and air stable copper source as a catalyst has been described. Various iodobenzenes could give their respective C-N cross-coupled products in good to excellent yields under optimized reaction conditions. Further, the substrate scope has been explored.
- Boddapati, S. N. Murthy,Polam, Naresh,Mutchu, Baby Ramana,Bollikolla, Hari Babu
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supporting information
p. 918 - 922
(2018/02/03)
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- A Metal and Base-Free Chemoselective Primary Amination of Boronic Acids Using Cyanamidyl/Arylcyanamidyl Radical as Aminating Species: Synthesis and Mechanistic Studies by Density Functional Theory
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An efficient, metal and base-free, chemoselective synthesis of aryl-, heteroaryl-, and alkyl primary amines from the corresponding boronic acids has been achieved at ambient temperature mediated by [bis(trifluoroacetoxy)iodo]benzene (PIFA) and N-bromosuccinimide (NBS) using cyanamidyl/arylcyanamidyl radicals as the aminating species. The primary amine compounds were initially obtained as their corresponding ammonium trifluoroacetate salts which, on treatment with aq NaOH, provide the free amines. Finally, the primary amines were isolated through column chromatography over silica-gel using hexane-EtOAc solvent system as the eluent. The reactions are sufficiently fast, completing within 1 h. Quantum chemical calculations in combination with experimental observations validate that the ipso amination of substituted boronic acids involves the formation of cyanamidyl/arylcyanamidyl radical, followed by regiospecific interaction of its nitrile-N center with boron atom of the boronic acids, leading to chemoselective primary amination.
- Chatterjee, Nachiketa,Arfeen, Minhajul,Bharatam, Prasad V.,Goswami, Avijit
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p. 5120 - 5127
(2016/07/06)
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- One-Pot Synthesis of N-Monosubstituted Ureas from Nitriles via Tiemann Rearrangement
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Amidoximes, obtained from the reaction of nitriles with hydroxylamine, underwent Tiemann rearrangement in the presence of benzenesulfonyl chlorides (TsCl or o-NsCl) to form the N-substituted cyanamides. Subsequently, acidic hydrolysis of the cyanamides afforded the corresponding N-monosubstituted ureas. The synthesis of N-monosubstituted ureas from nitriles was accomplished by three steps in one pot, which provides a direct access to versatile N-monosubstituted urea derivatives from a wide variety of nitriles.
- Wang, Chien-Hong,Hsieh, Tsung-Han,Lin, Chia-Chi,Yeh, Wen-Hsiung,Lin, Chih-An,Chien, Tun-Cheng
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p. 1823 - 1826
(2015/08/06)
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- Aminocyanation by the addition of N-CN bonds to arynes: Chemoselective synthesis of 1,2-bifunctional aminobenzonitriles
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An efficient aminocyanation by the direct addition of aryl cyanamides to arynes is described, enabling incorporation of highly useful amino and cyano groups synchronously via cleavage of inert N-CN bonds, affording synthetically useful 1,2-bifunctional aminobenzonitriles. The postsynthetic functionalization of the aminocyanation products allows diverse formation of synthetically important derivatives such as drug molecule Ponstan and fused heterocycles.
- Rao, Bin,Zeng, Xiaoming
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supporting information
p. 314 - 317
(2014/01/23)
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- Copper-catalyzed one-pot synthesis of unsymmetrical arylurea derivatives via tandem reaction of diaryliodonium salts with N -arylcyanamide
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An efficient "one-pot" approach to multiple substituted ureas from N-arylcyanamide and diaryliodonium salts has been presented. The two-step procedure involved the weak base-promoted chemoselective arylation of secondary amines with diaryliodonium and Cu-catalyzed nucleophilic addition of N-arylcyanamide with second diaryliodonium. The diverse unsymmetrical arylureas were obtained in up to 91% yield for 29 examples.
- Li, Pengfei,Cheng, Guolin,Zhang, Hong,Xu, Xianxiang,Gao, Jingyuan,Cui, Xiuling
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p. 8156 - 8162
(2015/03/18)
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- Practical synthesis of N -substituted cyanamides via tiemann rearrangement of amidoximes
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A facile and general synthesis of various N-substituted cyanamides was accomplished by the Tiemann rearrangement of amidoximes with benzenesulfonyl chlorides (TsCl or o-NsCl) and DIPEA.
- Lin, Chia-Chi,Hsieh, Tsung-Han,Liao, Pen-Yuan,Liao, Zhen-Yuan,Chang, Chih-Wei,Shih, Yu-Chiao,Yeh, Wen-Hsiung,Chien, Tun-Cheng
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p. 892 - 895
(2014/03/21)
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- Copper-catalyzed oxidative three-component synthesis of N, N′, N′-trisubstituted guanidines
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A copper-catalyzed three-component synthesis of trisubstituted N-aryl guanidines involving cyanamides, arylboronic acids, and amines has been developed. This operationally simple oxidative process, which is performed in the presence of K2CO3, a catalytic amount of CuCl 2·2H2O, bipyridine, and oxygen (1 atm), allows the rapid assembly of N,N′,N″-trisubstituted aryl guanidines.
- Li, Jihui,Neuville, Luc
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supporting information
p. 6124 - 6127
(2014/01/17)
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- An efficient transformation of ethers to N,N′-disubstituted ureas in a Ritter type reaction
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A simple, mild, and an alternative protocol for the preparation of N,N′-disubstituted ureas from readily available ethers and cyanamides as starting materials is described. The protocol explores the reactivity of ether in a Ritter type reaction with cyanamide in the presence of BF 3·Et2O and resulting in the formation of N,N′-disubstituted urea. Divinyl ether as well as MTBE (methyl tert-butyl ether) can be employed as ether components to afford allyl and tert-butyl ureas respectively.
- Panduranga, Veladi,Basavaprabhu,Sureshbabu, Vommina V.
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p. 975 - 979
(2013/04/10)
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- Iron(III) catalysed synthesis of unsymmetrical di and trisubstituted ureas - A variation of classical Ritter reaction
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An application of the classical Ritter reaction for the synthesis of unsymmetrical di and trisubstituted ureas catalyzed by FeCl3 is described. The protocol is of significant interest in view of the easy availability of precursors, mild reaction conditions employed and interestingly its applicability for the alkylation of alcohols capable of forming stable carbocationic intermediates even to the sterically hindered moieties. The Royal Society of Chemistry 2012.
- Basavaprabhu, Hosamani,Sureshbabu, Vommina V.
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supporting information; experimental part
p. 2528 - 2533
(2012/04/23)
-
- Novel and green protocol for the synthesis of 2-iminohydantoins
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A novel and green protocol for the synthesis of N-1 and C-5 substituted 2-iminohydantoins has been developed. Methyl N-cyano-N-alkyl/aryl-aminoacetate reacts with aqueous ammonia at room temperature in 10-30 min. The developed protocol does not require any work-up for the isolation or purification of the products; simple filtration can lead to the pure products in good to excellent yields.
- Kumar, Vinod,Rana, Hemlata,Kaushik, M. P.
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p. 6423 - 6425,3
(2012/12/12)
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- Copper(I)-catalyzed cascade synthesis of 2-arylsulfanyl-arylcyanamides
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We have developed a ligand-assisted copper(I)-catalyzed two sequential heteroarylation sequence. An intramolecular S-arylation is followed by an intermolecular N-arylation leading to the direct synthesis of N-aryl-2-aminobenzothiazoles. In most cases however, the 2-arylsulfanyl- arylcyanamide was the major product obtained via an intramolecular C-S bond formation, associated with C-S bond breakage, followed by an intermolecular S-arylation. The selectivity of this ligand-assisted reaction is quite different as compared to that of ligand-free reactions and the rates are much faster giving good yields of products. Various cyanamides can be prepared in excellent yields from their corresponding 1-substituted thioureas with or without the assistance of a ligand with a catalytic quantity of copper(I).
- Sahoo, Santosh K.,Jamir, Latonglila,Guin, Srimanta,Patel, Bhisma K.
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experimental part
p. 2538 - 2548
(2010/12/29)
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- Mesoionic carbenes: Reactions of 1, 3-diphenyltetrazol-5-ylidene with electron-deficient alkenes, and synthesis and catalytic activities of the (tetrazol-5-ylidene)rhodium(I) complexes
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The reactions of 1, 3-diphenyltetrazol-5-ylidene, a rare example of mesoionic carbenes, with electron- deficient unsaturated compounds were studied. The carbene reacted with dimethyl 1, 2, 4, 5-tetrazine-3, 6-dicarboxylate to give a 5-tetrazoliomethylide, together with hydrazine derivatives. The reaction with tetracyanoethylene gave another methylide in low yield. On the contrary, the reactions with weaker electrophiles, such as 3, 6-diphenyl-1, 2, 4, 5-tetrazine, fumalonitrile, N-phenylmaleimide, and dimethyl acetylenedicarboxylate, did not give any coupling products, but gave phenylated products and/or Michael addition products via the degradation of the 1, 3-diphenyltetrazole ring. Novel mesoionic mono- and bis(carbene)-rhodium(I) complexes were synthesized and the structures were characterized by X-ray crystallography. Their catalytic activities for the decarbonylative addition reaction of benzoyl chloride to ethynylbenzene were investigated.
- Araki, Shuki,Yokoi, Keisaku,Sato, Ryosuke,Hirashita, Tsunehisa,Setsune, Jun-Ichiro
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experimental part
p. 164 - 171
(2009/07/17)
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- An efficient synthesis of cyanamide from amine promoted by a hypervalent iodine(III) reagent
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In a one-pot strategy we have achieved an efficient method for the synthesis of organic cyanamides starting from dithiocarbamic acid salts/amines. In this strategy the in situ generated alkyl or aryl isothiocyanates, obtained by the desulfurization of dithiocarbamic acid salts with diacetoxyiodobenzene (DIB) react with aqueous ammonia forming alkyl or aryl thiourea which on subsequent oxidative desulfurization with DIB led to the formation of corresponding cyanamide in good yields. Mild reaction conditions, shorter reaction time, an environmentally benign protocol, and easy isolation of the desired product make the present methodology a suitable alternative for the preparation of various organic cyanamides.
- Ghosh, Harisadhan,Yella, Ramesh,Ali, Abdur Rezzak,Sahoo, Santosh K.,Patel, Bhisma K.
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experimental part
p. 2407 - 2410
(2009/07/26)
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- An efficient approach for the synthesis of N-1 substituted hydantoins
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An efficient three-step route for the synthesis of N-1 alkyl/aryl- substituted hydantoins was developed from inexpensive commercially available substrates. The reaction of amines with cyanogen bromide takes place to give monoalkyl/aryl cyanamides. This on treatment with methyl bromoacetate in the presence of sodium hydride in tetrahydrofuran affords methyl N-cyano-N-alkyl/arylaminoacetate, which undergoes hydrolysis and cyclization in the presence of 50% H2SO4 to afford N-1 substituted hydantoins in very good-to-excellent yields. Wide varieties of final products having primary, secondary, tertiary, and aryl substituents at the N-1 position were successfully synthesized by this method. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Kumar, Vinod,Kaushik,Mazumdar, Avik
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experimental part
p. 1910 - 1916
(2009/04/04)
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- Electrochemical and peroxidase oxidation study of N'-hydroxyguanidine derivatives as NO donors.
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The electrochemical properties of a series of N-substituted-N'-hydroxyguanidines were studied. Two oxidation potentials of each compound were obtained by cyclic voltammetry. The E(ox1) values were from 0.51 to 0.62V, while the E(ox2) values were from 1.14 to 1.81V in acetonitrile solution. Next, their enzymatic controlled NO release abilities were evaluated. All N'-hydroxyguanidines exhibited efficient NO release abilities under the oxidation by horseradish peroxidase in the presence of H(2)O(2).
- Cai, Tingwei,Xian, Ming,Wang, Peng George
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p. 1507 - 1510
(2007/10/03)
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- Novel substrates for nitric oxide synthases.
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Enzymatic generation of nitric oxide (NO) by nitric oxide synthase (NOS) consists of two oxidation steps. The first step converts L-arginine to N(G)-hydroxy-L-arginine (NOHA), a key intermediate, and the second step converts NOHA to NO and L-citrulline. To fully probe the substrate specificity of the second enzymatic step, an extensive structural screening was carried out using a series of N-alkyl (and N-aryl) substituted-N'-hydroxyguanidines (1-14). Among the eleven N-alkyl-N'-hydroxyguanidines evaluated, N-n-propyl (2), N-iso-propyl (3), N-n-butyl (4), N-s-butyl (5), N-iso-butyl (6), N-pentyl (8) and N-iso-pentyl (9) derivatives were efficiently oxidized by the three isoenzymes of NOS (nNOS, iNOS and eNOS) to generate NO. N-Butyl-N'-hydroxyguanidine (4) was the best substrate for iNOS (K(m)=33 microM) and N-iso-propyl-N'-hydroxyguanidine (3) was the best substrate for nNOS (K(m)=56 microM). When the alkyl substituents were too small (such as ethyl 1) or too large (such as hexyl 10 and cyclohexyl 11), the activity decreased significantly. This suggests that the van der Waals interaction between the alkyl group and the hydrophobic cavity in the NOS active site contributes significantly to the relative reactivity of compounds 3-11. Moreover, five N-aryl-N'-hydroxyguanidines were found to be good substrates for iNOS, but not substrates for eNOS and nNOS. N-phenyl-N'-hydroxyguanidine was the best substrate among them (K(m)=243 microM). This work demonstrates that N-alkyl substituted hydroxyguanidine compounds are novel NOS substrates which 'short-circuit' the first oxidation step of NOS, and N-aryl substituted hydroxyguanidine compounds are isoform selective NOS substrate.
- Xian, Ming,Fujiwara, Noriko,Wen, Zhong,Cai, Tingwei,Kazuma, Satoshi,Janczuk, Adam J,Tang, Xiaoping,Telyatnikov, Vladislav V,Zhang, Yingxin,Chen, Xinchao,Miyamoto, Yasuhide,Taniguchi, Naoyuki,Wang, Peng George
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p. 3049 - 3055
(2007/10/03)
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- Isolation, reactivity and intramolecular trapping of phosphazide intermediates in the Staudinger reaction of tertiary phosphines with azides
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The Staudinger reaction of the N-substituted o-azidobenzamide 1 with triphenylphosphine or diphenylmethylphosphine allows the isolation of the intermediate phosphazides as crystalline solids, which have been characterized by spectroscopic methods. These compounds react in aza Wittig type fashion with isocyanates to give unexpectedly the corresponding 1,2,3- benzotriazinone derivative. Trapping of a Z-phosphazide by intramolecular aza Wittig reaction is reported for the first time. (C) 2000 Elsevier Science Ltd.
- Desamparados Velasco,Molina, Pedro,Fresneda, Pilar M.,Sanz, Miguel A.
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p. 4079 - 4084
(2007/10/03)
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- Quantitative gas-solid reactions with ClCN and BrCN: Synthesis of cyanamides, cyanates, thiocyanates, and their derivatives
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Gas-solid reaction techniques allow quantitative cyanations with ClCN and BrCN. Three primary and four secondary cyanamides, a cyanimide, four cyanates, and four thiocyanates were all prepared as solids in 100% yield from solid anilines, benzimidazoles, imides, phenolates, and thiolates, respectively. Intramolecular solid-state reactions of cyanated o-aminophenol and of cyanated hydrazides gave heterocyclic compounds. When comparable reactions were performed in solution the reported product yields were considerably less than 100% in all cases. The reasons for the success of the environmentally benign solid-state syntheses are discussed in terms of phase rebuilding, phase transformation, and crystal disintegration. Atomic force microscopy (AFM) of selected systems indicates the occurrence of long-range molecular movements which are governed by the crystal packing. This is evident from the obvious correlations between the molecular movements and the known crystal packing data. A new type of geometric surface feature, a rectangular and a rhombic depression which resembles a swimming-pool basin, was found in the cyanation of o-aminophenol and benzohydrazide.
- Kaupp, Gerd,Schmeyers, Jens,Boy, Juergen
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p. 2467 - 2474
(2007/10/03)
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- Synthesis and Biological Activity of Arylformamidine Sulphides
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Several arylformamidine sulphide dihydrochlorides (IIa-f) have been synthesized by the reaction of arylformamidine chlorides with acetylthiocarbamide, and evaluated for their local anaesthetic and antibacterial activities.Only m-tolyl derivative (IId) has been found to be active as local anaesthetic.All the compounds have been found to be inactive against bacteria.
- Pandeya, S. N.,Raj, Man,Singh, B. N.
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p. 229 - 230
(2007/10/02)
-