- The Photolysis of 2-Phenyltetrazole
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The photolysis of 2-phenyltetrazole (1) in benzene yields phenylcyanamide (27percent) and the phenylhydrazone of o-aminobenzoyl cyanide (53percent) whose structure was determined by X-ray crystal structure analysis.
- Koga, Nobuko,Koga, Gen,Springer, James P.,Arison, Byron H.,Anselme, Jean-Pierre
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Read Online
- 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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- Synthesis of nitriles via the iodine-mediated dehydrosulfurization of thioamides
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A simple general method for the synthesis of nitriles using the inexpensive and easy to handle iodine (I2) is described herein. The reaction of thioamides with I2 in the presence of triethylamine at room temperature under aerobic conditions afforded various nitriles bearing aryl, vinyl, and alkyl groups in good-to-excellent yields. This method was also effective for conversion from thioureas to cyanamides.
- Murata, Yuki,Iwasa, Hitomi,Matsumura, Mio,Yasuike, Shuji
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p. 679 - 681
(2020/07/30)
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- 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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- 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)
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- Cyanide-Free Synthesis of Air Stable N-Substituted Li and K Cyanamide Salts from Tetrazoles. Applications toward the Synthesis of Primary and Secondary Cyanamides as Precursors to Amidines
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A practical two-step synthesis of N,N′-disubstituted cyanamides consists in the low-temperature metalation of N-substituted 5H-tetrazoles that undergo spontaneous cycloreversion at 0 °C releasing dinitrogen, and forming N-metalated cyanamides that can be reacted in situ with a variety of electrophiles. Remarkably, the N-substituted Li and K cyanamides are air stable white solids at room temperature. Addition of lithium organometallics to the N,N′-disubstituted cyanamides provides a new method for accessing N,N′-disubstituted amidines.
- Duchamp, Edouard,Hanessian, Stephen
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p. 8487 - 8491
(2020/11/12)
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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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supporting information
p. 7684 - 7688
(2019/08/30)
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- Photolysis and Pyrolysis of Phenyltetrazoles: Formation of Phenylcarbodiimide, N-Phenylnitrile Imine, Phenylnitrene, Indazole, and Fulvenallene
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Photolysis of 1-phenyltetrazole 2b at either 193 or 266 nm in a Ne matrix as well as flash vacuum pyrolysis (FVP) of the same compound with isolation of the products in Ne matrix generate phenylcarbodiimide PhN=C=NH 6 very efficiently as the principal product in an almost pure state. Minor amounts of phenyl azide 8 and 1-azacyclohepta-1,2,4,6-tetraene 10, the product of ring expansion of phenylnitrene, are also formed, and the amounts of both substances increase as a function of photolysis time. The photolysis of 2-phenyltetrazole 1b in a Ne matrix at 266 nm for 0.5 min generates the allenic N-phenylnitrile imine PhN=N(+)=CH(–) 3b, absorbing strongly and cleanly at 2021 cm–1 in the IR spectrum. At longer photolysis times peaks ascribed to phenyl azide, phenylnitrene, 1-azacycloheptatetraene, and phenylcarbodiimide 6 become prominent. FVP of 2-phenyltetrazole yields indazole 15 as the major product together with a small amount of phenylcarbodiimide 6. Indazole formation is ascribed to cyclization of the nitrile imine in the ground state. It is not formed on FVP of 1-phenyltetrazole in agreement with the computational result that the thermodynamically most favourable path for rearrangement of the putative N-phenylimidoylnitrene 5b yields phenylcarbodiimide 6 rather than phenylnitrile imine 3b. Further pyrolysis of indazole affords a minor yield of fulvenallene 18.
- Zhao, Xiaofang,Liu, Qian,Feng, Ruijuan,Zeng, Xiaoqing,Wentrup, Curt
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p. 6945 - 6950
(2019/11/20)
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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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- 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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- 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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p. 13788 - 13791
(2018/09/14)
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- Synthesis and Reactivity of N-Allenyl Cyanamides
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N-Allenyl cyanamides have been accessed via a one-pot deoxycyanamidation-isomerization approach using propargyl alcohol and N-cyano-N-phenyl-p-methylbenzenesulfonamide. The utility of this novel class of allenamide was explored through derivatization, with hydroarylation, hydroamination, and cycloaddition protocols employed to access an array of cyanamide products that would be challenging to access using existing methods.
- Ayres, James N.,Williams, Matthew T.J.,Tizzard, Graham J.,Coles, Simon J.,Ling, Kenneth B.,Morrill, Louis C.
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supporting information
p. 5282 - 5285
(2018/09/13)
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- Development of S-Substituted Thioisothioureas as Efficient Hydropersulfide Precursors
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Because of their inherent instability, hydropersulfides (RSSH) must be generated in situ using precursors, but very few physiologically useful RSSH precursors have been developed to date. In this work, we report the design, synthesis, and evaluation of novel S-substituted thiosiothioureas as RSSH precursors. These water-soluble precursors show efficient and controllable release of RSSH under physiological conditions.
- Khodade, Vinayak S.,Toscano, John P.
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p. 17333 - 17337
(2019/01/04)
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- Synthesis of 1,2,4-Triazol-3-imines via Selective Stepwise Cycloaddition of Nitrile Imines with Organo-cyanamides
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A convenient method for the synthesis of 1,2,4-triazol-3-imines through a selective, formal, 1,3-dipolar cycloaddition of organo-cyanamide ions with nitrile imine dipoles is reported. Hydrolysis of the 1,2,4-triazol-3-imines yields the corresponding 1,2,4-triazol-5-ones. A stepwise mechanism, supported by DFT calculations, is invoked to explain the reaction selectivity.
- Sharma, Pallavi,Bhat, Shreesha V.,Prabhath, M. R. Ranga,Molino, Andrew,Nauha, Elisa,Wilson, David J. D.,Moses, John E.
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supporting information
p. 4263 - 4266
(2018/07/29)
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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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p. 918 - 922
(2018/02/03)
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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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- A novel one-pot synthesis of isothiocyanates and cyanamides from dithiocarbamate salts using environmentally benign reagent tetrapropylammonium tribromide
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A highly efficient and simple protocol for the synthesis of isothiocyanates and cyanamides from their respective amines in the presence of a mild, efficient, and non-toxic reagent tetrapropylammonium tribromide is described. High environmental acceptability of the reagents, cost effectiveness and high yields are the important attributes of this methodology.
- Kuotsu, Neivotsonuo Bernadette,Jamir, Latonglila,Phucho, Tovishe,Sinha, Upasana Bora
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p. 832 - 841
(2018/01/17)
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- Deoxycyanamidation of Alcohols with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)
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The first one-pot deoxycyanamidation of alcohols has been developed using N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) as both a sulfonyl transfer reagent and a cyanamide source, accessing a diverse range of tertiary cyanamides in excellent isolated yields. This approach exploits the underdeveloped desulfonylative (N-S bond cleavage) reactivity pathway of NCTS, which is more commonly employed for electrophilic C- and N-cyanation processes.
- Ayres, James N.,Ashford, Matthew W.,St?ckl, Yannick,Prudhomme, Vassili,Ling, Kenneth B.,Platts, James A.,Morrill, Louis C.
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supporting information
p. 3835 - 3838
(2017/07/26)
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- Copper-Catalyzed Three-Component Tandem Cyclization for One-Pot Synthesis of 1,4-Benzothiazines
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A copper-catalyzed three-component tandem reaction has been developed for the convenient and practical synthesis of 1,4-benzothiazines. A variety of terminal alkynes and 2-iodo/bromophenyl isothiocyanates underwent this one-pot cyclization with aqueous ammonia to afford 1,4-benzothiazines in moderate to good yields.
- Chu, Jing-Jing,Hu, Bo-Lun,Liao, Zhi-Yong,Zhang, Xing-Guo
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p. 8647 - 8652
(2016/09/28)
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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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- Facile Gold-Catalyzed Heterocyclization of Terminal Alkynes and Cyanamides Leading to Substituted 2-Amino-1,3-Oxazoles
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Facile gold-catalyzed heterocyclization based upon intermolecular trapping of the generated α-oxo gold carbenes with various cyanamides R2R3NCN (R2/R3 = Alk/Alk, -(CH2)2O(CH2)2-, Ar/Ar, Ar/H) has been developed. In most cases, 2-amino-1,3-oxazoles functionalized at the nitrogen atom as well as at the fifth position of the heterocyclic ring (12 examples) were isolated in good to moderate yields.
- Rassadin, Valentin A.,Boyarskiy, Vadim P.,Kukushkin
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supporting information
p. 3502 - 3505
(2015/07/28)
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- Cobalt-Catalyzed Electrophilic Cyanation of Arylzinc Halides with N-Cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS)
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The cobalt-catalyzed cross-coupling of organozinc bromides with N-cyano-N-phenyl-p-methylbenzenesulfonamide (NCTS) is described. The same cobalt catalyst, cobalt(II) bromide, was used for both the synthesis of the organozinc species and the cross-coupling reaction. However in this case, a catalytic amount of zinc dust is necessary in the second step to release the low-valent cobalt. Under these mild conditions, moderate to excellent yields of different benzonitriles were obtained.
- Cai, Yingxiao,Qian, Xin,Rrat, Alice,Auffrant, Audrey,Gosmini, Corinne
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supporting information
p. 3419 - 3423
(2016/01/25)
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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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supporting information
p. 1823 - 1826
(2015/08/06)
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- Synthesis, structure activity relationship, radiolabeling and preclinical evaluation of high affinity ligands for the ion channel of the N-methyl-d-aspartate receptor as potential imaging probes for positron emission tomography
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The N-methyl-d-aspartate receptor (NMDAr) is involved in many neurological and psychiatric disorders including Alzheimer's disease and schizophrenia. Currently, it is not possible to assess NMDAr availability in vivo. The purpose of this study was to develop a positron emission tomography (PET) ligand for the NMDAr ion channel. A series of di- and tri-N-substituted diarylguanidines was synthesized. In addition, in vitro binding affinity for the NMDAr ion channel in rat forebrain membrane fractions was assessed. Compounds 10, 11 and 32 were radiolabeled with either carbon-11 or fluorine-18. Ligands [11C]10 and [18F]32 were evaluated ex vivo in B6C3 mice. Biodistribution studies showed higher uptake of [11C]10 and [18F]32 in forebrain regions compared with cerebellum. In addition, for [11C]10 54% and for [18F]32 70% of activity in the brain at 60 min was due to intact tracer. Pre-treatment with MK-801 (0.6 mg·kg-1, ip) slightly decreased uptake in NMDAr-specific regions for [18F]32, but not for [11C]10. As such [18F]32 has the best characteristics as a PET tracer for the ion channel of the NMDAr.
- Klein, Pieter J.,Christiaans, Johannes A.M.,Metaxas, Athanasios,Schuit, Robert C.,Lammertsma, Adriaan A.,Van Berckel, Bart N.M.,Windhorst, Albert D.
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p. 1189 - 1206
(2015/03/04)
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- Cleavage of C-N bonds in guanidine derivatives and its relevance to efficient C-N bonds formation
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Efficient nonenzymatic decomposition of guanidine derivatives with high structural and functional diversity into anilide products is achieved in the presence of PdII/Cu(II) carboxylates/CO, relying on a dual C-N bonds cleavage strategy. In this decomposition process, the cooperative action of PdII species, Cu(II) carboxylates, and CO provides not only the N-acylating agents but also an initiator to trigger this C-N bonds cleavage sequence. The current results indicate that PdII/Cu(II) carboxylates/CO system provides a convenient and practical method for highly selective cleavage of unreactive C-N single bonds.
- Chang, Denghu,Zhu, Dan,Zou, Peng,Shi, Lei
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p. 1684 - 1693
(2015/03/30)
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- Synthesis of cyanamides from isoselenocyanates promoted by recyclable ionic liquid-supported (diacetoxyiodo)benzene
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One-pot synthesis of cyanamides from isoselenocyanates through deselenisation promoted by ionic liquid-supported hypervalent iodine(III) reagent 1-(4-diacetoxyiodobenzyl)-3-methylimidazolium tetrafluoroborate [dibmim BF4 was developed. This approach provided a simple, mild and environmentally benign way to construct cyanamides in good yields. Moreover, powder Se and dibmim + BF4 could be easily recycled. It was the first example of [dibmim] + [BF4- to be used as a deselenising agent.
- Li, Xue,Huang, Yingyi,Gan, Bin,Mi, Zhisheng,Xie, Yuanyuan
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p. 631 - 634
(2016/01/25)
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- Bond-shift isomers: The co-existence of allenic and propargylic phenylnitrile imines
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We discovered a 1,3-dipolar species co-existing in two different structures. Photolysis of matrix-isolated 5-phenyltetrazole generates two forms of phenylnitrile imine: propargylic and allenic. They are not resonance structures but correspond to different energy minima, representing bond-shift isomers. These distinct species were characterized spectroscopically and confirmed by calculations up to the CASSCF(14,12) theory level.
- Nunes, Cláudio M.,Reva, Igor,Fausto, Rui,Bégué, Didier,Wentrup, Curt
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supporting information
p. 14712 - 14715
(2015/10/05)
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- Efficient iron(III) porphyrins-catalyzed oxidation of guanidoximes to cyanamides in ionic liquids
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Water soluble iron(III) porphyrins immobilized in imidazolium ionic liquids serve as an effective catalyst for the H2O2 mediated oxidation of guanidoximes to selectively give corresponding cyanamides in good yields. The use of ionic liquid with non-coordinating counter anion PF6 affords the product in high yield by facilitating the formation of anionic iron peroxo intermediate. [Figure not available: see fulltext.]
- Kumari, Pratibha,Nagpal, Ritika,Chauhan, Prashant,Yatindranath, Vinith,Chauhan, Shive M. S.
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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
-
supporting information
p. 892 - 895
(2014/03/21)
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- 2-KETO AMIDE DERIVATIVES AS HIV ATTACHMENT INHIBITORS
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Compounds of Formula I, including pharmaceutically acceptable salts thereof: I useful as HIV attachment inhibitors.
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Page/Page column 67
(2014/10/15)
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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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- 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
-
supporting information
p. 314 - 317
(2014/01/23)
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- Synthesis of amides through an oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions
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A simple, inexpensive and efficient one-pot synthesis of amides was achieved in good yields via the direct oxidative amidation of tetrazoles with aldehydes under transition-metal-free conditions.
- Du, Juan,Luo, Kai,Zhang, Xiuli
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p. 54539 - 54546
(2015/01/09)
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- Aromatic Bis-N -hydroxyguanidinium Derivatives: Synthesis, Biophysical, and Biochemical Evaluations
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In this paper we report the synthesis of a new family of hydroxyguanidinium aromatic derivatives (4a-g) as potential minor groove binders and cytotoxic agents. Their DNA affinity was evaluated by thermal denaturation experiments using salmon sperm DNA. The antiproliferative effects of derivatives 4a, 4d, and 4f were evaluated in human promyelocytic HL-60, breast carcinoma MCF-7, and neuroblastoma Kelly cell lines using the AlamarBlue viability assay, and IC 50 values were obtained. All three compounds were active in the HL-60 cell line. In particular, 4b exhibits antiproliferative effects in all three cell lines while 4d reduced HL-60 and Kelly viability. Both 4b and 4d produced considerable antiproliferative activity in the Kelly cell line. Derivative 4d was chosen for further cell cycle and apoptosis studies using flow cytometric analysis of cellular DNA content.
- Kahved?i?, Amila,Nathwani, Seema-Maria,Zisterer, Daniela M.,Rozas, Isabel
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supporting information
p. 451 - 459
(2013/04/23)
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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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- COMPOUNDS AND COMPOSITIONS AS C-KIT KINASE INHIBITORS
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The invention provides compounds and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of c-kit or c-kit and PDGFR (PDGFRα, PDGFRβ) kinases.
- -
-
Paragraph 0407; 0408
(2013/03/26)
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- COMPOUNDS AND COMPOSITIONS AS C-KIT KINASE INHIBITORS
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The invention provides compounds and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of c-kit or c-kit and PDGFR (PDGFRα, PDGFRβ) kinases.
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Page/Page column 83-84
(2013/03/28)
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- COMPOUNDS AND COMPOSITIONS AS C-KIT KINASE INHIBITORS
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The invention provides compounds of formulae (I) and (II) and pharmaceutical compositions thereof, which are useful as protein kinase inhibitors, as well as methods for using such compounds to treat, ameliorate or prevent a condition associated with abnormal or deregulated kinase activity. In some embodiments, the invention provides methods for using such compounds to treat, ameliorate or prevent diseases or disorders that involve abnormal activation of c-kit or c-kit and PDGFR (PDGFRcalpha PDGFRbeta) kinases
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Page/Page column 90; 91
(2013/03/28)
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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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- Environmentally benign one-pot synthesis of cyanamides from dithiocarbamates using I2 and H2O2
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An environmentally benign reaction is devised for the synthesis of cyanamides from dithiocarbamate salts using iodine and H2O 2. Taylor & Francis Group, LLC.
- Jamir, Latonglila,Sinha, Upasana Bora,Nath, Jayashree,Patel, Bhisma K.
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experimental part
p. 951 - 958
(2012/02/01)
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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)
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- 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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- Nitrile imines: Matrix isolation, IR spectra, structures, and rearrangement to carbodiimides
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The structures and reactivities of nitrile imines are subjects of continuing debate. Several nitrile imines were generated photochemically or thermally and investigated by IR spectroscopy in Ar matrices at cryogenic temperatures (Ph-CNN-H 6, Ph-CNN-CH317, Ph-CNN-SiMe323, Ph-CNN-Ph 29, Ph3C-CNN-CPh334, and the boryl-CNN-boryl derivative 39). The effect of substituents on the structures and IR absorptions of nitrile imines was investigated computationally at the B3LYP/6-31G level. IR spectra were analyzed in terms of calculated anharmonic vibrational spectra and were generally in very good agreement with the calculated spectra. Infrared spectra were found to reflect the structures of nitrile imines accurately. Nitrile imines with IR absorptions above 2200 cm -1 have essentially propargylic structures, possessing a CN triple bond (typically PhCNNSiMe323, PhCNNPh 29, and boryl-CNN-boryl 39). Nitrile imines with IR absorptions below ca. 2200 cm-1 are more likely to be allenic (e.g., HCNNH 1, PhCNNH 6, HCNNPh 43, PhCNNCH317, and Ph3C-CNN-CPh334). All nitrile imines isomerize to the corresponding carbodiimides both thermally and photochemically. Monosubstituted carbodiimides isomerize thermally to the corresponding cyanamides (e.g., Ph-N=C=N-H 5 Ph-NH-CN 8), which are therefore the thermal end products for nitrile imines of the types RCNNH and HCNNR. This tautomerization is reversible under flash vacuum thermolysis conditions.
- Begue, Didier,Qiao, Greg Guanghua,Wentrup, Curt
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scheme or table
p. 5339 - 5350
(2012/05/20)
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- Bromineless bromine as an efficient desulfurizing agent for the preparation of cyanamides and 2-aminothiazoles from dithiocarbamate salts
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In a one-pot procedure, bromineless brominating reagent 1,1'-(ethane-1,2-diyl)dipyridinium bistribromide (EDPBT) has been used as a desulfurizing agent in the preparation of organic cyanamides and substituted thiazoles starting from dithiocarbamic acid salts. In this approach, alkyl/aryl isothiocyantes were first obtained by the desulfurization of dithiocarbamic acid salts with EDPBT. The in situ-generated isothiocyanates reacts with an aqueous ammonia, forming alkyl or aryl thioureas, which on subsequent oxidative desulfurization with EDPBT led to the formation of corresponding cyanamides in good yields. Alternatively, an efficient one-pot synthesis of substituted thiazoles has been achieved by the condensation of the in situ-generated 1-aryl thioureas with the in situ-generated -bromoketones from ketones, again using EDPBT. The reagent EDPBT can be easily prepared from the readily available reagents. Desulfurizing ability dominates over its brominating ability for substrates amenable to bromination.
- Yella, Ramesh,Kavala, Veerababurao,Patel, Bhisma K.
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experimental part
p. 792 - 805
(2011/04/22)
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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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- Direct C-H arylation and alkenylation of 1-substituted tetrazoles: Phosphine as stabilizing factor
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(Chemical Equation Presented) Direct arylation and alkenylation of 1-substituted tetrazoles was achieved via Pd catalysis in the presence of CuI and Cs2CO3. Unlike the related reactions of imidazoles and purines, phosphine ligand was
- Spulak, Marcel,Lubojacky, Richard,Senel, Petr,Kunes, Jiri,Pour, Milan
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scheme or table
p. 241 - 244
(2010/04/06)
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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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- A one-pot preparation of cyanamide from dithiocarbamate using molecular iodine
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An efficient one-pot method for the synthesis of cyanamides from dithiocarbamate salts via a double desulfurization strategy using molecular iodine is disclosed. Dithiocarbamates, by the action of iodine yield isothiocyanates in situ, which on treatment with aqueous NH3 give thioureas. The thioureas so generated undergo further oxidative desulfurization with I2 giving corresponding cyanamides in good yields. Environmental benignity, cost effectiveness and high yields are the important attributes of this one pot procedure. The Royal Society of Chemistry 2009.
- Nath, Jayashree,Patel, Bhisma K.,Jamir, Latonglila,Sinha, Upasana Bora,Satyanarayana
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experimental part
p. 1503 - 1506
(2010/05/18)
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- Alkoxy isothiocyanates as intermediates in the flash vacuum pyrolysis of alkoxythioureas
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Methoxy isothiocyanate MeONCS 2b was detected by matrix isolation IR spectroscopy following flash vacuum pyrolysis (FVP) of N-methoxythioureas, N-tert-butyl-N′-methoxythiourea 1d being the best precursor. Isothiocyanates 3, amines, and aldehydes are also
- Pedersen, Carl Th.,Jensen, Frank,Flammang, Robert
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experimental part
p. 69 - 74
(2009/07/18)
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