- Complexation of Halide Anions and Tricarboxylate Anions by Neutral Urea-Derivatized p-tert-Butylcalixarenes
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Two neutral receptors for halide anions and tricarboxylate anions have been synthesized on the basis of p-tert-butylcalixarene, symmetrically functionalized with three butyl(thio)urea groups at the 1,3,5-phenolic positions.The anion complexation has be
- Scheerder, Jurgen,Engbersen, Johan F. J.,Casnati, Alessandro,Ungaro, Rocco,Reinhoudt, David N.
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- Facile synthesis of phthalidyl fused spiro thiohydantoins through silica sulfuric acid induced oxidative rearrangement of ninhydrin adducts of thioureas
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A one-pot three-component sequential synthetic protocol produces structurally and biologically important phthalidyl fused spiro N,N′-disubstituted thiohydantoins from readily available aromatic isothiocyanates, primary amines and ninhydrin. In this three-step synthesis while the initial two steps are catalyst-free, in the final step silica sulfuric acid (SSA) induces an oxidative rearrangement in [3.3.0]-bicyclic 1,2-diol adducts of ninhydrin and thioureas under solvent-free condition to generate the final products spiro-fused thiohydantoins. The adequate acidity of SSA in cooperation with moderate oxidizing property promotes a facile oxidative rearrangement in 1,2-diol intermediates to produce the spiro-fused thiohydantoins with diverse functionalities. Easy recyclability of SSA, good to excellent yield of the products, wider substrate scope, shorter reaction time, solvent-free two steps out of three and high atom economy make this method attractive and practicable.
- Mandal, Subhro,Pramanik, Animesh
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- Synthesis of metronidazole based thiazolidinone analogs as promising antiamoebic agents
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Metronidazole and its derivatives are widely used for the treatment of amoebiasis. However, metronidazole is considered as the standard drug but it has many side effects. The present study describes the synthesis of a series of metronidazole based thiazolidinone analogs via Knoevenagel condensation of 4-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethoxy]benzaldehyde 1 with various thiazolidinone derivatives 2–14 to get the new scaffold (15–27) having better activity and lesser toxicity. Six compounds have shown better efficacy and lesser cytotoxicity than the standard drug metronidazole towards HM1: IMSS strain of Entamoeba histolytica. These compounds may combat the problem of drug resistance and might be effective in identifying potential alternatives for future drug discovery against EhOASS.
- Ansari, Mohammad Fawad,Inam, Afreen,Ahmad, Kamal,Fatima, Shehnaz,Agarwal, Subhash M.,Azam, Amir
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supporting information
(2020/10/12)
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- Synthesis of thioureido peptidomimetics employing alkyl azides and dithiocarbamates
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An unprecedented approach for the assembly of thioureido peptidomimetics is developed employing alkyl azides and dithiocarbamates. Dithiocarbamates react with alkyl azides with the liberation of N2 and elemental sulfur thereby leading to thiourea in a traceless manner. Thioureido peptidomimetics are thus furnished in good yields with no epimerization. This process is mild, free from the use of a base, scalable and step economic. The practicability of this methodology has been highlighted by the synthesis of N,N′-orthogonally protected thioureido peptidomimetics.
- Roopesh Kumar,Panduranga, Veladi,Vishwanatha,Shekharappa,Sureshbabu, Vommina V.
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p. 2258 - 2263
(2018/04/05)
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- Ph3P/I2-mediated synthesis of N,N′,N″-substituted guanidines and 2-iminoimidazolin-4-ones from aryl isothiocyanates
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A convenient one-pot procedure for the synthesis of acyclic and cyclic guanidines mediated by the Ph3P/I2 system is described. Sequential condensation of aryl isothiocyanates with amines followed by dehydrosulfurization and guanylation could lead to both symmetric and unsymmetric N,N′,N″-substituted derivatives. Through a tandem guanylation-cyclization, a series of 2-iminoimidazolin-4-ones could also be prepared in good yields from the reaction of aryl isothiocyanates with amino acid methyl esters.
- Wangngae, Sirilak,Pattarawarapan, Mookda,Phakhodee, Wong
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p. 10331 - 10340
(2018/05/31)
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- Powerful approach to heterocyclic skeletal diversity by sequential three-component reaction of amines, isothiocyanates, and 1,2-diaza-1,3-dienes
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By highly efficient, one-pot, three-component reactions, combining one set of 1,2-diaza-1,3-dienes (DDs), primary amines, and isothiocyanates in a different sequential order of addition, heterocyclic skeletal diversity can be achieved. The key feature dis
- Attanasi, Orazio A.,Bartoccini, Silvia,Favi, Gianfranco,Giorgi, Gianluca,Perrulli, Francesca Romana,Santeusanio, Stefania
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experimental part
p. 1161 - 1167
(2012/03/12)
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- A versatile thiouronium-based solid-phase synthesis of 1,3,5-triazines
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A thiouronium-based solidphase synthesis of a 1,3,5-triazine scaffold has been developed. The key feature of the synthesis is the use of a readily accessible solid-supported thiouronium salt as a primary precursor for the stepwise assembly of the 1,3,5-tri-azine substrate. The sulfur linker employed in the synthesis is stable under both acidic and basic conditions and is versatile enough to provide access to monocyclic, bicyclic, and spirocyclic compounds with the 1,3,5-triazine scaffold. By using this synthetic strategy, a representative set of 79 compounds containing the 1,3,5-triazine scaffold were prepared.
- Kong, Kah Hoe,Tan, Chong Kiat,Lin, Xijie,Lam, Yulin
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experimental part
p. 1476 - 1486
(2012/03/26)
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- NEW FLUOROUS TAGGING AND SCAVENGING REACTANTS AND METHODS OF SYNTHESIS AND USE THEREOF
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The present invention includes methods and compositions for increasing the fluorous nature of an organic compound by reacting it with at least one fluorous compound to produce a fluorous tagged organic compound. The increased fluorous nature of the fluorous tagged organic compound can then be utilized to separate the fluorous organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom. The resultant fluorous tagged organic compound can be subjected to subsequent chemical transformations, wherein the fluorous nature of the tagged compound is utilized to increase the ease of separation of the fluorous tagged organic compound from untagged reagents, reactants, catalysts and/or products derived therefrom, after each chemical transformation. The chemical transformations result in a second fluorous tagged organic compound wherein the fluorous nature of the second fluorous tagged organic compound can then be reduced by removing the fluorous group therefrom, thereby producing a second organic compound that may be employed as a pharmaceutical compound or intermediate, or a combinatorial library component.
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- One-Pot Synthesis and Conformational Features of N,N′-Disubstituted Ketene Aminals
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N,N′-Disubstituted ketene aminals are bioisosteres of thioureas and are useful building blocks in many synthetic operations. A convenient one-pot synthesis of N,N′-disubstituted ketene aminals from activated methylene compounds and isothiocyanates is desc
- Shi, Yan,Zhang, Jing,Grazier, Nyeemah,Stein, Philip D.,Atwal, Karnail S.,Traeger, Sarah C.,Callahan, Sharon P.,Malley, Mary F.,Galella, Michael A.,Gougoutas, Jack Z.
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p. 188 - 191
(2007/10/03)
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- Fluorous electrophilic scavengers for solution-phase parallel synthesis
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A fluorous isatoic anhydride and isocyanate are synthesized and used as scavengers for amines in solution-phase parallel synthesis of urea, thiourea, and β-hydroxyamine analogs. The resulting fluorous derivatives are readily separated from the reaction mi
- Zhang, Wei,Chen, Christine Hiu-Tung,Nagashima, Tadamichi
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p. 2065 - 2068
(2007/10/03)
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- 9-Isothiocyanatoanthracene as a versatile starting compound in the chemistry of anthracen-9-yl derivatives
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The synthesis, structure and reactivity of 9-isothiocyanatoanthracene (5) likewise the conformation of the corresponding thioureas (6a-6i) have been studied. The 13C NMR substituent chemical shift values of the NCS group and correlations betwee
- Janovec, Ladislav,Suchar, Gejza,Imrich, Jan,Kristian, Pavol,Sasinkova, Vlasta,Alfoeldi, Juraj,Sedlak, Erik
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p. 665 - 678
(2007/10/03)
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- A convenient route to cyanoguanidines
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A facile and versatile method for the preparation of cyanoguanidines 7 from amines 3 and isothiocyanates 4 via a methylation, cyanamide-treatment sequence is described.
- Novak, Lajos,Hanania, Michel,Kovacs, Peter,Kovacs, Csilla Erika,Kolonits, Pal,Szantay, Csaba
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p. 1757 - 1766
(2007/10/03)
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- A facile conversion of symmetrical to unsymmetrical thioureas
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A convenient route for quantitative conversion of symmetrical thioureas into unsymmetrical thioureas is described. The method circumvents the use of toxic isothiocyanates and a case study is reported using 1,3-diphenylthiourea.
- Ramadas,Srinivasan,Janarthanan
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p. 6447 - 6450
(2007/10/02)
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- Chemistry on Rigid Interfaces, 8. Kinetics of Suspensions of Aminoaerosil (Aerosil Covalently Linked with 3-Aminopropylgroups) with Isothiocyanates in Homogeneous Solution
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In aminoaerosil, the products of the reaction of γ-aminopropyltriethoxysilane with aerosil, an intraparticular interaction of the basic amino groups with the acidic silanol groups is observed.This behaviour was established a) by adsorption experiments usi
- Horner, L.,Roth, W.
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p. 1333 - 1342
(2007/10/02)
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