The Experts below are selected from a list of 264 Experts worldwide ranked by ideXlab platform
V D Filimonov - One of the best experts on this subject based on the ideXlab platform.
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a novel convenient synthesis of pyridinyl and quinolinyl triflates and tosylates via one pot Diazotization of aminopyridines and aminoquinolines in solution
Synthesis, 2015Co-Authors: Assiya Zh Kassanova, E A Krasnokutskaya, Perizat S Beisembai, V D FilimonovAbstract:The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves Diazotization of the heterocyclic amines with sodium nitrite in mixed hexane–DMSO or hexane–DMF solutions in the presence of trifluoromethanesulfonic acid or p -toluenesulfonic acid.
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a new synthesis of pyridinyl trifluoromethanesulfonates via one pot Diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid
Tetrahedron Letters, 2014Co-Authors: E A Krasnokutskaya, Assiya Zh Kassanova, Makpal T Estaeva, V D FilimonovAbstract:Abstract The first method for the direct one-pot transformation of aminopyridines into pyridinyl trifluoromethanesulfonates is developed. The procedure involves Diazotization of aminopyridines with sodium nitrite in a DMSO paste in the presence of trifluoromethanesulfonic acid.
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a green procedure for the Diazotization iodination of aromatic amines under aqueous strong acid free conditions
Synthesis, 2011Co-Authors: Marina E Trusova, E A Krasnokutskaya, Pavel S Postnikov, Younghwa Choi, V D FilimonovAbstract:A convenient and mild one-pot method for the synthesis of iodoarenes in high yields by the sequential Diazotization-iodina- tion of aromatic amines with a reusable polymeric Diazotization agent in the presence of p-toluenesulfonic acid at room temperature in water was developed. The method is general and is the greenest alternative of the known Diazotization-iodination methods. The method is also effective for the preparation of 1H-ben- zo(d)(1,2,3)triazole and benzo(d)(1,2,3)thiadiazole.
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a new one pot solvent free synthesis of pyridinyl tosylates via Diazotization of aminopyridines
Tetrahedron Letters, 2011Co-Authors: Alexey N Tretyakov, E A Krasnokutskaya, Dmitry A Gorlushko, Vladimir D Ogorodnikov, V D FilimonovAbstract:A new, convenient, one-pot method for the synthesis of pyridinyl tosylates is developed. The procedure involves sequential Diazotization/tosylation of aminopyridines with sodium nitrite and p-toluenesulfonic acid under solvent-free conditions in a water paste at room temperature.
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a simple and efficient procedure for Diazotization iodination of aromatic amines in aqueous pastes by the action of sodium nitrite and sodium hydrogen sulfate
Russian Journal of Organic Chemistry, 2008Co-Authors: Dmitry A Gorlushko, E A Krasnokutskaya, V D Filimonov, N I Semenishcheva, Alexei N Tretyakov, Bong Seong Go, Ho Yun HwangAbstract:One of the most widely used methods of synthesis of aromatic iodides is based on Diazotization–iodina-tion of aromatic amines. The Diazotization is generally carried out using accessible sodium nitrite in strongly acidic medium at reduced temperature [1–5]. Alter-native procedures involve more expensive alkyl nitrites as diazotizing agents in the presence of diiodomethane or other sources of iodine [6, 7]. We previously pro-posed simple procedures for Diazotization–iodination with sodium nitrite at room temperature in weakly acidic media created by
E A Krasnokutskaya - One of the best experts on this subject based on the ideXlab platform.
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a new transformation of aminopyridines upon Diazotization in acetonitrile with the formation of n pyridinylacetamides
Russian Chemical Bulletin, 2016Co-Authors: A A Chudinov, E A Krasnokutskaya, R S Dovbnya, V D Ogorodnikov, I L FilimonovaAbstract:Diazotization of aminopyridines upon treatment with NaNO2 and H3PO4 in acetonitrile led to the formation of N-pyridinylacetamides. This reaction constitutes a convenient and general preparative method for the synthesis of 2-, 3-, and 4-N-pyridinylacetamides under mild conditions in good yields. The in situ oxidation of the thus obtained N-pyridinylacetamides with hydrogen peroxide gave good yields of pyridinylacetamide N-oxides.
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a novel convenient synthesis of pyridinyl and quinolinyl triflates and tosylates via one pot Diazotization of aminopyridines and aminoquinolines in solution
Synthesis, 2015Co-Authors: Assiya Zh Kassanova, E A Krasnokutskaya, Perizat S Beisembai, V D FilimonovAbstract:The first effective and simple method for the direct one-pot transformation of 2-, 3-, and 4-aminopyridines, 2,6-diaminopyridines, and 2-aminoquinoline into the corresponding pyridinyl and quinolinyl trifluoromethanesulfonates and tosylates in solvents was developed. The procedure involves Diazotization of the heterocyclic amines with sodium nitrite in mixed hexane–DMSO or hexane–DMF solutions in the presence of trifluoromethanesulfonic acid or p -toluenesulfonic acid.
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a new synthesis of pyridinyl trifluoromethanesulfonates via one pot Diazotization of aminopyridines in the presence of trifluoromethanesulfonic acid
Tetrahedron Letters, 2014Co-Authors: E A Krasnokutskaya, Assiya Zh Kassanova, Makpal T Estaeva, V D FilimonovAbstract:Abstract The first method for the direct one-pot transformation of aminopyridines into pyridinyl trifluoromethanesulfonates is developed. The procedure involves Diazotization of aminopyridines with sodium nitrite in a DMSO paste in the presence of trifluoromethanesulfonic acid.
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a green procedure for the Diazotization iodination of aromatic amines under aqueous strong acid free conditions
Synthesis, 2011Co-Authors: Marina E Trusova, E A Krasnokutskaya, Pavel S Postnikov, Younghwa Choi, V D FilimonovAbstract:A convenient and mild one-pot method for the synthesis of iodoarenes in high yields by the sequential Diazotization-iodina- tion of aromatic amines with a reusable polymeric Diazotization agent in the presence of p-toluenesulfonic acid at room temperature in water was developed. The method is general and is the greenest alternative of the known Diazotization-iodination methods. The method is also effective for the preparation of 1H-ben- zo(d)(1,2,3)triazole and benzo(d)(1,2,3)thiadiazole.
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a new one pot solvent free synthesis of pyridinyl tosylates via Diazotization of aminopyridines
Tetrahedron Letters, 2011Co-Authors: Alexey N Tretyakov, E A Krasnokutskaya, Dmitry A Gorlushko, Vladimir D Ogorodnikov, V D FilimonovAbstract:A new, convenient, one-pot method for the synthesis of pyridinyl tosylates is developed. The procedure involves sequential Diazotization/tosylation of aminopyridines with sodium nitrite and p-toluenesulfonic acid under solvent-free conditions in a water paste at room temperature.
Vivek V Ranade - One of the best experts on this subject based on the ideXlab platform.
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selectivity engineering of the Diazotization reaction in a continuous flow reactor
Reaction Chemistry and Engineering, 2016Co-Authors: Chinmay A Shukla, Amol A Kulkarni, Vivek V RanadeAbstract:In situ generated diazonium salts are useful intermediates for the synthesis of fine chemicals and active pharmaceutical ingredients. This paper presents a methodology for selectivity engineering of the Diazotization reaction in a continuous reactor. The yield of Diazotization was found to depend on mixing, dispersion, reaction kinetics, operating temperature and residence time. Initially, experimental data and an isothermal axial dispersion model were used for estimating mixing time. A correlation for estimating mixing time for different flow reactors is proposed. The model predictions were compared with the experimental data. The validated axial dispersion model and Central Composite Design (CCD) were used to optimize Diazotization in a straight tube reactor (1.78 mL). The model was then used for scaling-up of aniline Diazotization from a straight tube reactor to a proprietary AmAR3 reactor (scale-up ratio of ∼20). The initial concentration, inlet temperature, average heat capacity of the reaction mixture, mixing, residence time (distribution) and available heat transfer area per unit volume of the reactor were found to be the key parameters for scaling-up of the Diazotization reaction. The presented approach and results will be useful to practicing chemists and engineers for enhancing the selectivity of Diazotization reactions in continuous reactors.
Michael G Organ - One of the best experts on this subject based on the ideXlab platform.
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using anilines as masked cross coupling partners design of a telescoped three step flow Diazotization iododeDiazotization cross coupling process
Chemistry: A European Journal, 2016Co-Authors: Matthieu Teci, Michael Tilley, Michael A Mcguire, Michael G OrganAbstract:The conversion of commercially available anilines into biaryl and biarylacetylene products was realized by using a telescoped, three-reactor flow Diazotization/iododeDiazotization/cross-coupling process. The segmented flow stream created by off-gassing during the Sandmeyer sequence was restored to a continuous column of reaction solution by using a specially designed continuous-flow unit controlled by custom software created in-house. The resultant aryl iodide was then combined with a stream of cross-coupling solution that fed into the final reactor. The system proved versatile as modifications to the Diazotization/iododeDiazotization sequence could be made rapidly to account for any substrate specificity (e.g., solubility problems), leading to a wide substrate scope of Suzuki–Miyaura and Sonogashira cross-coupled products.
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handling hazards using continuous flow chemistry synthesis of n1 aryl 1 2 3 triazoles from anilines via telescoped three step Diazotization azidodeDiazotization and 3 2 dipolar cycloaddition processes
Organic Process Research & Development, 2016Co-Authors: Matthieu Teci, Michael Tilley, Michael A Mcguire, Michael G OrganAbstract:The conversion of commercially available anilines into triazole products was realized using a telescoped three-reactor flow Diazotization, azidodeDiazotization, and [3 + 2] dipolar cycloaddition process. The Diazotization–azidodeDiazotization sequence was accelerated by means of an ultrasonic bath resulting in a degassed, segmented effluent. An automated continuous flow unit controlled by custom software created in-house was used to collect the aryl azide stream and restore it to a continuous column of the reagent. When combined with a variety of dipolarophiles, 1-aryl-[1,2,3]-triazoles were thus assembled by either copper catalyzed alkyne–azide cycloaddition (CuAAC) or Huisgen cycloaddition reactions.
Chinmay A Shukla - One of the best experts on this subject based on the ideXlab platform.
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selectivity engineering of the Diazotization reaction in a continuous flow reactor
Reaction Chemistry and Engineering, 2016Co-Authors: Chinmay A Shukla, Amol A Kulkarni, Vivek V RanadeAbstract:In situ generated diazonium salts are useful intermediates for the synthesis of fine chemicals and active pharmaceutical ingredients. This paper presents a methodology for selectivity engineering of the Diazotization reaction in a continuous reactor. The yield of Diazotization was found to depend on mixing, dispersion, reaction kinetics, operating temperature and residence time. Initially, experimental data and an isothermal axial dispersion model were used for estimating mixing time. A correlation for estimating mixing time for different flow reactors is proposed. The model predictions were compared with the experimental data. The validated axial dispersion model and Central Composite Design (CCD) were used to optimize Diazotization in a straight tube reactor (1.78 mL). The model was then used for scaling-up of aniline Diazotization from a straight tube reactor to a proprietary AmAR3 reactor (scale-up ratio of ∼20). The initial concentration, inlet temperature, average heat capacity of the reaction mixture, mixing, residence time (distribution) and available heat transfer area per unit volume of the reactor were found to be the key parameters for scaling-up of the Diazotization reaction. The presented approach and results will be useful to practicing chemists and engineers for enhancing the selectivity of Diazotization reactions in continuous reactors.