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Andrey A. Tolmachev - One of the best experts on this subject based on the ideXlab platform.
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protecting group free synthesis of carboxyl substituted dihydropyrimidines through biginelli reaction
Journal of Heterocyclic Chemistry, 2013Co-Authors: Sergey V. Ryabukhin, Andrey S. Plaskon, Andrey A. Tolmachev, Eugeniy N Ostapchuk, Oleksandr O GrygorenkoAbstract:Chlorotrimethylsilane-promoted Biginelli-type reaction of benzaldehyde, acetoacetic acid derivatives, and various carboxyl-containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono-substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one-pot, protecting group free synthesis of dihydropyrimidines possessing carboxylic functionality.
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Chlorotrimethylsilane promoted condensation of ketones and aminoazoles
ChemInform, 2013Co-Authors: Sergey V. Ryabukhin, Vasiliy S Naumchik, Oleksandr O Grygorenko, Andrey A. TolmachevAbstract:Tms-Cl-promoted reaction of aminoazoles with ketones (II) provides dihydroazolopyrimidine derivatives such as (III) and (V) as single regioisomers.
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application of Chlorotrimethylsilane in pictet spengler reaction
ChemInform, 2013Co-Authors: Sergey V. Ryabukhin, Dmitriy M. Panov, Andrey S. Plaskon, Andrey A. Tolmachev, Radomyr V. SmaliyAbstract:A variety of tetrahydro-β-carbolines and their analogues is readily prepared by Chlorotrimethylsilane-promoted Pictet—Spengler reaction (33 examples).
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Chlorotrimethylsilane promoted condensation of ketones and aminoazoles
Journal of Heterocyclic Chemistry, 2012Co-Authors: Sergey V. Ryabukhin, Andrey A. Tolmachev, Vasiliy S Naumchik, Oleksandr O GrygorenkoAbstract:Chlorotrimethylsilane-promoted reaction of ketones and aminoazoles (i.e., 3-amino-1,2,4-triazoles, 5-aminotetrazole) at 2 : 1 ratio resulted in the formation of 4,5-dihydroazolo[1,5-a]pyrimidine derivatives as the single regioisomers in 35 – 71% yields. In the case of tert-butylmethylketone and 5-aminotetrazole as the starting materials, the solvent (dimethylformamide) entered the reaction instead of the second ketone molecule.
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application of Chlorotrimethylsilane in pictet spengler reaction
Monatshefte Fur Chemie, 2012Co-Authors: Sergey V. Ryabukhin, Dmitriy M. Panov, Andrey S. Plaskon, Andrey A. Tolmachev, Radomyr V. SmaliyAbstract:Chlorotrimethylsilane has been found to be an efficient condensing agent in the Pictet–Spengler reaction, affording an extremely straightforward synthetic route to tetrahydro-β-carboline derivatives and their analogs. The applicability of the method has been studied, and a representative library of structurally diverse products has been created. .
Sergey V. Ryabukhin - One of the best experts on this subject based on the ideXlab platform.
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protecting group free synthesis of carboxyl substituted dihydropyrimidines through biginelli reaction
Journal of Heterocyclic Chemistry, 2013Co-Authors: Sergey V. Ryabukhin, Andrey S. Plaskon, Andrey A. Tolmachev, Eugeniy N Ostapchuk, Oleksandr O GrygorenkoAbstract:Chlorotrimethylsilane-promoted Biginelli-type reaction of benzaldehyde, acetoacetic acid derivatives, and various carboxyl-containing ureas was explored. It was found that the steric load of the urea substituents influenced strongly the reaction outcome; in particular, the method was efficient only in the case of unbranched mono-substituted ureas bearing either aliphatic or aromatic groups. The method allows performing a one-pot, protecting group free synthesis of dihydropyrimidines possessing carboxylic functionality.
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Chlorotrimethylsilane promoted condensation of ketones and aminoazoles
ChemInform, 2013Co-Authors: Sergey V. Ryabukhin, Vasiliy S Naumchik, Oleksandr O Grygorenko, Andrey A. TolmachevAbstract:Tms-Cl-promoted reaction of aminoazoles with ketones (II) provides dihydroazolopyrimidine derivatives such as (III) and (V) as single regioisomers.
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application of Chlorotrimethylsilane in pictet spengler reaction
ChemInform, 2013Co-Authors: Sergey V. Ryabukhin, Dmitriy M. Panov, Andrey S. Plaskon, Andrey A. Tolmachev, Radomyr V. SmaliyAbstract:A variety of tetrahydro-β-carbolines and their analogues is readily prepared by Chlorotrimethylsilane-promoted Pictet—Spengler reaction (33 examples).
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Chlorotrimethylsilane promoted condensation of ketones and aminoazoles
Journal of Heterocyclic Chemistry, 2012Co-Authors: Sergey V. Ryabukhin, Andrey A. Tolmachev, Vasiliy S Naumchik, Oleksandr O GrygorenkoAbstract:Chlorotrimethylsilane-promoted reaction of ketones and aminoazoles (i.e., 3-amino-1,2,4-triazoles, 5-aminotetrazole) at 2 : 1 ratio resulted in the formation of 4,5-dihydroazolo[1,5-a]pyrimidine derivatives as the single regioisomers in 35 – 71% yields. In the case of tert-butylmethylketone and 5-aminotetrazole as the starting materials, the solvent (dimethylformamide) entered the reaction instead of the second ketone molecule.
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application of Chlorotrimethylsilane in pictet spengler reaction
Monatshefte Fur Chemie, 2012Co-Authors: Sergey V. Ryabukhin, Dmitriy M. Panov, Andrey S. Plaskon, Andrey A. Tolmachev, Radomyr V. SmaliyAbstract:Chlorotrimethylsilane has been found to be an efficient condensing agent in the Pictet–Spengler reaction, affording an extremely straightforward synthetic route to tetrahydro-β-carboline derivatives and their analogs. The applicability of the method has been studied, and a representative library of structurally diverse products has been created. .
Jason S. Tedrow - One of the best experts on this subject based on the ideXlab platform.
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magnesium halide catalyzed anti aldol reactions of chiral n acylthiazolidinethiones
Organic Letters, 2002Co-Authors: David A. Evans, Jared T Shaw, Wade C Downey, Jason S. TedrowAbstract:Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and Chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.
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magnesium halide catalyzed anti aldol reactions of chiral n acylthiazolidinethiones
Organic Letters, 2002Co-Authors: David A. Evans, Jared T Shaw, Wade C Downey, Jason S. TedrowAbstract:Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and Chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.
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diastereoselective magnesium halide catalyzed anti aldol reactions of chiral n acyloxazolidinones
Journal of the American Chemical Society, 2002Co-Authors: David A. Evans, Jared T Shaw, Jason S. Tedrow, Wade C DowneyAbstract:A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with Chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
Wade C Downey - One of the best experts on this subject based on the ideXlab platform.
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magnesium halide catalyzed anti aldol reactions of chiral n acylthiazolidinethiones
Organic Letters, 2002Co-Authors: David A. Evans, Jared T Shaw, Wade C Downey, Jason S. TedrowAbstract:Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and Chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.
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magnesium halide catalyzed anti aldol reactions of chiral n acylthiazolidinethiones
Organic Letters, 2002Co-Authors: David A. Evans, Jared T Shaw, Wade C Downey, Jason S. TedrowAbstract:Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and Chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.
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diastereoselective magnesium halide catalyzed anti aldol reactions of chiral n acyloxazolidinones
Journal of the American Chemical Society, 2002Co-Authors: David A. Evans, Jared T Shaw, Jason S. Tedrow, Wade C DowneyAbstract:A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with Chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.
David A. Evans - One of the best experts on this subject based on the ideXlab platform.
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magnesium halide catalyzed anti aldol reactions of chiral n acylthiazolidinethiones
Organic Letters, 2002Co-Authors: David A. Evans, Jared T Shaw, Wade C Downey, Jason S. TedrowAbstract:Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and Chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.
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magnesium halide catalyzed anti aldol reactions of chiral n acylthiazolidinethiones
Organic Letters, 2002Co-Authors: David A. Evans, Jared T Shaw, Wade C Downey, Jason S. TedrowAbstract:Diastereoselective direct aldol reactions of chiral N-acylthiazolidinethiones occur in high yield with preference for the illustrated anti diastereomer. This reaction is catalyzed by 10% MgBr2·OEt2 in the presence of triethylamine and Chlorotrimethylsilane. Yields range from 56 to 93% with diastereoselectivity up to 19:1 for a variety of N-acylthiazolidinethiones and unsaturated aldehydes.
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diastereoselective magnesium halide catalyzed anti aldol reactions of chiral n acyloxazolidinones
Journal of the American Chemical Society, 2002Co-Authors: David A. Evans, Jared T Shaw, Jason S. Tedrow, Wade C DowneyAbstract:A chiral auxilliary-based direct aldol reaction is reported. The reactions are catalytic in magnesium salts and are facilitated by silylation with Chlorotrimethylsilane. The adducts isolated are in high diastereoselectivity (up to 32:1 dr) and favor the anti-aldol diastereomer B. Reactions are operationally simple and can be run under ambient atmosphere without rigorous exclusion of water. Many of the adducts are highly crystalline and a single diastereomer can be isolated without chromatography.