The Experts below are selected from a list of 18 Experts worldwide ranked by ideXlab platform
Eric E. Boros - One of the best experts on this subject based on the ideXlab platform.
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A Scalable Nenitzescu Synthesis of 2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile.
ChemInform, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip Stewart TurnbullAbstract:The title compound (VIII) is a key intermediate in the Synthesis of selective androgen receptor modulators.
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a scalable Nenitzescu Synthesis of 2 methyl 4 trifluoromethyl 1h indole 5 carbonitrile
Journal of Heterocyclic Chemistry, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip TurnbullAbstract:2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a key intermediate in the Synthesis of selective androgen receptor modulators discovered in these laboratories. A practical and convergent Synthesis of the title compound starting from 4-nitro-3-(trifluoromethyl)phenol and tert-butyl acetoacetate was developed, including a telescoped procedure for Synthesis (without isolation) and Nenitzescu reaction of 2-trifluoromethyl-1,4-benzoquinone. Conversion of the known Nenitzescu indole product to a novel triflate intermediate followed by palladium-catalyzed cyanation afforded a penultimate carbonitrile. Removal of the C-3 tert-butyl ester group on the indole through a decarboxylative pathway completed the Synthesis of the title compound in six steps (27% overall yield) from 4-nitro-3-(trifluoromethyl)phenol (five steps, 37% overall yield from tert-butyl acetoacetate). J. Heterocyclic Chem., (2011).
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A scalable Nenitzescu Synthesis of 2‐methyl‐4‐(trifluoromethyl)‐1H‐indole‐5‐carbonitrile
Journal of Heterocyclic Chemistry, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip Stewart TurnbullAbstract:2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a key intermediate in the Synthesis of selective androgen receptor modulators discovered in these laboratories. A practical and convergent Synthesis of the title compound starting from 4-nitro-3-(trifluoromethyl)phenol and tert-butyl acetoacetate was developed, including a telescoped procedure for Synthesis (without isolation) and Nenitzescu reaction of 2-trifluoromethyl-1,4-benzoquinone. Conversion of the known Nenitzescu indole product to a novel triflate intermediate followed by palladium-catalyzed cyanation afforded a penultimate carbonitrile. Removal of the C-3 tert-butyl ester group on the indole through a decarboxylative pathway completed the Synthesis of the title compound in six steps (27% overall yield) from 4-nitro-3-(trifluoromethyl)phenol (five steps, 37% overall yield from tert-butyl acetoacetate). J. Heterocyclic Chem., (2011).
Philip Stewart Turnbull - One of the best experts on this subject based on the ideXlab platform.
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A Scalable Nenitzescu Synthesis of 2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile.
ChemInform, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip Stewart TurnbullAbstract:The title compound (VIII) is a key intermediate in the Synthesis of selective androgen receptor modulators.
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A scalable Nenitzescu Synthesis of 2‐methyl‐4‐(trifluoromethyl)‐1H‐indole‐5‐carbonitrile
Journal of Heterocyclic Chemistry, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip Stewart TurnbullAbstract:2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a key intermediate in the Synthesis of selective androgen receptor modulators discovered in these laboratories. A practical and convergent Synthesis of the title compound starting from 4-nitro-3-(trifluoromethyl)phenol and tert-butyl acetoacetate was developed, including a telescoped procedure for Synthesis (without isolation) and Nenitzescu reaction of 2-trifluoromethyl-1,4-benzoquinone. Conversion of the known Nenitzescu indole product to a novel triflate intermediate followed by palladium-catalyzed cyanation afforded a penultimate carbonitrile. Removal of the C-3 tert-butyl ester group on the indole through a decarboxylative pathway completed the Synthesis of the title compound in six steps (27% overall yield) from 4-nitro-3-(trifluoromethyl)phenol (five steps, 37% overall yield from tert-butyl acetoacetate). J. Heterocyclic Chem., (2011).
Andrey F. Mironov - One of the best experts on this subject based on the ideXlab platform.
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The role of a Lewis acid in the Nenitzescu indole Synthesis
Tetrahedron Letters, 2008Co-Authors: Valeriya S. Velezheva, Andrey I. Sokolov, Albert G. Kornienko, Konstantin A. Lyssenko, Yulia V. Nelyubina, Ivan A. Godovikov, Alexander S. Peregudov, Andrey F. MironovAbstract:Abstract A highly efficient Lewis acid-catalyzed method for the Nenitzescu Synthesis of 5-hydroxyindoles with a range of substituents at N-1 and C-3 and symmetric 5,5′-dihydroxydiindoles has been developed. The amount of the catalyst (10–100 mol %) required depended on the nature of the enaminone component. It has been shown that Lewis acid plays a role in enaminone component activation through an enamine-ZnC12 complex followed by its deprotonation.
Istvan Kaldor - One of the best experts on this subject based on the ideXlab platform.
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A Scalable Nenitzescu Synthesis of 2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile.
ChemInform, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip Stewart TurnbullAbstract:The title compound (VIII) is a key intermediate in the Synthesis of selective androgen receptor modulators.
-
a scalable Nenitzescu Synthesis of 2 methyl 4 trifluoromethyl 1h indole 5 carbonitrile
Journal of Heterocyclic Chemistry, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip TurnbullAbstract:2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a key intermediate in the Synthesis of selective androgen receptor modulators discovered in these laboratories. A practical and convergent Synthesis of the title compound starting from 4-nitro-3-(trifluoromethyl)phenol and tert-butyl acetoacetate was developed, including a telescoped procedure for Synthesis (without isolation) and Nenitzescu reaction of 2-trifluoromethyl-1,4-benzoquinone. Conversion of the known Nenitzescu indole product to a novel triflate intermediate followed by palladium-catalyzed cyanation afforded a penultimate carbonitrile. Removal of the C-3 tert-butyl ester group on the indole through a decarboxylative pathway completed the Synthesis of the title compound in six steps (27% overall yield) from 4-nitro-3-(trifluoromethyl)phenol (five steps, 37% overall yield from tert-butyl acetoacetate). J. Heterocyclic Chem., (2011).
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A scalable Nenitzescu Synthesis of 2‐methyl‐4‐(trifluoromethyl)‐1H‐indole‐5‐carbonitrile
Journal of Heterocyclic Chemistry, 2011Co-Authors: Eric E. Boros, Istvan Kaldor, Philip Stewart TurnbullAbstract:2-Methyl-4-(trifluoromethyl)-1H-indole-5-carbonitrile is a key intermediate in the Synthesis of selective androgen receptor modulators discovered in these laboratories. A practical and convergent Synthesis of the title compound starting from 4-nitro-3-(trifluoromethyl)phenol and tert-butyl acetoacetate was developed, including a telescoped procedure for Synthesis (without isolation) and Nenitzescu reaction of 2-trifluoromethyl-1,4-benzoquinone. Conversion of the known Nenitzescu indole product to a novel triflate intermediate followed by palladium-catalyzed cyanation afforded a penultimate carbonitrile. Removal of the C-3 tert-butyl ester group on the indole through a decarboxylative pathway completed the Synthesis of the title compound in six steps (27% overall yield) from 4-nitro-3-(trifluoromethyl)phenol (five steps, 37% overall yield from tert-butyl acetoacetate). J. Heterocyclic Chem., (2011).
Valeriya S. Velezheva - One of the best experts on this subject based on the ideXlab platform.
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The role of a Lewis acid in the Nenitzescu indole Synthesis
Tetrahedron Letters, 2008Co-Authors: Valeriya S. Velezheva, Andrey I. Sokolov, Albert G. Kornienko, Konstantin A. Lyssenko, Yulia V. Nelyubina, Ivan A. Godovikov, Alexander S. Peregudov, Andrey F. MironovAbstract:Abstract A highly efficient Lewis acid-catalyzed method for the Nenitzescu Synthesis of 5-hydroxyindoles with a range of substituents at N-1 and C-3 and symmetric 5,5′-dihydroxydiindoles has been developed. The amount of the catalyst (10–100 mol %) required depended on the nature of the enaminone component. It has been shown that Lewis acid plays a role in enaminone component activation through an enamine-ZnC12 complex followed by its deprotonation.
