- A Bioinspired Synthesis of Polyfunctional Indoles
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Polyfunctional indoles bearing substituents at C5 and C6 are prevalent in natural products, pharmaceuticals, agrochemicals, and materials. Owing to the remoteness of the C5 and C6 positions, indoles of this family can be difficult to prepare, and often require multistep syntheses. Herein, we describe a concise process that converts simple derivatives of tyrosine into 5,6-difunctionalized indoles by direct oxidation of C?H, N?H, and O?H bonds. Our work draws inspiration from the biosynthetic polymerization of tyrosine to make melanin pigments, but makes an important departure to provide well-defined indole heterocycles.
- Huang, Zheng,Kwon, Ohhyeon,Huang, Haiyan,Fadli, Aziz,Marat, Xavier,Moreau, Magali,Lumb, Jean-Philip
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p. 11963 - 11967
(2018/09/11)
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- A water-soluble eumelanin polymer with typical polyelectrolyte behaviour by triethyleneglycol N-functionalization
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N-functionalization of 5,6-dihydroxyindole with a hydrophilic triethyleneglycol (TEG) chain provides access to a new class of water-soluble eumelanin-like materials with relatively high dielectric constant and polyelectrolyte behaviour, reflecting enhanced charge transport by in-depth incorporation of hydration networks. This journal is
- Cicco, Stefania R.,Ambrico, Marianna,Ambrico, Paolo F.,Talamo, Maurizio Mastropasqua,Cardone, Antonio,Ligonzo, Teresa,Di Mundo, Rosa,Giannini, Cinzia,Sibillano, Teresa,Farinola, Gianluca M.,Manini, Paola,Napolitano, Alessandra,Criscuolo, Valeria,D'Ischia, Marco
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p. 2810 - 2816
(2015/03/30)
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- Efficient synthesis of 5,6-dihydroxyindole dimers, key eumelanin building blocks, by a unified o-ethynylaniline-based strategy for the construction of 2-linked biindolyl scaffolds
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(Chemical Equation Presented) A unified convenient strategy for the synthesis of 5,6-dihydroxyindole-derived 2,7′-, 2,2′-, and 2,3′-biindolyls is reported, which is based on proper manipulation of key o-ethynylaniline precursors. By the same methodology 5
- Capelli, Luigia,Manini, Paola,Pezzella, Alessandro,Napolitano, Alessandra,D'Ischia, Marco
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supporting information; experimental part
p. 7191 - 7194
(2009/12/09)
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- Total synthesis of 5,5′,6,6′-tetrahydroxy-3,3′-biindolyl, the proposed structure of a potent antioxidant found in beetroot (Beta vulgaris)
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5,5′,6,6′-Tetrahydroxy-3,3′-biindolyl, the proposed structure of a phenolic antioxidant isolated from the red beetroot (Beta vulgaris), has been synthesised. The spectroscopic data of the synthetic material is not consistent with that reported for the natural product.
- Mee, Simon P. H.,Lee, Victor,Baldwin, Jack E.,Cowley, Andrew
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p. 3695 - 3712
(2007/10/03)
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- Expedient synthesis of 5,6-dihydroxyindole and derivatives via an improved Zn(II)-assisted 2,β-dinitrostyrene approach
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A facile 3-step synthesis of 5,6-dihydroxyindole (4a) is reported, featuring the Zn(II)-controlled regioselective nitration of 3,4- dihydroxynitrostyrene (2) with tetranitromethane at pH 8.0, and the reductive cyclization of the resulting 4,5-dihydroxy-2,β-dinitrostyrene (3a) with Na2S2O4/Zn(II) at pH 4. The latter procedure was successfully extended to the conversion of the 2,β-dinitrostyrenes 3b and 3c to 5,6-dibenzyloxyindole (4b) and 5,6-diacetoxyindole (4c) in good-to-high yields.
- Novellino, Luisa,D'Ischia, Marco,Prota, Giuseppe
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p. 793 - 796
(2007/10/03)
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- Intermediates for indoles
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Ortho-nitrotoluenes are condensed with formamide acetals to yield the corresponding otho-nitro-β-aminestyrenes which undergo cyclization upon reduction to yield indoles.
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