Syntheses of 4-, 5-, 6-, and 7-substituted tryptamine derivatives and the use of a bromine atom as a protecting group
Orthogonal syntheses of 4-, 5-, 6-, and 7-chloro substituted tryptamine derivatives were performed under the Grandberg–Zuyanova-modified Fisher indole-synthesis conditions. In the 4- and 6-substituted tryptamine cases, a bromine atom was utilized as an easily cleavable protecting group, which allowe...
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| Veröffentlicht in: | Tetrahedron letters 2014-01, Vol.55 (4), p.830-833 |
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| creator | René, Olivier Fauber, Benjamin P. |
| description | Orthogonal syntheses of 4-, 5-, 6-, and 7-chloro substituted tryptamine derivatives were performed under the Grandberg–Zuyanova-modified Fisher indole-synthesis conditions. In the 4- and 6-substituted tryptamine cases, a bromine atom was utilized as an easily cleavable protecting group, which allowed complete regiocontrol. In addition, a chlorine substituent was preserved in the debromination step and could be utilized as a synthetic handle for late-stage diversification under modern Pd(0) catalysis conditions. |
| doi_str_mv | 10.1016/j.tetlet.2013.12.025 |
| format | Article |
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| ispartof | Tetrahedron letters, 2014-01, Vol.55 (4), p.830-833 |
| issn | 0040-4039 1873-3581 |
| language | eng |
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| source | Elsevier ScienceDirect Journals |
| subjects | Bromine Catalysis Chlorine Derivatives Fisher indole synthesis Handles Late-stage functionalization Protecting group Tetrahedrons Tryptamine Tryptamines |
| title | Syntheses of 4-, 5-, 6-, and 7-substituted tryptamine derivatives and the use of a bromine atom as a protecting group |
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