52415-29-9Relevant articles and documents
Structure and Synthesis of a New Bromoindole from a Marine Sponge
Dellar, Gregory,Djura, Peter,Sargent, Melvyn V.
, p. 1679 - 1680 (1981)
The isolation of methyl (E)-3-(6-bromoindol-3-yl)prop-2-enoate (5) from a sponge of the genus Iotrochota is described; its structure, (5), was confirmed by synthesis.
Concerning the preparation of 6-bromotryptamine
Scott Wiens,Johnson, Jerry L.,Gribble, Gordon W.
, (2021/03/15)
Most of the previous syntheses of the marine natural product 6-bromotryptamine have almost certainly led to partial debromination resulting in an impure product containing tryptamine. We show that loss of bromine occurs when lithium aluminum hydride is employed as a reducing agent in the final reaction step leading to 6-bromotryptamine. Reductive-debromination is also likely to intrude during some of the syntheses of 6-bromoindole, the typical precursor to 6-bromotryptamine. None of the seven described syntheses of 6-bromotryptamine that involve a reduction sequence from 6-bromoindole have reported elemental analyses as a measure of purity.
Novel Arylindigoids by Late-Stage Derivatization of Biocatalytically Synthesized Dibromoindigo
Schnepel, Christian,Dodero, Veronica I.,Sewald, Norbert
, p. 5404 - 5411 (2021/03/03)
Indigoids represent natural product-based compounds applicable as organic semiconductors and photoresponsive materials. Yet modified indigo derivatives are difficult to access by chemical synthesis. A biocatalytic approach applying several consecutive selective C?H functionalizations was developed that selectively provides access to various indigoids: Enzymatic halogenation of l-tryptophan followed by indole generation with tryptophanase yields 5-, 6- and 7-bromoindoles. Subsequent hydroxylation using a flavin monooxygenase furnishes dibromoindigo that is derivatized by acylation. This four-step one-pot cascade gives dibromoindigo in good isolated yields. Moreover, the halogen substituent allows for late-stage diversification by cross-coupling directly performed in the crude mixture, thus enabling synthesis of a small set of 6,6’-diarylindigo derivatives. This chemoenzymatic approach provides a modular platform towards novel indigoids with attractive spectral properties.
Applications of rare earth silicon amination material as catalyst in preparation of indole or indole derivative
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Paragraph 0068-0072, (2020/03/03)
The invention belongs to the technical field of chemical engineering, and specially provides applications of a rare earth silicon amination material as a catalyst in preparation of indole or an indolederivative, wherein the reaction raw materials comprise a compound I, the general formula of the compound I is shown in the specification, R is hydrogen, methyl, chlorine, fluorine, bromine or methoxyl, the rare earth silicon amination material M[N(SiMe3)2]3 is a catalyst, and M is a rare earth element. According to the invention, the indole or the indole derivative is prepared by taking the rareearth silicon amination material as the catalyst and taking the compound I and pinacol boron as the raw materials; the method is simple and convenient to operate and high in reaction selectivity; andthe synthesized indole derivative is good in product quality and high in yield.