3189-13-7Relevant articles and documents
Diaryliodonium Salt-Based Synthesis of N-Alkoxyindolines and Further Insights into the Ishikawa Indole Synthesis
Ogura, Akihiro,Shibata, Kouhei,Takao, Ken-Ichi
, p. 10067 - 10087 (2021/07/26)
A diaryliodonium salt-based strategy enabled the first systematic synthesis of rarely accessible N-alkoxyindolines. Mechanistic analyses suggested that the reaction likely involves reductive elimination of iodobenzene from iodaoxazepine via a four-membered transition state, followed by Meisenheimer rearrangement. Substrates with N-carbamate protection afforded indole in a manner similar to that of the Ishikawa indole synthesis. Preinstallation of a stannyl group as an iodonium salt precursor greatly expanded the substrate scope, and further mechanistic insights are discussed.
Preparation method of indole compound
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Paragraph 0038-0039, (2020/12/29)
The invention discloses a preparation method of a novel efficient indole compound, which comprises the following steps: by using o-nitroalkylbenzene containing various substituents as a raw material,controlling the reaction temperature to be 70-160 DEG C in an organic solution under the protection of inert gas and the participation of inorganic base, thereby obtaining the indole compound; preparing the novel indole compound containing various substituent groups through a hydrocarbon activation reaction catalyzed by a metal rhodium catalyst. The synthetic method is not reported in literature,the raw materials are easy to synthesize, no reducing agent needs to be added additionally, the method is simple in step, the indole compound containing various substituent groups does not need to beconstructed in one step through a nitroso intermediate, and the yield is high; The method is simple in unit operation, low in equipment requirement and suitable for rapidly synthesizing the indole compounds containing various substituent groups.
Optimizing ligand structure for low-loading and fast catalysis for alkynyl-alcohol and-amine cyclization
Stubbs, James M.,Bridge, Benjamin J.,Blacquiere, Johanna M.
, p. 7928 - 7937 (2019/06/13)
A series of [Ru(Cp/Cp?)(PR2NR′2)(MeCN)]PF6 complexes were prepared, in which the steric and electronic properties of the primary coordination sphere were varied (R = Ph, t-Bu, Bn; and Cp vs. Cp?). These complexes were catalytically active in the cyclization of alkyne substrates with an intramolecular nucleophile (amine or alcohol) to produce 5-and 6-membered heterocycles. The effect of the 1° coordination sphere structure on catalyst performance was evaluated. Steric bulk around the metal centre was a key feature to achieve rapid catalysis at low temperatures. The catalyst [Ru(Cp)(Pt-Bu2NPh2)(MeCN)]PF6 gave a turnover number that was >1 order of magnitude more active than previous catalysts in the cyclization of the benchmark substrate 2-ethynylaniline. This catalyst is tolerant of a diversity of functional groups and is competent at the formation of various substituted indoles.
