104919-71-3Relevant academic research and scientific papers
Platinum-catalyzed, one-pot tandem synthesis of indoles and isoquinolines via sequential rearrangement of amides and aminocyclization
Okamoto, Noriko,Takeda, Kei,Yanada, Reiko
experimental part, p. 7615 - 7625 (2011/02/25)
By using platinum(II) chloride as a Lewis acid catalyst, concise and efficient syntheses of indole carbamates, 1,2-dihydroisoquinoline carbamates, macrocyclic indole carbamates, indole ureas, and indole phosphoranes have been achieved via tandem Hofmann-t
Development of an Efficient Procedure for Indole Ring Synthesis from 2-Ethynylaniline Derivatives Catalyzed by Cu(II) Salts and Its Application to Natural Product Synthesis
Hiroya, Kou,Itoh, Shin,Sakamoto, Takao
, p. 1126 - 1136 (2007/10/03)
The development of efficient methods for the indole synthesis catalyzed by Cu(II) salts and its applications were investigated. Cu(OAc)2 has been proved to be the best catalyst for the synthesis of various 1-p-tolylsulfonyl or 1-methylsulfonylindoles, which have both electron-withdrawing and electron-donating groups on the aromatic ring and C2 position of indoles. For the primary aniline derivatives, Cu(OCOCF 3)2 showed good activities, while Cu(OAc)2 was a good catalyst for the cyclization of secondary anilines. This methodology could be applied to the sequential cyclization reaction for the compounds which have the electrophilic part in the same molecule. By prior treatment with KH, the sequential cyclization was realized to provide the tricyclic ring systems, but it was limited to five- and six-membered rings for the second cyclization. Finally, formal and total synthesis of hippadine with the Cu(II)-promoted indole synthesis as the key step was accomplished.
Condensed Heteroaromatic Ring Systems. XII. Synthesis of Indole Derivatives from Ethyl 2-Bromocarbanilates
Sakamoto, Takao,Kondo, Yoshinori,Iwashita, Shigeki,Yamanaka, Hiroshi
, p. 1823 - 1828 (2007/10/02)
The palladium-catalyzed reaction of ethyl 2-bromocarbanilate with trimethylsilylacetylene yielded ethyl 2-(trimethylsilylethynyl)carbanilate, which was treated with sodium ethoxide to give indole.The carbanilates having a methyl or a bromo substituent were similarly transformed to corresponding indole derivatives.Furthermore, pyrrolo- and Pyrrolopyridines were synthesized by this method.Keywords---palladium-catalyzed reaction; trimethylsilylacetylene; ethyl 2-halocarbanilate; ethyl 2-halopyridinecarbamate; ethyl 2-(trimethylsilylethynyl)carbanylate; ethyl o-(trimethylsilylethynyl)pyridinecarbamate;indole;pyrrolopyridine
FACILE SYNTHESIS OF 2-SUBSTITUTED INDOLES FROM o-BROMOANILINE
Sakamoto, Takao,Kondo, Yoshinori,Yamanaka, Hiroshi
, p. 31 - 32 (2007/10/02)
The condensation of ethyl o-bromocarbanilate (4) with trimethylsilylacetylene in the presence of dichlorobis(triphenylphosphine)palladium, followed by treatment with sodium ethoxide in boiling ethanol gave indole (3a) in 72percent overall yield from 4.Similarly, 2-substituted indoles (3b,c) were synthesized from 4 and the corresponding 1-alkynes.
