104919-72-4Relevant articles and documents
Convenient indole synthesis from 2-iodoanilines and terminal alkynes by the sequential Sonogashira reaction and the cyclization reaction promoted by tetrabutylammonium fluoride (TBAF).
Suzuki, Naoyuki,Yasaki, Sakura,Yasuhara, Akito,Sakamoto, Takao
, p. 1170 - 1173 (2003)
The sequential Sonogashira reaction and the cyclization reaction of various 2-iodoanilines and terminal alkynes in the presence of a palladium catalyst and tetrabutylammonium fluoride (TBAF) gave the corresponding 2-substituted indoles in good yields.
One-pot approach to 2,3-disubstituted-2,3-dihydro-4-quinolones from 2-alkynylbenzamides
Okamoto, Noriko,Takeda, Kei,Ishikura, Minoru,Yanada, Reiko
experimental part, p. 9139 - 9143 (2011/12/16)
Concise and efficient syntheses of various trans-2,3-disubstituted-2,3- dihydro-4-quinolones have been achieved via tandem Hofmann-type rearrangement of 2-alkynylbenzamides, nucleophilic addition of alcohols to the isocyanate intermediates, intermolecular
Platinum-catalyzed, one-pot tandem synthesis of indoles and isoquinolines via sequential rearrangement of amides and aminocyclization
Okamoto, Noriko,Takeda, Kei,Yanada, Reiko
scheme or table, 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
Concise one-pot tandem synthesis of indoles and isoquinolines from amides
Okamoto, Noriko,Miwa, Yoshihisa,Minami, Hideki,Takeda, Kei,Yanada, Reiko
scheme or table, p. 9693 - 9696 (2010/04/28)
Heterocyclic hot pot: Platinum[II]-catalyzed syntheses of indoles and isoquinolines from isocyanates, which are derived from a Hofmann-type rearrangement of amides using a hypervalent iodine reagent, are described. C2-symmetric macrocyclic bis[indole]s ca
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.
Convenient synthesis of 2-substituted indoles from 2-ethynylanilines with tetrabutylammonium fluoride
Yasuhara, Akito,Kanamori, Yuichi,Kaneko, Masashi,Numata, Atsushi,Kondo, Yoshinori,Sakamoto, Takao
, p. 529 - 534 (2007/10/03)
The cyclization reaction of various 2-ethynylanilines, which were easily synthesized from 2-haloanilines by the palladium-catalyzed reaction with terminal alkynes, with tetrabutylammonium fluoride (TBAF) to yield 2-substituted indoles proceeded at refluxing or room temperature in THF in excellent yields without affecting the bromo, chloro, cyano, ethoxycarbonyl, and ethynyl groups.
Condensed Heteroaromatic Ring Systems. XIII. One-Step Synthesis of 2-Substituted 1-Methylsulfonylindoles from N-(2-Halophenyl)methanesulfonamides
Sakamoto, Takao,Kondo, Yoshinori,Iwashita, Shigeki,Nagano, Tatsuo,Yamanaka, Hiroshi
, p. 1305 - 1308 (2007/10/02)
The reaction of N-(2-bromophenyl)- and N-(2-iodophenyl)methanesulfonamide with terminal acetylenes in the presence of dichlorobis(triphenylphosphine)palladium yielded 1-methylsulfonylindoles having carbon-functional groups at the 2-position, such as hydroxymethyl, 2-hydroxyethyl, diethoxymethyl, 2-ethoxycarbonylethyl, etc., in one step.Keywords - palladium-catalyzed reaction; dichlorobis(triphenylphosphine)palladium; N-(2-halophenyl)methanesulfonamide; acetylene; 2-substituted 1-methylsulfonylindole.
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.
