112475-54-4Relevant articles and documents
Magnesiation of indoles with magnesium amide bases
Kondo, Yoshinori,Yoshida, Akihiro,Sakamoto, Takao
, p. 2331 - 2332 (1996)
1-Substituted indole derivatives are deprotonated with Hauser bases (R2NMgBr) or magnesium diamide [(R2N)2-Mg] to give magnesioindoles which are then reacted with electrophiles.
The synthesis of 2- and 3-aryl indoles and 1,3,4,5-tetrahydropyrano[4,3-b]indoles and their antibacterial and antifungal activity
Leboho, Tlabo C.,Michael, Joseph P.,van Otterlo, Willem A.L.,van Vuuren, Sandy F.,de Koning, Charles B.
scheme or table, p. 4948 - 4951 (2009/12/24)
A series of 2- and 3-aryl substituted indoles and two 1,3,4,5-tetrahydropyrano[4,3-b]indoles were synthesized from indole and 5-methoxyindole. The 2-aryl indoles were synthesized from the 1-(phenylsulfonyl)indole derivatives using magnesiation followed by iodination. The 2-iodinated compounds were then subjected to Suzuki-Miyaura reactions. In addition, the 3-aryl indoles were made from the corresponding 3-bromoindoles using Suzuki-Miyaura reactions. The 1,3,4,5-tetrahydropyrano[4,3-b]indoles were also synthesized from 1-(phenylsulfonyl)indole by magnesiation followed by treatment with allylbromide. The product was then converted into [2-allyl-1-(phenylsulfonyl)-1H-indol-3-yl]methanol which upon exposure to Hg(OAc)2 and NaBH4 afforded tetrahydropyrano[4,3-b]indoles. A number of the 2- and 3-aryl indoles displayed noteworthy antimicrobial activity, with compound 13a displaying the most significant activity (3.9 μg/mL) against the Gram-positive micro-organism Bacillus cereus.
Preparation and reactions of lithium indolyl(dimethyl)zincates
Kondo, Yoshinori,Takazawa, Nobuo,Yoshida, Akihiro,Sakamoto, Takao
, p. 1207 - 1208 (2007/10/02)
Lithium indol-3-yl(dimethyl)zincates, prepared by halogen-zinc exchange of 3-iodo-1-phenylsulfonylindoles with lithium trimethylzincate, reacted with benzaldehyde to give the corresponding alcohols.