108665-94-7Relevant articles and documents
Catalytic C-2 Allylation of Indoles by Electronic Modulation of the Indole Ring and its Application to the Synthesis of Functionalized Carbazoles
Lee, Ju Young,Ha, Hyeri,Bae, Seri,Han, Inhyuk,Joo, Jung Min
, p. 3458 - 3470 (2016)
We report a palladium-catalyzed C-2 allylation of indoles and subsequent cyclization of the allylated indoles. The electronic effects of chloro and ester groups that can be readily installed at the C-3 position of indoles facilitated a highly efficient C–H allylation at the C-2 position. The resulting 2-allyl-3-chloroindoles were found to be suitable substrates for benzannulation reactions with alkynes and norbornadiene as an acetylene synthon. This approach, utilizing readily available indoles, allyl acetates, and norbornadiene, allows a rapid access to complex carbazoles. (Figure presented.).
Unusual Reactions of Magnesium Indolates with Benzenesulfonyl Chloride
Wenkert, Ernest,Moeller, Peter D. R.,Piettre, Serge R.,McPhail, Andrew T.
, p. 3404 - 3409 (2007/10/02)
Grignard reagents from N-unsubstituted indoles and benzenesulfonyl chloride undergo reaction such as to produce unstable intermediates of β-chlorination and α-sulfonylation, which are transformed into oxindoles or substituted indoles.In the same reaction, yuehchukene (the naturally occurring dehydroprenylindole dimer) is converted into a spirooxindole, containing a strained four-membered ring, which is changed into a spirooxindole isomer with ring expansion on mild acid treatment.
