Preparation of 2,2-disubstituted 1,2-dihydro-3H-indol-3-ones via oxidation of 2-substituted indoles and Mannich-type reaction

Chiral Phosphoric Acid-Catalyzed Pictet–Spengler Reactions for Synthesis of 5′,11′-Dihydrospiro[indoline-3,6′-indolo[3,2-c]qui-nolin]-2-ones Containing Quaternary Stereocenters

“…2-(1 H -Indolyl)­aniline derivatives 1a and 1b were prepared according to known methods. − 2-(1 H -Indolyl)­aniline derivatives 1c – 1g could be prepared according to the reported methods with minor modification. − 2-(3,5-Dimethyl-1 H -pyrrol-2-yl)­aniline 1h could be synthesized from 2,4-dimethyl-1 H -pyrrole and 2-nitrobromobenzene in two steps according to a similar report. , Among them, compounds 1a and 1b are the known compounds. , …”

2-Hydroxy-2-methyl-1-phenylindolin-3-one

“…Compounds containing the 2-hydroxyindol-3-one substructure are important intermediates in the total syntheses of some natural products including (+)-isatisine A, (±)mersicarpine, hinckdentine A, mitomycin and others (Karadeolian & Kerr, 2010;Magolan et al, 2008;Higuchi et al, 2009;Colandrea et al, 2003;Kawasaki et al, 2004). New synthetic approaches towards 2-hydroxyindol-3-ones have been reported recently (Coldham et al, 2010;Higuchi et al, 2010;Cariou et al, 2007;Hewitt & Shao, 2006; Altinis Kiraz et al, 2004). A related 2-hydroxyindol-3-one compound, alkaloid melochicorine, was found in the plant Melochicoria corchorifolia (Bhakuni et al, 1991) In the crystal structure of (I) two molecules are connected by two intermolecular O-H Table 1).…”

Recent advances in organocatalytic methods for the synthesis of disubstituted 2- and 3-indolinones

“…For instance, an organic asymmetric promoter (stoichiometric camphor sulfonic acid) was employed in the nucleophilic addition of vinyloxytrimethylsilane, furan or indole to 2-hydroxy-1,2dihydro-3H-indol-3-one, but authors did not cite if enantiomeric excess exists or not. 197 Actually, the first example of asymmetric alkylation of 2-monosubstituted indolin-3-ones with optically active phase transfer catalysts has been reported by Kawasaki's group in 2007. The alkylation of various 2-monosubstituted indolin-3-ones (212a) with alkyl halides was reported to give the desired products (215) in 68-99% yields and 12-65% ee (Scheme 80).…”