A Pd-based regioselective strategy to indole-1,2-fused 8- and 9-membered rings: their evaluation as potential scaffolds for apoptosis in zebrafish

Abstract

A strategy based on Pd-mediated ring closure of 1,2-disubstituted indoles containing an unactivated olefin leading to indole-1,2-fused 8- and 9-membered rings has been developed for the identification of new and potential scaffolds for apoptosis. A large number of fused indole derivatives containing an endocyclic double bond were synthesized using this robust methodology. A representative compound showed promising apoptotic properties in zebrafish embryos.

KOtBu-Mediated Aerobic Transition-Metal-Free Regioselective β-Arylation of Indoles: Synthesis of β-(2-/4-Nitroaryl)-indoles

“…Construction of unsymmetrically N -substituted ( N -R′ and N -R″) indoloindoles has been achieved earlier by Pal et al from C-α amination of indoles using 2-iodo- N -aryl­sulfonyl­amines followed by ring closing, Pd-catalyzed coupling of the β-C–H bond with the C–I bond of amines . Moreover, synthesis of indolo[3,2 b ]indoles with both free N–H has not been documented . Here synthesis of indoloindoles 28 – 29 has been accomplished by heating β-(2-nitrophenyl)-indoles 22 and 24 in P(OEt) 3 at 150 °C.…”

Synthesis of pyrido[1,2-a]indol-6(7H)-ones via a visible light-photocatalyzed formal (4 + 2) cycloaddition of indole-derived bromides and alkenes or alkynes

“…2–9 Therefore, it is not surprising that many efforts have been devoted to the assembly of such useful frameworks. 10–19…”

“…[2][3][4][5][6][7][8][9] Therefore, it is not surprising that many efforts have been devoted to the assembly of such useful frameworks. [10][11][12][13][14][15][16][17][18][19] Recently, the difunctionalization of alkenes has been considered as one of the most powerful methodologies for increasing molecular complexity in synthesis because it can introduce two functional groups across the CvC bond in a single reaction step. [20][21][22][23][24] However, the reaction generally uses Pd, Fe, Rh, Ag, Cu, Au or some organic molecules as catalysts.…”

Recent Advances on the Synthesis of Nine-Membered N-Heterocycles

“…1.1 分子内环化反应构建九元氮杂环化合物 2014 年, Pal 课题组 [15] 在金属钯催化下, 1,2-二取代 吲哚化合物 1 发生分子内 Heck 反应, 选择性通过 9-endo-trig 环化反应合成 1,2-吲哚稠合九元环化合物 2 (Scheme 1). 该方法可以合成许多具有生物活性的稠合 吲哚衍生物, 通过生物活性测试发现, 其中一些合成的 衍生物可以引起斑马鱼胚胎的细胞凋亡.…”