Electron Donor–Acceptor Complex Induced Fused Indoles with Hypervalent Iodine(III) Reagents

Abstract

An operationally simple and efficient method for the cyclization of tertiary amines and hypervalent iodine reagents enabled by an EDA complex has been developed. A series of [1,2-α]indoles derivatives were obtained in good yields, including some key intermediates for the synthesis of biologically active molecules. In addition, this established strategy features a broad substrate scope and good functional group tolerance.

Photoinduced radical tandem annulation of 1,7-diynes: an approach for divergent assembly of functionalized quinolin-2(1H)-ones

“…Aza -heterocyclic compounds are found in a wide variety of natural drugs and biologically active molecules, many of which are pharmacologically important ( Pozharskii et al, 1997 ; Wen et al, 2022 ; Zhao et al, 2023 ; Liu et al, 2023a ; Liu et al, 2023b ). Among these, quinolin-2(1H)-one and its analogs are an important class of nitrogen-containing heterocycle scaffolds and are widely encountered in a myriad of pharmaceutical molecules and synthetic compounds ( Sliskovic et al, 1991 ; Suzuki et al, 2001 ; Bach et al, 2002 ; Kuethe et al, 2005 ) which display versatile biological and pharmacological activities ( McQuaid et al, 1992 ; Michael, 1995 ; Peifer et al, 2008 ), such as P2X7 receptor antagonist, rebamipide, and MAP kinase inhibitor ( Figure 1 ) ( Maignan et al, 2016 ; Tan et al, 2016 ; Miliutina et al, 2017 ; Wu et al, 2020 ).…”

General Synthesis of N-Alkylindoles from N,N-Dialkylanilines via [4 + 1] Annulative Double C–H Functionalization

“…Such an approach would use a (hetero)­aromatic starting material to furnish diverse N -alkylindole frameworks. Very recently, initial efforts targeting this transformation have been reported . The requirement of substrate oxidation significantly limits the scope of these protocols, however, leading to poor regiocontrol with nonsymmetrical substrates and limited functional group tolerance unsuitable for late-stage applications.…”