Synthesis of azepino[4,5-b]indol-4-ones via MCR/free radical cyclization and in vitro–in silico studies as 5-Ht6R ligands

Construction of Oxepino[3,2‐b]indoles via [4+3] Annulation of 2‐Ylideneoxindoles with Crotonate‐Derived Sulfur Ylides

“…Because of its importance in structure and biological activity, these indole‐fused seven‐membered ring skeletons has drawn tremendous interest from both synthetic and medicinal chemists [1,2] . So far, although various synthetic methods have been developed for the construction of these indole‐fused seven‐membered ring skeletons, [1a,g,2,3] most of these established methods mainly focus on cyclohepta[ b ]indole skeletons [1a,2a–b] and indole‐fused seven‐membered nitrogen‐heterocycle skeletons, [1g,2c–k] but the research on oxepino[3,2‐ b ] indoles are generally lacking (Scheme 1). [3] In recently years, a few synthetic methods like NHC‐catalyzed annulation reaction of indolin‐3‐ones with α,β‐unsaturated aldehydes (Scheme 1a), [3d] visible light catalyzed diastereoselective oxidative C−N/C−O bond formation tandems (Scheme 1b) [3f] and gold‐catalyzed bicyclization of diaryl alkyne (Scheme 1c) [3e] have been developed to construct oxepino[3,2‐ b ] indole skeletons, however, these reported strategies usually require complex reaction system and have limited applications.…”

Synthesis of Polyheterocyclic Dimers Containing Restricted and Constrained Peptidomimetics via IMCR-Based Domino/Double CuAAC Click Strategy

“…Our ongoing research program focuses on the design of new or novel, rapid, convergent, ecofriendly, and efficient post-IMCR/transformation strategies in consecutive [ 32 , 33 , 34 , 35 , 36 , 37 , 38 ] or domino manner [ 39 , 40 , 41 ] toward the synthesis of novel molecules containing conformationally restricted and/or constrained peptidomimetics. Recently, we reported the first ultrasound-assisted green one-pot synthesis of molecules containing privileged restricted peptidomimetics via this strategy: post-IMCR transformation/ Copper(I)-catalyzed azide-alkyne cycloaddition (CuAAC) click reaction employing a green alternative energy source [ 42 ].…”

Synthesis of Tris-Heterocycles via a Cascade IMCR/Aza Diels-Alder + CuAAC Strategy

“…Our ongoing research program focuses on the design of rapid, convergent and efficient IMCR/post-transformation strategies toward novel molecules containing privileged heterocycles: azepino[4,5- b ]indol-4-ones (Rentería-Gómez et al, 2016b), 2-tetrazolylmethyl-isoindolin-1-ones (Rentería-Gómez et al, 2016a), tetrazolo[1,5- a ]quinolines (Unnamatla et al, 2016), 3-tetrazolylmethyl-azepino[4,5- b ]indol-4-ones (Gordillo-Cruz et al, 2013), 2,3,4,9-tetrahydro-1 H -β-carbolines (Cárdenas-Galindo et al, 2014), 4-(pyridine-3-yl)pyrimidines (Cortes-García et al, 2016), and spiro[pyrrolidine-3,3′-oxindoles] (Alvárez-Rodríguez et al, 2018). Herein we describe the first cascade IMCR process/post-transformation strategy toward the synthesis of 4-substituted 1 H -1,2,3-triazoles linked to a fused, bis-heterocyclic peptidomimetic.…”