Catalytic formal [4 + 1] isocyanide-based cycloaddition: an efficient strategy for the synthesis of 1H-cyclopenta[b]quinolin-1-one derivatives

Abstract

Herein we describe an unprecedented isocyanide-based cycloaddition of alkyl and aryl isocyanides with (Z)-2-(2-hydroxy-2-alkylvinyl)quinoline-3-carbaldehydes. On the basis of DFT calculations a mechanism is proposed.

Sequential Base‐Promoted Formal [4+2] Allenoate Based Cycloaddition: Synthesis of Functionalized Acridines

“…www.eurjoc.org Recently, our group has reported an unprecedented formal [4 + 1] isocyanide-based cycloaddition of (Z)-2-(2-hydroxy-2alkylvinyl) quinoline-3-carbaldehydes by using InCl 3 as the catalyst for the synthesis of 1H-cyclopenta[b]quinolin-1-ones (Scheme 1d). [15] As a partner in formal [4 + 2] cycloaddition reaction of allenoates, (Z)-2-(2-hydroxy-2-alkylvinyl) quinoline-3-carbaldehydes were selected as the four carbon sources to participitate in the [4 + 2] cycloaddition reactions.…”

“…Recently, our group has reported an unprecedented formal [4+1] isocyanide‐based cycloaddition of ( Z )‐2‐(2‐hydroxy‐2‐alkylvinyl) quinoline‐3‐carbaldehydes by using InCl 3 as the catalyst for the synthesis of 1 H ‐cyclopenta[ b ]quinolin‐1‐ones (Scheme 1d) [15] …”

Regio- and diastereoselective transition metal-free hydroalkylation of N-allenyl sulfonamides by push–pull 2-alkynylquinolines

“…Recently our group reported the ( Z )-2-(2-hydroxy-2-alkylvinyl) quinoline-3-carbaldehyde as a type of quinoline skeletons which used in [4 + 1] cycloaddition reaction. 17 This structure can be considered a push–pull 2-alkynylquinoline that quinoline and enole segments act as an electron-withdrawing group and electron-donating group, respectively. From this viewpoint, push–pull 2-alkynylquinoline can be introduced as a novel form of efficient CH acid instead of prevalent CH acids like dicarbonyls compounds.…”

Synthesis, Biological Evaluation and Molecular Docking of Deferasirox and Substituted 1,2,4‐Triazole Derivatives as Novel Potent Urease Inhibitors: Proposing Repositioning Candidate

“…These observations stimulated our interest to study the urease inhibitory activity of the DFX and some of its new derivatives for the first time and investigate the role of OH and various substituted 1,2,4‐triazole groups in the inhibition of urease activity. In this regard and continuation of our research interest in the synthesis of heterocyclic skeletons, we report an efficient procedure for the synthesis of some DFX analogs ( N ‐substituted bis‐hydroxyphenyl‐1,2,4‐triazoles), containing triazole backbone ( Scheme ). The present article, therefore, describes urease inhibitory properties of newly synthesized compounds and investigates their mode of molecular interaction to reveal the probable mechanism class of these compounds, including complexation of nickel ions, blocking the active channel site, or the possibility of covalent interaction with a cysteine residue.…”