Supramolecular Ensemble of Tetraphenylcyclopentadienone Derivative and HgO nanoparticles: A One-Pot Approach for the Synthesis of Quinoline and Quinolone Derivatives

Abstract

Electron deficient tetraphenylcyclopentadienone appended with thiophene has been designed and synthesized which exihibits aggregation induced emission enhancement (AIEE) to form fluorescent assemblies in aqueous media. These emissive aggregates exhibit mercury induced emission enhancement in aqueous media and serve as reactors for the generation of mercury oxide nanoparticles. Further, the in situ generated supramolecular ensemble of tetraphenylcyclopentadienone aggregates and HgO nanomaterial show high catalytic efficiency in the reactions for the synthesis of N-heterocyclic derivatives through ortho CÀH functionalization of unprotected anilines. In addition, this catalytic system has been utilized for the kynurenic acid methyl esters (KYNA methyl ester) derivatives based non-steroidal anti-inflammatory drug through CÀH functionalization strategy which is unprecedented in the literature [a] M.

2‐(Alkynyl)anilines and Derivatives — Versatile Reagents for Heterocyclic Synthesis

“…When 2‐aminophenylpropiolates (R 2 =CO 2 Alk) were treated with arylboronic acids under Cu‐catalysis, quinolone formation was achieved [124] . The in situ formation of an ynoate was also documented in a C−H activation process [125] . Transformations of ynones into quinolones 119 – 121 can be achieved under the action of various coupling partners – sulfinates, nitrite, DMF as a source of NHMe 2 , [126] DMF as a source of both NHMe 2 and CH, [127] and azides [128] .…”

Metal Nanoparticle‐Catalyzed Alkyne Cyclization for the Synthesis of Heterocycles

“…The HgO NPs showed high catalytic activity in the reaction of unprotected anilines, aldehydes and terminal alkynes for the synthesis of quinoline derivatives, which undergoes imine formation, ortho C( sp 2 )−H activation, Sonogashira coupling and an intramolecular cyclization process (Scheme 68). [79] The transformation of unprotected anilines, CO and terminal alkynes could be conducted by using HgO NPs for the construction of kynurenic acid methyl esters, through a cascade of ortho C( sp 2 )−H activation, CO insertion, Sonogashira coupling and intramolecular cyclization (Scheme 69). This catalyst could be reused up to three times.…”

A decennary update on applications of metal nanoparticles (MNPs) in the synthesis of nitrogen- and oxygen-containing heterocyclic scaffolds

“…A supramolecular assembly of tetraphenylcyclopentandienone with HgO NPs was reported for the synthesis of quinolines (116j) using benzaldehydes (21d), anilines (6f) and acetylene carboxylates (48f) (Scheme 235). 416 This protocol was also extended for the synthesis of quinolones via C-H activation, which was used in synthesis of anti-inammatory kynurenic acid methyl esters. The catalyst was recycled and reused up to three times without appreciable loss in its activity.…”