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Relevant academic research and scientific papers

Synthesis of 2,4-Diarylquinoline Derivatives via Chloranil-Promoted Oxidative Annulation and One-Pot Reaction

An oxidative annulation for the synthesis of 2,4-diarylquinolines from o -allylanilines is disclosed that uses recyclable reagent Chloranil as the oxidant. The corresponding products are obtained in moderate to excellent yields. Furthermore, a one-pot access to 2,4-di aryl quinolines from easily available anilines and 1,3-diarylpropenes is described as a highly atom-efficient protocol that involves oxidative coupling, rearrangement, and oxidative annulation.

Lewis acid catalyzed reactivity switch: Pseudo three-component annulation of nitrosoarenes and (epoxy)styrenes

A Lewis acid catalyzed annulation reaction via arene functionalization of nitrosoarenes and C-C cleavage of (epoxy)styrene to provide arylquinolines is reported. The Lewis acid catalyst altered the annulation pattern providing arylquinolines instead of oxazolidines. The reaction with styrene resulted in a mixture of 2,4-diarylquinoline and 4-Arylquinoline, while only 3-Arylquinoline was formed from the reaction of epoxystyrene. This journal is

Synthesis method of 2, 4-diarylquinoline compound

The invention relates to a synthesis method of a 2, 4-diarylquinoline compound (II), which comprises the following steps: mixing a compound represented by a formula (I), an oxidizing agent and an organic solvent, heating to 60-80 DEG C, reacting for 1-2 hours, and carrying out after-treatment on the reaction solution to obtain a product (II). According to the synthesis method, a metal and other additives are not needed, operation is easy, raw materials are easy to obtain, and conditions are mild.

Silver-catalyzed three-component approach to quinolines starting from anilines, aldehydes, and alcohols

A silver-catalyzed sequential formation of two C-C bonds for the construction of a series of polysubstituted quinolines from anilines, aldehydes, and alcohols under mild conditions has been developed. The transformation is effective for a broad range of substrates, including aliphatic alcohols, arylalkanols, cycloalkanols, and ethylene glycol, thereby permitting the expansion of the constituent architectures of the heterocyclic framework.

Synthesis of polysubstituted quinolines via transition-metal-free oxidative cycloisomerization of o -cinnamylanilines

An efficient synthesis of 2-aryl 4-substituted quinolines from stable and readily available o-cinnamylanilines, prepared from anilines and cinnamylalcohols, has been developed. The reaction occurred via a regioselective 6-endo-trig intramolecular oxidative cyclization using KOtBu as a mediator and DMSO as an oxidant at rt. The reaction showed a broad substrate scope with good to excellent yields.

Silver-mediated C-H activation: Oxidative coupling/cyclization of N -arylimines and alkynes for the synthesis of quinolines

A silver-mediated tandem protocol for the synthesis of quinolines involving the oxidative coupling/cyclization of N-arylimines and alkynes has been developed. We demonstrated that scenario-dependent metalation could occur either at the ortho C-H bond of an N-arylimine through protonation-driven enhancement of acidity or at the terminal C-H bond of an alkyne by virtue of the carbophilic π-acidity of silver. The diverse set of mechanistic manifolds implemented with a single type of experimental protocol points toward the importance of stringent reactivity analysis of each individual potentially reactive molecular site. Importantly, the direct arene C-H bond activation provides a unique and distinct mechanistic handle for the expansion of reactivity paradigms for silver. As expected, the protocol allows for the incorporation of both internal and terminal alkynes into the products, and in addition, both electron-withdrawing and -donating groups are tolerated on N-arylimines, thus enabling the vast expansion of substituent architectures on quinoline framework. Further, an intriguing phenomenon of structural isomerization and chemical bond cleavage has been observed for aliphatic internal alkynes.

Novel Synthesis of 2,4-Diarylquinolines by Photochemical followed by Thermal Transformations of 1,4,6-Triarylpyrimidin-2(1H)-ones

The 2,4-diarylquinolines (3) were obtained in a one-pot synthesis by photochemical and subsequent thermal reactions of 1,4,6-triarylpyrimidin-2(1H)-ones (1) in fair yield.The quinolines (3) were formed via thermal cycloreversion, followed by electrocyclic ring-closure, of the 1,3-diazabicyclohex-5-en-2-ones (2), which were produced by photochemical electrocyclization of the pyrimidin-2(1H)-ones (1).