Identification of a Novel 1,4,8-Triazaphenanthrene Derivative as a Neuroprotectant for Dopamine Neurons Vulnerable in Parkinson’s Disease

An efficient and metal-free double CÀH bond amination of N-aryl enamines using isobutyl nitrite (IBN) has been developed. This method enables the preparation of functionalized quinoxalines in good to excellent yields and tolerates a variety of N-aryl enamines with diverse functional substituents. Mechanistic studies revealed the presence of a key b-imino oxime ester intermediate. A quinoxaline derivative could be prepared from bcarbonyl ester in one-pot sequence on a gram scale. Finally, two important quinoxaline scaffolds were easily prepared in moderate yields over two steps.

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Isobutyl Nitrite‐Mediated Synthesis of Quinoxalines through Double C−H Bond Amination of N‐Aryl Enamines

Jiao

Wei

Zhao

et al. 2018

Adv Synth Catal

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Iridium‐Catalyzed [4+2] Annulations of β‐Keto Sulfoxonium Ylides and o‐Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives

et al. 2020

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A synthetic method for quinoxaline derivatives from the [4+2] annulation of β‐keto sulfoxonium ylides and o‐phenylenediamine by using (Cp*IrCl2)2 catalyst is described. This novel protocol features mild reaction conditions, moderate to excellent yields, wide substrate scope, and high functional‐group compatibility. Moreover, this cyclization strategy was successfully applied in late‐stage modification for structurally complex bioactive compounds.

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Rh(III)‐Catalyzed Oxidative Annulation of 2‐Arylquinoxalines with Cyclic 2‐Diazo‐1,3‐diketones by C−H Bond Activation

et al. 2023

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Rh(III)-catalyzed CÀ H bond annulation of 2-arylquinoxalines with cyclic 2-diazo-1,3-diketones has been accomplished for the first time to synthesize a novel series of 2,3dihydrodibenzo[a,c]phenazin-4(1H)-one frameworks by means of carbene insertion followed by condensation. The reaction proceeds through the CÀ H bond activation and functionalization of 2-arylquinoxalines using Rh(III)/AgSbF 6 complex to produce highly substituted 2,3-dihydrodibenzo[a,c]phenazin-4(1H)-one and benzo [5,6][1,2,4]thiadiazino[2,3-f]phenanthridin-5(6H)-one-10,10-dioxide derivatives in good to excellent yields.

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Identification of a Novel 1,4,8-Triazaphenanthrene Derivative as a Neuroprotectant for Dopamine Neurons Vulnerable in Parkinson’s Disease

Cited by 4 publications

References 31 publications

Isobutyl Nitrite‐Mediated Synthesis of Quinoxalines through Double C−H Bond Amination of N‐Aryl Enamines

Isobutyl Nitrite‐Mediated Synthesis of Quinoxalines through Double C−H Bond Amination of N‐Aryl Enamines

Iridium‐Catalyzed [4+2] Annulations of β‐Keto Sulfoxonium Ylides and o‐Phenylenediamines: Mild and Facile Synthesis of Quinoxaline Derivatives

Rh(III)‐Catalyzed Oxidative Annulation of 2‐Arylquinoxalines with Cyclic 2‐Diazo‐1,3‐diketones by C−H Bond Activation

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