Electrochemical oxidative dehydrogenative annulation of 1-(2-aminophenyl)pyrroles with cleavage of ethers to synthesize pyrrolo[1,2-<i>a</i>]quinoxaline derivatives

Sun, Fengkai; Miao, Man; Li, Wenxue; Lan, Xiao-Bing; Yu, Jian-Qiang; Zhang, Jian; An, Zhenyu

doi:10.1039/d3ob01867a

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01867a

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Electrochemical oxidative dehydrogenative annulation of 1-(2-aminophenyl)pyrroles with cleavage of ethers to synthesize pyrrolo[1,2-a]quinoxaline derivatives

Fengkai Sun,

Man Miao,

Wenxue Li

et al.

Abstract: In this study, we present an electrochemical approach for the synthesis of pyrrolo[1,2-a]quinoxaline derivatives from 1-(2-aminophenyl)pyrroles and ethers in simple homemade undivided cells.

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Cited by 4 publications

References 39 publications

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Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Sun,

Miao,

et al. 2024

Adv Synth Catal

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A direct electrochemical redox reaction involving radical cross‐coupling cyclization for the synthesis of pyrrolo[1,2‐a]quinoxaline derivatives from 1‐(2‐aminophenyl)pyrroles and CH3CN has been developed, which includes the functionalization of C(sp3)‐H bonds as well as the construction of C‐C and C‐N bonds. Notably, the control and deuterium‐labelling experiments suggest that CH3CN in this reaction acts as both a carbon source via C‐C cleavage and solvent. The reaction features metal‐ and oxidant‐free conditions, and various substituted pyrrolo[1,2‐a]quinoxaline derivatives were obtained.

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Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Sun,

Miao,

et al. 2024

Adv Synth Catal

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Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

Grishin,

Mulina,

et al. 2024

Asian J Org Chem

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The use of C‐H compounds as reactive partners in a variety of transformations represents the state of the art in synthetic methodology. In this review, we have summarized the main achievements in using ethers as building blocks for the construction and modification of one of the basic platforms of organic chemistry, nitrogen‐containing heterocycles. Ethers, previously considered mainly as solvents, are excellent CH‐partners, capable of generating radical or cationic reactive species under the action of HAT agents and oxidants. The challenge in this field is the still limited number of heterocyclic systems and other starting reagents, with which the processes can be carried out selectively due to closer bond dissociation energies and oxidation potentials of heterocycles, reactive intermediates and ethers. However, the fine‐tuning of the reaction system using electro‐ and photochemical approaches and a deep understanding of the reaction pathways make the use of ethers as C‐H reagents a promising synthetic strategy.

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A General Method for Elemental Sulfur Promoted Synthesis of Ortho‐Substituted Pyrrolo[1,2‐a]quinoxalin‐4‐yl Anilines

Ho,

Ngo,

Nguyen

2024

ChemistrySelect

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Synthesis of heteroaryl ortho‐substituted anilines is hitherto challenging. Herein we report scope and limitation of method for annulation of 1‐(2‐nitroaryl)pyrroles and derivatives of 2‐aminobenzyl alcohol to afford ortho‐substituted pyrrolo[1,2‐a]quinoxalin‐4‐yl anilines. Reaction conditions contained elemental sulfur as promoter, while were tolerant of a wide range of aryl and heteroaryl amines. Our method would offer a feasible tactic to yield anilines steric bulk with ortho heterocyclic substituents.

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Electrochemical oxidative dehydrogenative annulation of 1-(2-aminophenyl)pyrroles with cleavage of ethers to synthesize pyrrolo[1,2-a]quinoxaline derivatives

Abstract: In this study, we present an electrochemical approach for the synthesis of pyrrolo[1,2-a]quinoxaline derivatives from 1-(2-aminophenyl)pyrroles and ethers in simple homemade undivided cells.

Cited by 4 publications

References 39 publications

Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

A General Method for Elemental Sulfur Promoted Synthesis of Ortho‐Substituted Pyrrolo[1,2‐a]quinoxalin‐4‐yl Anilines

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Electrochemical oxidative dehydrogenative annulation of 1-(2-aminophenyl)pyrroles with cleavage of ethers to synthesize pyrrolo[1,2-a]quinoxaline derivatives

Abstract: In this study, we present an electrochemical approach for the synthesis of pyrrolo[1,2-a]quinoxaline derivatives from 1-(2-aminophenyl)pyrroles and ethers in simple homemade undivided cells.

Cited by 4 publications

References 39 publications

Direct C−C Bond Cleavage of CH3CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Direct C−C Bond Cleavage of CH3CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Ethers as Building Blocks for the Synthesis and Modification of N‐Heterocycles

A General Method for Elemental Sulfur Promoted Synthesis of Ortho‐Substituted Pyrrolo[1,2‐a]quinoxalin‐4‐yl Anilines

Contact Info

Product

Resources

About

Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation

Direct C−C Bond Cleavage of CH₃CN as a Single‐Carbon Synthon: Synthesis of Pyrrolo[1,2‐a]quinoxalines via Electrochemical Oxidation