Recent Advance in Organic Electrochemical Synthesis of Nitrogenous Heterocyclic Compounds Involving Haloids as Mediators

doi:10.6023/cjoc202007049

Abstract

Nitrogenous heterocyclic compounds are widely found in medicinal molecules, natural products and functional materials. Therefore, it has great significance to develop simple and efficient methods for the construction of these compounds. Recently, remarkable progress has been made in haloids mediated electrochemical synthesis of nitrogen heterocycles. Due to the relatively mild reaction condition and environmental protection, it provides a novel approach to construct nitrogen heterocycles. In this review, the recent developments in this area are summarized.

Key words: haloids, electrochemical synthesis, nitrogenous heterocyclic compounds

Cite this article

Yaqin Zhou, Zhiheng Zhao, Liang Zeng, Ming Li, Yonghui He, Lijun Gu. Recent Advance in Organic Electrochemical Synthesis of Nitrogenous Heterocyclic Compounds Involving Haloids as Mediators[J]. Chinese Journal of Organic Chemistry, 2021, 41(3): 1072-1080.

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Fig. & Tab. 24

Scheme 1. Proposed reaction mechanism for electro-catalyzed synthesis of aziridines mediated by iodized salt

Scheme 2. Electrochemical synthesis of aziridines from β-amino ketones

Scheme 3. Electrosynthesis of oxadiazoles

Scheme 4. Electrochemical synthesis of 1,2,4-thiadiazoles

Scheme 5. Proposed reaction mechanism for electro-catalyzed synthesis of 1,2,3-thiadiazoles

Scheme 6. Electrosynthesis of trisubstituted 2-oxazolines

Scheme 7. Electrochemical conversion of CO2 with aryl hydrazines and paraformaldehyde into 1,3,4-oxadiazol-2(3H)-one derivatives

Scheme 8. Multicomponent electro-catalyzed synthesis of 1,5- disubstituted triazoles

Scheme 9. Electro-catalyzed synthesis of substituted imidazoles mediated by iodized salt

Scheme 10. Proposed reaction mechanism for electro-catalyzed synthesis of benzoxazoles mediated by iodized salt

Scheme 11. Electro-catalyzed synthesis of 2-aminobenzoxazoles

Scheme 12. Proposed reaction mechanism for electro-catalyzed synthesis of substituted indoles mediated by iodides

Scheme 13. Electro-catalyzed synthesis of substituted imidazo-fused N-heterocycles

Scheme 14. Electro-catalyzed synthesis of imidazo[1,2-a]pyri- dines

Scheme 15. Electrocatalytic C—H/N—H coupling of 2'-amino- acetophenones for the synthesis of isatins

Scheme 16. Electrochemically catalyzed amino-oxygenation of styrenes for the synthesis of indolines

Scheme 17. Electrochemical catalysis leads to [4+2] annulation for the synthesis of pyrazines

Scheme 18. Electro-catalyzed synthesis of pyrido[1,2-a]-ben- zimidazoles

Scheme 19. Electro-catalyzed synthesis of oxindoles mediated by bromides salt.

Scheme 20. Proposed reaction mechanism for electro-catalyzed trifluoromethylation/cyclization of N-arylacrylamides mediated by bromides salt

Scheme 21. Electro-catalyzed synthesis of pyrrolidines mediated by bromides salt.

Scheme 22. Proposed reaction mechanism for electro-catalyzed synthesis of 1,2,4-triazole[1,5-a]pyridine mediated by bromides salt

Scheme 23. Proposed reaction mechanism for electro-catalyzed synthesis of 5-fluoromethyl-2-azolines mediated by fluorine salt

Scheme 24. Eectro-catalyzed fuorocyclization of N-popargyla- mides

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