Flow electrochemical oxidative cyclisation for the synthesis of heterocyclic compounds

Gieman, Hanaa Hussien M. 2025. Flow electrochemical oxidative cyclisation for the synthesis of heterocyclic compounds. PhD Thesis, Cardiff University. Item availability restricted.

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Abstract

Organic electrochemistry has gained interest among the chemist community due to its unique reactivities that are not achievable through conventional organic synthesis. Electrochemical synthesis offers a green and atom-efficient approach for achieving selective redox transformations by employing electrons as reagents. In electrochemistry, flow microreactors have been used extensively to improve reaction productivity and overcome the limitations commonly associated with batch electrochemical cells. This work outlines the electrosynthesis of heterocyclic compounds using the Ion electrochemical microreactor. In the first part of this thesis, a flow electrochemical method for the synthesis of benzothiadiazine 1,1-dioxides via electrochemical decarboxylative cyclisation of 2- aminobenzenesulfonamide 2.7 and a-keto acids 2.18 has been developed. A broad range of benzothiadiazine 1,1-dioxides was produced in moderate to good yields. An electrolyte-controlled strategy has been developed to precisely govern regioselectivity and reaction outcomes in electrochemical transformation via selective substrate activation using a flow microreactor. A wide variety of substrates with different functional groups were successfully converted to the corresponding isoquinoline N-oxides and isoquinolinium imides in moderate to excellent yields. Finally, an efficient and practical protocol for the synthesis of selenated isocoumarin-1-imine derivatives via an electrochemical oxidative 6-endo-dig-oxo selenocyclisation of o-alkynylbenzamides. Regioselectivity in the reaction is affected by the structural features and electronic properties of the starting materials. A variety of selenated isocoumarin-1-imines products were produced in good to moderate yields under the continuous flow electrochemical reaction conditions.

Item Type:	Thesis (PhD)
Date Type:	Completion
Status:	Unpublished
Schools:	Schools > Chemistry
Date of First Compliant Deposit:	5 December 2025
Last Modified:	05 Dec 2025 16:36
URI:	https://orca.cardiff.ac.uk/id/eprint/182937

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