Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen?
Organic & Biomolecular Chemistry Pub Date: 2022-12-08 DOI: 10.1039/D2OB02016E
Abstract
The electrophilic nature of quinoxaline has been explored in the vicarious nucleophilic substitution (VNS) of hydrogen with various carbanions as nucleophiles in an attempt to develop a general method for functionalizing the heterocyclic ring. Only poorly stabilized nitrile carbanions were found to give the VNS products. 2-Chloroquinoxaline gave products of SNAr of chlorine preferentially. A variety of quinoxaline derivatives containing cyanoalkyl, sulfonylalkyl, benzyl or ester substituents, including fluorinated ones, have been prepared in the VNS reactions with quinoxaline N-oxide.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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