volume 21 issue 5 pages 994-999

Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen

Publication typeJournal Article
Publication date2023-01-01
scimago Q2
wos Q2
SJR0.600
CiteScore5.2
Impact factor2.7
ISSN14770520, 14770539
PubMed ID:  36515404
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
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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Zasada A. et al. Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 5. pp. 994-999.
GOST all authors (up to 50) Copy
Zasada A., Brześkiewicz J., Antoniak D., Bechcicka M., Loska R., Mąkosza M. Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen // Organic and Biomolecular Chemistry. 2023. Vol. 21. No. 5. pp. 994-999.
RIS |
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RIS Copy
TY - JOUR
DO - 10.1039/d2ob02016e
UR - https://xlink.rsc.org/?DOI=D2OB02016E
TI - Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen
T2 - Organic and Biomolecular Chemistry
AU - Zasada, Aleksandra
AU - Brześkiewicz, Jakub
AU - Antoniak, Damian
AU - Bechcicka, Małgorzata
AU - Loska, Rafał
AU - Mąkosza, Mieczysław
PY - 2023
DA - 2023/01/01
PB - Royal Society of Chemistry (RSC)
SP - 994-999
IS - 5
VL - 21
PMID - 36515404
SN - 1477-0520
SN - 1477-0539
ER -
BibTex |
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BibTex (up to 50 authors) Copy
@article{2023_Zasada,
author = {Aleksandra Zasada and Jakub Brześkiewicz and Damian Antoniak and Małgorzata Bechcicka and Rafał Loska and Mieczysław Mąkosza},
title = {Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen},
journal = {Organic and Biomolecular Chemistry},
year = {2023},
volume = {21},
publisher = {Royal Society of Chemistry (RSC)},
month = {jan},
url = {https://xlink.rsc.org/?DOI=D2OB02016E},
number = {5},
pages = {994--999},
doi = {10.1039/d2ob02016e}
}
MLA
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MLA Copy
Zasada, Aleksandra, et al. “Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen.” Organic and Biomolecular Chemistry, vol. 21, no. 5, Jan. 2023, pp. 994-999. https://xlink.rsc.org/?DOI=D2OB02016E.
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