Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen

被引：3

作者：

Zasada, Aleksandra ^{[1
,2
]}

Brzeskiewicz, Jakub ^{[1
]}

Antoniak, Damian ^{[1
,3
]}

Bechcicka, Malgorzata ^{[1
]}

Loska, Rafal ^{[1
]}

Makosza, Mieczyslaw ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

[2] Polish Acad Sci, Inst Phys Chem, Kasprzaka 44-52, PL-01224 Warsaw, Poland

[3] Univ Warsaw, Fac Chem, PL-02093 Warsaw, Poland

来源：

ORGANIC & BIOMOLECULAR CHEMISTRY | 2023年 / 21卷 / 05期

关键词：

QUINOLINE N-OXIDES; COPPER-CATALYZED DIRECT; POLYMER SOLAR-CELLS; C-H BOND; ORGANIC-ANIONS; METAL; DESIGN; PHOSPHONATION; CARBANIONS; ALKYLATION;

D O I：

10.1039/d2ob02016e

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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.

引用

页码：994 / 999

页数：6

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