Radical Addition of 4-Hydroxyquinazolines and Alkylation of Quinones by the Electro-Induced Homolysis of 4-Alkyl-1,4-di­hydropyridines

Abstract The formation of C(sp 3 )-centered radicals via the electro-­induced homolysis of 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) is reported. The resulting alkyl radicals reacted with 4-hydroxyquinazolines or quinones to afford 2-alkyldihydroquinazolinones or alkylated quinones. A broad range of...

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Veröffentlicht in:Synthesis (Stuttgart) 2022-06, Vol.54 (11), p.2696-2706
Hauptverfasser: Luo, Xiaosheng, Feng, Qiping, Wang, Ping
Format: Artikel
Sprache:eng
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Zusammenfassung:Abstract The formation of C(sp 3 )-centered radicals via the electro-­induced homolysis of 4-alkyl-1,4-dihydropyridines (alkyl-DHPs) is reported. The resulting alkyl radicals reacted with 4-hydroxyquinazolines or quinones to afford 2-alkyldihydroquinazolinones or alkylated quinones. A broad range of alkyl DHPs could be used as versatile radical precursors under electrolysis conditions. This alterative strategy provided a simple and effective pathway for the construction of C(sp 2 )–C(sp 3 ) and C(sp 3 )–C(sp 3 ) bonds under mild conditions.
ISSN:0039-7881
1437-210X
DOI:10.1055/a-1737-2765