Cu(II)-Catalyzed [3 + 1 + 1 + 1] Cyclization of 1,3-Diketones and 2‑Naphthols Using N,N‑Dimethylethanolamine as a Dual Carbon Synthon for the Synthesis of 2H‑Chromenes

Reactions with diverse C1 synthons to realize homologation were well explored. However, homologations occurring twice with one C1 synthon in a reaction were less reported. We disclose herein a Cu­(II)-catalyzed novel and efficient synthesis of 2H-chromenes from 2-naphthols, 1,3-diketones, and N,N-di...

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Veröffentlicht in:Journal of organic chemistry 2024-01, Vol.89 (1), p.152-162
Hauptverfasser: Geng, Meiqi, Huang, Minzhao, Kuang, Jinqiang, Fang, Weiwei, Xiao, Xuqiong, Miao, Maozhong, Ma, Yongmin
Format: Artikel
Sprache:eng
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Zusammenfassung:Reactions with diverse C1 synthons to realize homologation were well explored. However, homologations occurring twice with one C1 synthon in a reaction were less reported. We disclose herein a Cu­(II)-catalyzed novel and efficient synthesis of 2H-chromenes from 2-naphthols, 1,3-diketones, and N,N-dimethylethanolamine (DMEA) as a dual carbon synthon. Various 2H-chromenes with different functional groups are constructed in moderate to good yields. This is the first report that DMEA acts as a dual C1 synthon.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.3c01849