FeCl3‑Mediated One-Pot Domino Reactions for the Synthesis of 9‑Aryl/9-Arylethynyl-2,3,4,9-tetrahydro‑1H‑xanthen-1-ones from Propargylic Amines/Diaryl Amines and 1,3-Cyclohexanediones

An efficient, environmentally friendly and one-pot route to new 9-aryl/9-arylethynyl-2,3,4,9-tetrahydro-1H-xanthen-1-one derivatives from inexpensive starting materials has been developed. This method proceeded by a domino nucleophilic-substitution/​intramolecular cyclization/​dehydration sequence o...

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Veröffentlicht in:Journal of organic chemistry 2016-03, Vol.81 (5), p.2062-2069
Hauptverfasser: He, Xinwei, Tao, Jiajia, Hu, Xiaoqian, Wang, Hui, Shang, Yongjia
Format: Artikel
Sprache:eng
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Zusammenfassung:An efficient, environmentally friendly and one-pot route to new 9-aryl/9-arylethynyl-2,3,4,9-tetrahydro-1H-xanthen-1-one derivatives from inexpensive starting materials has been developed. This method proceeded by a domino nucleophilic-substitution/​intramolecular cyclization/​dehydration sequence of propargylic amines/diaryl amines and 1,3-cyclohexanediones under the promotion of FeCl3, which involved the formation of two new σ (C–C and C–O) bonds in a single operation for the construction of novel tetrahydroxanthene skeletons in 68–95% yields.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.6b00001