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 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.6b00001 |