p -TsOH promoted synthesis of benzo-fused O-heterocycles from alkynols via ring contraction and C–O scission strategy
Here, we report the first divergent synthesis of benzo-fused O-heterocycles by p -toluene sulfonic acid promoted cascade reactions involving alkyne hydration, double cyclization, ring contraction and C–O bond cleavage from alkynols. The reaction mechanism was validated by obtaining the X-ray structu...
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Veröffentlicht in: | Green chemistry : an international journal and green chemistry resource : GC 2018, Vol.20 (15), p.3420-3425 |
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Hauptverfasser: | , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | Here, we report the first divergent synthesis of benzo-fused O-heterocycles by
p
-toluene sulfonic acid promoted cascade reactions involving alkyne hydration, double cyclization, ring contraction and C–O bond cleavage from alkynols. The reaction mechanism was validated by obtaining the X-ray structure of fused benzo[
b
]oxepine intermediates. Moreover, some of the obtained derivatives could be transformed into 2,3-disubstituted naphthoquinones as important structural motifs in natural products and bioactive molecules. |
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ISSN: | 1463-9262 1463-9270 |
DOI: | 10.1039/C8GC00749G |