Competitive intramolecular C-C vs. C-O bond coupling reactions toward C6 ring-fused 2-pyridone synthesisElectronic supplementary information (ESI) available: Experimental data and copies of 1H and 13C NMR spectra of the starting materials, arylated and aryloxylated products. See DOI: 10.1039/c6ob00303f
An interesting competitive C-C vs . C-O bond coupling reaction on N ,3,5-trisubstituted pyridones is reported. These coupling reactions provided selective access to C- or O-ring-fused pyridones, both at the challenging C 6 -pyridone position. 1,6- C -Annulated pyridones were generally achieved in go...
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Main Authors | , , , , , , |
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Format | Journal Article |
Published |
30.03.2016
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Online Access | Get full text |
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Summary: | An interesting competitive C-C
vs
. C-O bond coupling reaction on
N
,3,5-trisubstituted pyridones is reported. These coupling reactions provided selective access to C- or O-ring-fused pyridones, both at the challenging C
6
-pyridone position. 1,6-
C
-Annulated pyridones were generally achieved in good yields with excellent chemoselectivity under Pd(0) conditions. On the other hand, full C
6
-regioselective Csp
2
aryloxylation was achieved under oxidative coupling promoted by silver salts to access 5,6-
O
-annulated pyridones. Based on various experiments and observations, mechanistic evidence of these competitive reactions was provided and it was proposed that C-O bond formation proceeded through radical cyclization. These processes were performed under mild reaction conditions and offer an efficient and attractive methodology to selectively access a large scope of
C
-arylated and
O
-arylated pyridones of biological interest.
This work described a competitive C-C
vs.
C-O bond forming reaction at the challenging C
6
-position of 2-pyridones through Pd catalysis and silver radical cyclization. |
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Bibliography: | 1 13 10.1039/c6ob00303f Electronic supplementary information (ESI) available: Experimental data and copies of H and C NMR spectra of the starting materials, arylated and aryloxylated products. See DOI |
ISSN: | 1477-0520 1477-0539 |
DOI: | 10.1039/c6ob00303f |