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7
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33748596385
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Gabbutt C.D., Hepworth J.D., Urquhart M.W.J., Vazquez de Miguel L.M. J. Chem. Soc., Perkin Trans. 1. 1997;1819.
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Gabbutt, C.D.1
Hepworth, J.D.2
Urquhart, M.W.J.3
Vazquez de Miguel, L.M.4
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12
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0000169816
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Wipf, P.; Smitrovitch, J. H.; Moon, C.-W. J. Org. Chem. 1992, 57, 3178
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Wipf, P.1
Smitrovitch, J.H.2
Moon, C.-W.3
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13
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0001096579
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Bergdahl, M.; Eriksson, M.; Nilsson, M.; Olsson, T. J. Org. Chem. 1993, 58, 7238;
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, pp. 7238
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Bergdahl, M.1
Eriksson, M.2
Nilsson, M.3
Olsson, T.4
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14
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1542422383
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Eriksson, M.; Ileifski, T.; Nilsson, M.; Olsson, T. J. Org. Chem. 1997, 62, 182.
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Eriksson, M.1
Ileifski, T.2
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Olsson, T.4
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16
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0012980158
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2O at -10 to -15°C for 30-60 min. Cuprates 1a and 1d give colourless to very pale yellow solutions, 1b is orange-yellow, whilst 1c formed a highly insoluble yellow-green solid.
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2O at -10 to -15°C for 30-60 min. Cuprates 1a and 1d give colourless to very pale yellow solutions, 1b is orange-yellow, whilst 1c formed a highly insoluble yellow-green solid.
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18
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0012924865
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note
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3Si requires C, 66.2; H, 5.9%). Similarly, 1c provided 4c as an oil (21%) [bp (Kügelrohr) 155°C/0.15 mbar, mp 111.5-114°C]. Cuprate 1d provided 4d (90%) [bp (Kügelrohr) 150°C/0.1 mbar].
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19
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0012924084
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note
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Cuprate 1b and 2 provided 5Ab directly, after elution from silica (PhMe-EtOAc, 3:7) (50%, mp 158-159°C), whilst the crude product from 2 and 1c (silica, PhMe-EtOAc, 3:7) provided 5Ac (51%, mp 152-156.6°C).
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-
-
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20
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0012967294
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The absence of a cross peak for the alkene proton (δ 6.85) with that for H-2 (δ 6.60) is consistent with the (E) configuration for 5Aa. In 5Ba the (Z) stereochemistry is implicit since the alkene proton is shielded (δ 6.30) and shows a cross peak with the signal for H-2 at 6.10 ppm. The constitution of (Z)-5Ca follows from cross peaks for the -CHO group (δ 9.68) and the alkene proton (δ 6.75).
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The absence of a cross peak for the alkene proton (δ 6.85) with that for H-2 (δ 6.60) is consistent with the (E) configuration for 5Aa. In 5Ba the (Z) stereochemistry is implicit since the alkene proton is shielded (δ 6.30) and shows a cross peak with the signal for H-2 at 6.10 ppm. The constitution of (Z)-5Ca follows from cross peaks for the -CHO group (δ 9.68) and the alkene proton (δ 6.75).
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21
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0013027476
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note
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16 Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number no. CCDC 196356.
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23
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0012925612
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For 3-acetyl-2-methyl-5H-[1]benzopyrano[2,3-b]pyridin-5-one from 3 and acetylacetone, see:
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For 3-acetyl-2-methyl-5H-[1]benzopyrano[2,3-b]pyridin-5-one from 3 and acetylacetone, see: Ghosh C.K. Synth. Commun. 8:1978;487.
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(1978)
Synth. Commun.
, vol.8
, pp. 487
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Ghosh, C.K.1
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24
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18844375618
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For the pentacyclic bisbenzopyranopyridine system from condensation of 3 and chroman-4-ones, see:
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For the pentacyclic bisbenzopyranopyridine system from condensation of 3 and chroman-4-ones, see: Reddy K., Venkat S.G., Rao A.V.S. Org. Prep. Proceed. Int. 28:1996;325.
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(1996)
Org. Prep. Proceed. Int.
, vol.28
, pp. 325
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Reddy, K.1
Venkat, S.G.2
Rao, A.V.S.3
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26
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0037124407
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Daia G.E., Gabbutt C.D., Hepworth J.D., Heron B.M., Hibbs D.E., Hursthouse M.B. Tetrahedron Lett. 43:2002;4507.
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(2002)
Tetrahedron Lett.
, vol.43
, pp. 4507
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Daia, G.E.1
Gabbutt, C.D.2
Hepworth, J.D.3
Heron, B.M.4
Hibbs, D.E.5
Hursthouse, M.B.6
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