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1 article(s) from Duhs, Marcel-Antoine

Palladium- catalyzed cross coupling reactions of 4-bromo- 6H-1,2-oxazines

Reinhold Zimmer,
Elmar Schmidt,
Michal Andrä,
Marcel-Antoine Duhs,
Igor Linder and
Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2009, 5, No. 44, doi:10.3762/bjoc.5.44

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Graphical Abstract

Scheme 1: Brominations of 6H-1,2-oxazines. a) Br₂, Et₂O, −30 °C, 2 h. b) Et₃N, −30 °C to r.t., overnight.

Jump to Scheme 1

Scheme 2: Chlorinations of 6H-1,2-oxazines. a) Cl₂, Et₂O, −30 °C. b) Et₃N, −30 °C to r.t.

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Scheme 3: Suzuki-couplings of 4-bromo-6H-1,2-oxazines. a) ArB(OH)₂, Pd(PPh₃)₄, Na₂CO₃, toluene, 80 °C, 3 h.

Jump to Scheme 3

Scheme 4: Sonogashira-couplings of 4-bromo-6H-1,2-oxazines. a) PdCl₂(PPh₃)₂, CuI, Et₃N, toluene, r.t., 6–20 h....

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Scheme 5: Sonogashira-couplings of 4,5-dibromo-6H-1,2-oxazines. a) PdCl₂(PPh₃)₂, CuI, Et₃N, toluene, r.t., 4 ...

Jump to Scheme 5

Scheme 6: Preparation of trisubstituted pyridine derivatives: a) BF₃·OEt₂, CH₂Cl₂, −78 °C to r.t., overnight.

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Preliminary Communication

Published 16 Sep 2009

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