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2 article(s) from Linder, Igor

Iodination of carbohydrate-derived 1,2-oxazines to enantiopure 5-iodo-3,6-dihydro-2H-1,2-oxazines and subsequent palladium-catalyzed cross-coupling reactions

Michal Medvecký,
Igor Linder,
Luise Schefzig,
Hans-Ulrich Reissig and
Reinhold Zimmer

Beilstein J. Org. Chem. 2016, 12, 2898–2905, doi:10.3762/bjoc.12.289

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Graphical Abstract

Scheme 1: Access to enantiopure 3,6-dihydro-1,2-oxazines 3 via lithiated alkoxyallenes 1 and carbohydrate-der...

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Scheme 2: Iodination of 1,2-oxazines syn-3a–c and anti-3a,d leading to 5-iodo-substituted 1,2-oxazines syn-4a...

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Scheme 3: Sonogashira reactions of 4-methoxy-1,2-oxazines syn-4a, anti-4a and anti-4d leading to 5-alkynyl-su...

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Scheme 4: Sonogashira reactions of D-glyceraldehyde-derived 1,2-oxazines syn-4a–c leading to 5-alkynyl-substi...

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Scheme 5: Heck reactions of 1,2-oxazine syn-4a leading to 5-alkenyl-substituted 1,2-oxazines syn-13, syn-14 a...

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Scheme 6: Suzuki–Miyaura reactions of 1,2-oxazines syn-4a, syn-4b and anti-4d leading to 5-styryl-substituted...

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Scheme 7: Cross-coupling reaction of 1,2-oxazine anti-4d leading to 5-cyano-substituted 1,2-oxazine anti-25.

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Scheme 8: Desilylation of 1,2-oxazine syn-5 and subsequent click reaction with benzyl azide leading to 5-(1,2...

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Scheme 9: Hydrogenation of 1,2-oxazine syn-21 leading to γ-amino alcohols 27a,b and subsequent ring closure t...

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Scheme 10: Hydrogenation of 1,2-oxazine anti-24 to products anti-29 and anti-30.

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Full Research Paper

Published 29 Dec 2016

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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.

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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.

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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 ...

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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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