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
| Autor: | Luise Schefzig, Hans-Ulrich Reissig, Michal Medvecký, Reinhold Zimmer, Igor Linder |
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| Rok vydání: | 2016 |
| Předmět: |
Sonogashira coupling
Oxazines Cyanation 010402 general chemistry 01 natural sciences Coupling reaction lcsh:QD241-441 cross-coupling reactions lcsh:Organic chemistry Suzuki reaction iodination Moiety Organic chemistry lcsh:Science chemistry.chemical_classification 010405 organic chemistry Organic Chemistry amino alcohol Halogenation 1 2-oxazines 0104 chemical sciences chemistry Click chemistry lcsh:Q hydrogenation click reaction |
| Zdroj: | Beilstein Journal of Organic Chemistry, Vol 12, Iss 1, Pp 2898-2905 (2016) |
| ISSN: | 1860-5397 |
| DOI: | 10.3762/bjoc.12.289 |
| Popis: | Iodination of carbohydrate-derived 3,6-dihydro-2H-1,2-oxazines of type 3 using iodine and pyridine in DMF furnished 5-iodo-substituted 1,2-oxazine derivatives 4 with high efficacy. The alkenyl iodide moiety of 1,2-oxazine derivatives syn-4 and anti-4 was subsequently exploited for the introduction of new functionalities at the C-5 position by applying palladium-catalyzed carbon–carbon bond-forming reactions such as Sonogashira, Heck, or Suzuki coupling reactions as well as a cyanation reaction. These cross-coupling reactions led to a series of 5-alkynyl-, 5-alkenyl-, 5-aryl- and 5-cyano-substituted 1,2-oxazine derivatives being of considerable interest for further synthetic elaborations. This was exemplarily demonstrated by the hydrogenation of syn-21 and anti-24 and by a click reaction of a 5-alkynyl-substituted precursor. |
| Databáze: | OpenAIRE |
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