A New Synthesis of 2,3-Dihydrobenzo[1,4]dioxine and 3,4-Dihydro-2H-benzo[1,4]oxazine Derivatives by Tandem Palladium-Catalyzed Oxidative Aminocarbonylation−Cyclization of 2-Prop-2-ynyloxyphenols and 2-Prop-2-ynyloxyanilines

2006 ◽  
Vol 71 (20) ◽  
pp. 7895-7898 ◽  
Author(s):  
Bartolo Gabriele ◽  
Giuseppe Salerno ◽  
Lucia Veltri ◽  
Raffaella Mancuso ◽  
Zhiyu Li ◽  
...  
Keyword(s):  
New Synthesis ◽  
Palladium Catalyzed ◽  
Oxazine Derivatives

ChemInform Abstract: A NEW SYNTHESIS OF BICYCLO(1,3)OXAZINE DERIVATIVES

1981 ◽  
Vol 12 (1) ◽  
Author(s):  
M. OKITA ◽  
T. WAKAMATSU ◽  
M. MORI ◽  
Y. BAN
Keyword(s):  
New Synthesis ◽  
Oxazine Derivatives

scholarly journals 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

2016 ◽  
Vol 12 ◽  
pp. 2898-2905 ◽  
Author(s):  
Michal Medvecký ◽  
Igor Linder ◽  
Luise Schefzig ◽  
Hans-Ulrich Reissig ◽  
Reinhold Zimmer
Keyword(s):  
Click Reaction ◽  
Cross Coupling ◽  
Coupling Reactions ◽  
High Efficacy ◽  
Carbon Bond ◽  
Bond Forming ◽  
Cross Coupling Reactions ◽  
Carbon Carbon Bond ◽  
Palladium Catalyzed ◽  
Oxazine Derivatives

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.

ChemInform Abstract: A NEW SYNTHESIS OF ANTHRAMYCIN VIA PALLADIUM-CATALYZED CARBONYLATION

1982 ◽  
Vol 13 (46) ◽  
Author(s):  
M. ISHIKURA ◽  
M. MORI ◽  
M. TERASHIMA ◽  
Y. BAN
Keyword(s):  
New Synthesis ◽  
Palladium Catalyzed
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