Iridium-catalyzed selective hydrogenation of 3-hydroxypyridinium salts: A facile synthesis of piperidin-3-ones
The selective hydrogenation of 3-hydroxypyridinium salts has been achieved using a homogeneous iridium catalyst, providing a direct access to 2- and 4-substituted piperidin-3-one derivatives with high yields, which are important organic synthetic intermediates and the prevalent structural motifs in pharmaceutical agents. Mild reaction conditions, high chemoselectivity, and easy scalability make this reaction highly practical for the synthesis of piperidin-3-ones.
Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin
Selenium dioxide-mediated methoxyhydroxylation of cyclic arylolefin with the modest yields is described. This facile strategy was also used to synthesize several 4-arylpyridines, 3-hydroxy-4-arylpyridines, and 3,4-diarylpyridines. Crown Copyright
Chang, Meng-Yang,Lin, Chung-Han,Chen, Yeh-Long
scheme or table
p. 1430 - 1433
(2010/05/03)
Synthesis of 3-hydroxypyridines using ruthenium-catalyzed ring-closing olefin metathesis
(Chemical Equation Presented) New synthetic routes to substituted 3-hydroxypyridines 6 are presented. Ring-closing olefin metathesis (RCM)/elimination and RCM/oxidation/ deprotection of nitrogen-containing dienes 4 are the key processes of the routes. An
Dipolar cycloaddition route to diverse analogues of cocaine: The 6- and 7-substituted 3-phenyltropanes
In our quest for an antagonist or partial agonist of cocaine, access to certain 6- and 7-substituted 3-phenyltropanes of type I was required. Starting from 3-hydroxy-1-methyl-4-phenylpyridinium iodide, we disclose a pyridinium betaine-based dipolar cycloaddition route to tropenones of type II. In turn, we show how this intermediate can be transformed to type I products either through the copper-catalyzed conjugate addition reaction of Grignard reagents to the enones 7-9 or by the copper(I)-catalyzed cross coupling reaction of the allylic acetates 15a and 16a with Grignard reagents.
Kozikowski, Alan P.,Araldi, Gian Luca,Ball, Richard G.
p. 503 - 509
(2007/10/03)
Synthesis of 4-Alkyl-3-pyridinols from 3-Benzyloxypyridine
The addition of Grignard reagents to the 1-phenoxycarbonyl salt of 3-benzyloxypyridine and a catalytic amount of cuprous iodide afforded 4-alkyl-3-benzyloxy-1-phenoxycarbonyl-1,4-dihydropyridines in good yield.The crude dihydropyridines were aromatized wi
Comins, Daniel L.,Stroud, Eric D.
p. 1419 - 1420
(2007/10/02)
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