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.
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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