Unexpected One??Step Formation of Iodo [1, 3] dioxolo [4, 5??c] pyridine Derivatives by a Hofmann–Löffler–Freytag Reaction: Studies on the Synthesis of a Pyridine?? …

…, G Podolan, B Brusilowskij, CA Schalley…

Index: Lechel, Tilman; Podolan, Gabriel; Brusilowskij, Boris; Schalley, Christoph A.; Reissig, Hans-Ulrich European Journal of Organic Chemistry, 2012 , # 29 p. 5685 - 5692,8

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Abstract

Abstract During attempts to prepare functionalized 5-iodopyridine derivatives the unexpected formation of iodo [1, 3] dioxolo [4, 5-c] pyridines was discovered. The conversion of 3-alkoxypyridin-4-ols into the corresponding 5-iodo compounds was achieved by reaction with one equivalent of iodine or tetramethylammonium dichloroiodate under basic conditions. When three equivalents of iodine were used in chlorinated solvents, after 5- ...