A One-Pot Direct Iodination of the Fischer–Borsche Ring Using Molecular Iodine and Its Utility in the Synthesis of 6‑Oxygenated Carbazole Alkaloids

Abstract

An efficient regioselective iodination of the Fischer–Borsche ring has been achieved using molecular iodine, in a one-pot synthesis. The acid-, metal-, and oxidant-free conditions of the present method are highly convenient and practical. Furthermore, the one-pot direct iodination process is extended to the concise synthesis of glycozoline, 3-formyl-6-methoxy-carbazole, and 6-methoxy-carbazole-3-methyl­carboxylate natural alkaloids. This method has been proven to be tolerant to a broad range of functional groups, with good to excellent yields