Regio- and Stereoselective Synthesis of Thiazole-Substituted Histamine and Adenine Derivatives by Nucleophilic Attack at Allenyl Isothiocyanate

Abstract

The ambident oligonucleophiles histamine and adenine were reacted with allenyl isothiocyanate to yield N-(5-methylthiazol-2-yl) substituted derivatives of the natural products. Whereas histamine led selectively in three clean steps or alternatively in a one-pot procedure to a final product bearing three thiazole units, adenine gave exclusively the mono derivative with a thiazolyl group at N-7. The regio- and stereochemistry of these transformations were proved by single-crystal X-ray analyses of the title compounds.