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Abstract

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Paper | Regular issue | Vol 75, No. 11, 2008, pp. 2667 - 2679
Published online: 3rd July, 2008
DOI: 10.3987/COM-08-11430
Regio- and Stereoselective Synthesis of Thiazole-Substituted Histamine and Adenine Derivatives by Nucleophilic Attack at Allenyl Isothiocyanate

Baker Jawabrah Al-Hourani, Klaus Banert,* Tobias Rüffer, Bernhard Walfort, and Heinrich Lang

*Organic Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111 Chemnitz, Germany

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.

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