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Synthesis 1989; 1989(12): 968-970
DOI: 10.1055/s-1989-27452
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Ring Transformations via Bridged 1,3-Dicarbonyl Heteroanalogs; Part II.1. Synthesis of 4-(ω-Aminoalkyl)-thiazoles by a Novel Ring Transformation Reaction of Semicyclic Thioacylamidines with Acidic Methyl Halides

Jürgen Liebscher* , Michael Pätzel, Ute Bechstein
  • *Sektion Chemie, Humboldt-Universität Berlin, Hessische Straße 1 2, DDR-1040 Berlin, German Democratic Republic
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Publication Date:
02 May 2002 (online)

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Semicyclic N′-(thioacyl)amidines 1 react with acidic methyl halides 2 as C-synthons via S-alkylation and cyclization to give 4-(ω-aminoalkyl)-thiazole hydrohalides 5. In this transformation, the thiazole ring is formed while the initial lactam ring is opened. In contrast, semicyclic N-(thioacyl)amidines 1 react with α-haloketones as C-C building blocks in a Hantzsch-type thiazole synthesis affording semicyclic 2-amidinothiazoles 6 or thiazolium salt 7 while the starting lactamimine ring is retained.