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Synthesis 1995; 1995(8): 879-894
DOI: 10.1055/s-1995-4432
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Ring Transformation Reactions of Bridged 1,3-Dicarbonyl Heteroanalogs as a Versatile Entry to Side Chain Functionalized Alkylheterocycles

Michael Pätzel, Jürgen Liebscher*
  • *Institut für Chemie, Humboldt Universität zu Berlin, Hessische Str. 1-2, D-10115 Berlin, Germany, Fax +49(30)28468343; E-mail liebscher@chemie.hu-berlin.de
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Publication Date:
31 December 2000 (online)

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Cyclic 1,3-dicarbonyl heteroanalogs and their 2-aza-derivatives with one heteroatom being connected to 1-, 2-, or 3-position via an alkyl or heteroalkyl bridge can react with bifunctional reagents by a special type of ring transformation. In this process a heterocycle is formed while the substitution of the bridged heteroatom causes cleavage of the starting ring giving an ω-functionalized alkyl chain. Thus, this ring transformation opens up a convenient and versatile access to ω-functionalized alkylheterocycles.

Ring transformations of bridged 1,3-dicarbonylheteroanalogs afford ω-aminoalkyl-, ω-hydroxyalkyl- and ω-mercaptoalkylheterocycles.

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