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Synthesis 1987; 1987(5): 460-466
DOI: 10.1055/s-1987-33425
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Cyclic Guanidines; I. Intramolecular Mercury(II)-Induced Amination of Alkenes as a Convenient Route to Bicyclic Guanidines

Franz Esser*
  • *Department of Medicinal Chemistry, Boehringer Ingelheim KG D-6507 Ingelheim am Rhein, West Germany
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Publikationsdatum:
18. September 2002 (online)

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A convenient route to bicyclic guanidines is reported starting from alkenylated monocyclic guanidines, which undergo intramolecular addition via aminomercuration. The dependence of the regioselectivity of the process on the type of educt is studied and a number of examples of regiospecific conduct are cited. It is shown that aminomercuration offers easy access to a number of hetero ring systems like imidazoimidazoles, imidazopyrimidines, imidazo- and pyrimidoquinazolines,imidazo- and pyrimidodiazepines as well as benzoxazepines. The method promises utility in the synthesis of a variety of other heterocycles.