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Synthesis 1992; 1992(6): 596-601
DOI: 10.1055/s-1992-26172
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Cyclic Guanidines; IV.1 Intramolecular Nucleophilic Aromatic Substitution of Hydrogen in (3-Nitrophenyl)guanidines

Franz Esser* , Karl-Heinz Pook
  • *Departments of Medicinal and Analytical Chemistry, Boehringer Ingelheim KG, D-6507 Ingelheim, Germany
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Publication Date:
17 September 2002 (online)

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Cyclization of substituted (3-nitrophenyl)guanidines is achieved in basic medium by nucleophilic displacement of hydrogen. The reaction offers a new route to benzimidazoles as well as to tricyclic imidazo-, pyrimido- and diazepino-benzimidazoles with uncommon substitution patterns. The mechanism of the redox process is investigated and the regioselectivity is discussed in terms of substrate structure and reaction conditions. An outline is given on the scope of the ring closure.