ArticleChemistry (Weinheim an der Bergstrasse, Germany)2026
Triggering and Preventing Cyclization of o-Amino-Guanidinobenzenes to 2-Amino-Benzimidazoles.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 1 paper.
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1 citing paper in PubMed.
- Triggering and Preventing Cyclization of o-Amino-Guanidinobenzenes to 2-Amino-Benzimidazoles.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
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6 authors.
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Abstract
Aromatic compounds in which a primary or secondary amino group is positioned next (in ortho position) to a guanidino group have been reported as intermediates in a variety of reactions, but are generally prone to cyclization to give 2-amino-imidazoles. Here, we present a comprehensive analysis, based on experiments and quantum-chemical calculations, of the stability and reactivity of these compounds. It is shown that cyclization reactions are triggered by Brønsted and Lewis acids. The analysis discloses strategies allowing to prevent cyclization by careful choice of the guanidino group and/or substituent at the amino group. The results of this analysis allowed the synthesis of first unsymmetrical diguanidinobenzene molecules and coordination compounds with o-amino-guanidinobenzene ligands, paving the way for the development of aromatic compounds with adjacent amino and guanidino groups as a versatile class of redox-active organic molecules.
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