Acylierung von Heterocyclen mit Kohlensäurederivaten. II. Endo‐ und exo‐Carbamoylierung von 2‐Amino‐benzimidazol‐Derivaten mit Isocyanaten. Mechanismus der Acylgruppenwanderung

Acylation of Heterocycles with Carbonic Acid Derivatives. II. Endo and Exo Carbamoylation of 2‐Amino‐benzimidazole Derivatives with Isocyanates. Mechanism of the Acyl Group Migration 2‐Amino‐benzimidazoles react with isocyanates with good yields to give 2‐amino‐1‐carbamoyl‐aminobenzimidazoles 1 at −...

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Bibliographic Details
Published in:Journal für Praktische Chemie
Main Authors: Graubaum, Heinz, Martin, Dieter, Szeibert, Dagmar, Breckner, Michael, Glatt, Hans Horst, Bacaloglu, Radu, Czunderlick, Carol
Format: Article in Journal/Newspaper
Language:English
Published: Wiley 1982
Subjects:
Carbonic acid
Online Access:http://dx.doi.org/10.1002/prac.19823240515
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Summary:Acylation of Heterocycles with Carbonic Acid Derivatives. II. Endo and Exo Carbamoylation of 2‐Amino‐benzimidazole Derivatives with Isocyanates. Mechanism of the Acyl Group Migration 2‐Amino‐benzimidazoles react with isocyanates with good yields to give 2‐amino‐1‐carbamoyl‐aminobenzimidazoles 1 at −30°C and the corresponding 2‐carbamoyl isomeres 2 at room temperature, respectively. The isomerization mechanism was studied by crossover experiments and kinetic measurements and has been found to consist of inter‐ and monomolecular acyl transfer.

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