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Synthese und Umlagerungsreaktionen von 2‐(2‐Amino‐anilino)‐2‐imidazolin‐Derivaten
Author(s) -
Härter H. P.,
Stauss U.,
Schindler O.
Publication year - 1971
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19710540745
Subject(s) - chemistry , benzimidazole , derivative (finance) , ethylenediamine , ethylene diamine , medicinal chemistry , hydrolysis , benzoyl chloride , amidine , diamine , disproportionation , nitro , stereochemistry , polymer chemistry , organic chemistry , alkyl , catalysis , financial economics , economics , nuclear chemistry
The nitro‐imidazolines V and VI are formed by addition reaction of ethylenediamine to the isothiocyanates III and IV. The nitro group is then converted by hydrogenation to the amino group, giving XI and XII, which can be acylated selectively to IX and X. By rearrangement in boiling xylene, the compounds XI and XII give the corresponding 2‐(2‐aminoethylamino)‐benzimidazoles XIII and XIV. The benzoylated derivative IX gives the benzimidazole derivative XVIII by rearrangement and subsequent migration of the benzoyl group, while the benzylated derivative XVI gives the rearranged benzimidazole XXII. The benzimidazole structure of the rearranged products is proven by unambiguous synthesis of XIII, starting with 2‐chlorobenzimidazole (VII) and mono‐N‐acetyl‐ethylene‐diamine to give compound VIII, from which XIII is obtained by hydrolysis.