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- Title
Application of resin-bound reagents for the synthesis of benzimidazole derivatives.
- Authors
Ismail, M. Mohsen; Refaat, Hanan M.; Kamel, Mona M.; Nemr, M. Tawfik Mohamed
- Abstract
In an efficient exploitation of solid-phase chemistry, this work describes the preparation of the new resin-bound 4-(N-arylamino)-3-aminobenzoates and their successful cyclocondensations with the sodium bisulfite adducts of different aldehydes and triethyl orthoformate or triethyl orthoacetate, followed by resin cleavage to produce the target 1,2-diaryl- and 1-aryl-2-(un)substituted benzimidazole-5-carboxylic acid derivatives, respectively. In another variation, the cyclocondensation of the resin-bound 4-(N-arylamino)-3-aminobenzoates with carbon disulfide afforded the corresponding resin-bound thioxobenzimidazoles, which upon cleavage gave the corresponding 2-thioxobenzimidazoles. S-Alkylation of the resin-bound thioxobenzimidazoles with benzyl chloride and 4-bromophenacyl bromide furnished 2-benzylsulfanyl benzimidazoles and 4-bromophenyl-2-oxoethylsulfanyl-benzimidazoles, respectively. Reacting the resin-bound 4-(N-arylamino)-3-aminobenzoates with phenyl isothiocyanate gave the open-form 4-(arylamino)-3-(3-phenylthioureido) benzoic acids. Moreover, the reaction of the resin-bound 4-(N-arylamino)-3-aminobenzoates with N,N-carbonyldiimidazole yielded the corresponding 2-bezimidazolones.
- Subjects
SOLID-phase synthesis; SOLID-phase biochemistry; CARBOXYLIC acid derivatives; BENZIMIDAZOLE derivatives; PHARMACEUTICAL chemistry
- Publication
Journal of Chemical Research, 2016, Vol 40, Issue 8, p478
- ISSN
1747-5198
- Publication type
Article
- DOI
10.3184/174751916X14665014807629