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  1. 1 Open Chemistry

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  1. 1 2005

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  1. 1 Chang L.-J.

  2. 1 Kulkarni M.

  3. 1 Sun C.-M.

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Parallel synthesis of novel benzimidazoles on a soluble polymer support

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Chang L.-J., Kulkarni M., Sun C.-M.
Open Chemistry
|
2005
|
vol. 3
|
issue 2
288-294
EN
Liquid phase combinatorial synthesis using a soluble polyethylene glycol (PEG) polymer support and commercially available 3-nitro-4-fluoro benzoic acid is carried out in order to create a molecular library of trisubstituted benzimidazoles. The PEG-ester conjugate of 3-nitro-4-fluoro benzoic acid is subjected to ipso-fluoro displacement by various primary amines. The nitro group is reduced under neutral conditions using excess zinc and ammonium chloride, producing the polymer-boundo-phenylene diamines. Reaction of the diamines with different aldehydes results in cyclisation to benzimidazoles. The polymer support is cleaved releasing the desired products in high yields and purity. All reactions are performed at room temperature. [...]
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