Enantioselective synthesis of benzimidazolyl quinoxalinones on soluble polymer support using focused microwave irradiation

Journal of Combinatorial Chemistry
Kaushik ChandaChung-Ming Sun

Abstract

Focused microwave irradiation has been applied to a multistep synthetic sequence of reactions designed to generate benzimidazolyl quinoxalinones using a soluble polymer support. They were obtained by the ipso-fluoro (S(N)Ar) displacement of the immobilized ortho-nitro fluoro benzimidazoles with chiral alpha amino esters under microwave irradiation. Intermediate chiral organic-polymer conjugates when subjected to neutral reduction underwent a spontaneous intramolecular ring closure. Cleavage of the polymer support, at room temperature, did not cause any significant racemization resulting in the generation of a chiral molecular library with two points of structural diversity.

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Citations

Oct 1, 2010·Chemical Communications : Chem Comm·Gegen TanaKazuhiro Chiba
May 29, 2012·Chemical Science·Shane L MangoldLaura L Kiessling
Sep 14, 2010·Journal of Combinatorial Chemistry·Ya-Shan HsiaoChung-Ming Sun

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