Enantioselective synthesis of benzimidazolyl quinoxalinones on soluble polymer support using focused microwave irradiation.
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.
Chanda
Kaushik
K
Department of Applied Chemistry, National Chiao Tung University, Hsinchu, Taiwan 300-10, ROC.
Kuo
Jaren
J
Chen
Chih-Hau
CH
Sun
Chung-Ming
CM
D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry*; D020650:Combinatorial Chemistry Techniques / Q000379:methods*; D008872:Microwaves; D015394:Molecular Structure; D011108:Polymers / Q000737:chemistry; D011810:Quinoxalines / Q000138:chemical synthesis / Q000737:chemistry*; D012995:Solubility; D013237:Stereoisomerism
D001562:Benzimidazoles; D011108:Polymers; D011810:Quinoxalines