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Paper | Special issue | Vol 99, No. 1, 2019, pp.267-278
Published online, 13th August, 2018
DOI: 10.3987/COM-18-S(F)20
Diastereoselective Synthesis of Poly-Substituted syn-Imidazolidine-2-thiones via Microwave-Assisted Three-Component [2+2+1] Heterocyclizations

Jie-Yu Hu, Yi-Yun Gao, Wen-Wen Zhang, Ke-Ying Zhang, Wen-Lian Li, Wen-Juan Hao,* Bo Jiang, and Guigen Li*

*Department of Chemistry and Biochemistry, Texas Tech University, Lubbock, TX 79409-1061, U.S.A.

Abstract

An efficient and simple three-component reaction of arylglyoxals, isothiocyanates and arylamines has been developed, delivering poly-substituted syn-imidazolidine-2-thione derivatives with high diastereo- and regioselectivity (up to > 99:1). The microwave-assisted transformation is easy to perform simply by mixing readily available starting materials, thereby featuring mild reaction conditions, bond-forming efficiency and atom-economy.