Synthesis of functionalized 2,4-imidazolidinone and 2-thioxoimidazolidin-4-one from an enantiomerically pure aziridine-2-carbaldehyde

ORGN 792

Baeck Kyoung Lee, baggaeng@hotmail.com1, Sae Young Yun1, Dong Sub Kim1, Won Koo Lee1, and Hyun-Joon Ha2. (1) Department of Chemistry and Interdisciplinary Program of Integrated Biotechnology, Sogang University in South Korea, Ricci Building unit1318 Sogang University Sin Su Dong #1 Mapo Gu, Seoul, South Korea, (2) Department of Chemistry, Hankuk University of Foreign Studies, Yongin 449-791, Kyung Gi Do, South Korea
Enantiomerically pure 1,3,5-functionalized 2,4-imidazolidinone and 2-thioxoimidazolidin-4-one were synthesized efficiently from the commercially available chiral aziridine carbaldehyde. The reaction includes the reductive coupling of the chiral aziridine-2-carboxaldehyde with a-amino ester, the addition of isocyanates or thioisocyanates and the subsequent intramolecular cyclization to provide the target compounds in high yields.

 

Combinatorial, Parallel and Process Chemistry, Heterocycles, Aromatics, New Reactions and Methodology
8:00 PM-10:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007