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Communication | Regular issue | Vol 83, No. 1, 2011, pp.47-55
Published online, 12th November, 2010
DOI: 10.3987/COM-10-12072
Facile Synthesis of 3-(Succinimid-3-yl)-2-oxo-2,3-dihydroimidazo[1,2-a]pyridine Derivatives by Sequential Intra- and Intermolecular Michael Reactions between 2-Aminopyridines and Maleimides

Tetsuro Shimo,* Tomoko Itoh, Yasutaka Araki, Tetsuo Iwanaga, Teruo Shinmyozu, and Kenichi Somekawa

*Department of Applied Chemistry and Chemical Engineering, Faculty of Engineering, Kagoshima University, Korimoto, Kagoshima 890, Japan

Abstract

3-(Succinimid-3-yl)-2-oxo-2,3-dihydroimidazo[1,2-a]pyridine derivatives (3 and 4) were prepared through a one-pot reaction from 2-aminopyridines (1) by acylation with maleimides (2) and followed by an intramolecular Michael addition, and a subsequent second Michael addition with another molecule of 2. The diastereomeric configurations of the products were confirmed by X-ray crystal analyses. The reaction mechanism of the accumulated three types of additions between 1 and two equimolar amounts of 2 was calculated using MOPAC-PM6 molecular simulations and the competing addition reactions as hard and soft reactions were explained by HSAB theory.