Synthesis of 2, 3-dihydroimidazo [1, 2-a] pyrimidin-5 (1H)-ones by the domino Michael addition retro-ene reaction of 2-alkoxyiminoimidazolidines and acetylene …

J Sączewski, Z Brzozowski, M Gdaniec

Index: Saczewski, Jaroslaw; Brzozowski, Zdzislaw; Gdaniec, Maria Tetrahedron, 2005 , vol. 61, # 22 p. 5303 - 5309

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Citation Number: 17

Abstract

2-Alkoxyiminoimidazolidines react with acetylene dicarboxylates and ethyl phenylpropiolate to give 8-alkoxy-imidazo [1, 2-a] pyrimidin-5 (3H)-ones, which subsequently undergo a sterically induced multihetero-retro-ene fragmentation to give imidazo [1, 2-a] pyrimidin-5 (1H)-ones together with formaldehyde or benzaldehyde. On the other hand, a similar reaction of with ethyl propiolate gives corresponding 8-alkoxy-imidazo [1, 2-a] pyrimidin-5 ...