Journal
TETRAHEDRON
Volume 61, Issue 22, Pages 5303-5309Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2005.03.063
Keywords
2,3-dihydroimidazo[1,2-alpha]pyrimidin-5(1H)-ones; 8-alkoxyimidazo[1,2-alpha]pyrimidin-5(3H)-ones; domono Michael addition retro-ene reacion; N-alkylation; N-acylation; N-formylation; X-ray crystal structure analysis
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2-Alkoxyiminoimidazolidines 2-3 react with acetylene dicarboxylates and ethyl phenylpropiolate to give 8-alkoxy-imidazo[1,2a]pyrimidin-5(3H)-ones C, which subsequently undergo a sterically induced multihetero-retro-ene fragmentation to give imidazo[1,2a]pyrimidin-5(1H)-ones 4-7 together with formaldehyde or benzaldehyde. On the other hand, a similar reaction of 2-3 with ethyl propiolate gives corresponding 8-alkoxy-imidazo[1,2-a]pyrimidin-5(3H)-ones 8-10. The unsubstituted imidazo[1,2-a]pyrimidin-5(1H)-one 11 can be prepared by retro-ene reaction of 9 upon prolonged heating in refluxing ethanol. A direct synthetic approach to 1-formyl-7-phenyl-imidazo[1,2-a]pyrimidine-5(1H)-one 14 is reported using DMF/sulfonyl chloride as a new Vilsmeier-type N-formylating reagent. (c) 2005 Elsevier Ltd. All rights reserved.
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