4.7 Article

Ring-enlargement of dimethylaminopropenoyl cyclopropanes: An efficient route to substituted 2,3-dihydrofurans

期刊

JOURNAL OF ORGANIC CHEMISTRY
卷 73, 期 20, 页码 8089-8092

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AMER CHEMICAL SOC
DOI: 10.1021/jo801289p

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  1. National Natural Science Foundation of China [20572013, 20711130229]
  2. Ministry of Education of China [105061]
  3. Department of Science and Technology of Jilin Province [20050309]

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A convenient and efficient synthesis of substituted dihydrofurans is developed via ring-enlargement of 1-dimethylaminopropenoyl-1-carbamoyl/benzoyl cycloproparres catalyzed by ammonium acetate in acetic acid with high regio- and stereoselectivity. Some of the newly synthesized substituted dihydrofurans are subjected to further synthetic transformation in the presence of NaOH (aq) in ethanol to afford the corresponding 5-aryl-2,3-dihydrofuro[3,2-c]pyfidin-4(5H)-ones in high yields.

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