Ring-enlargement of dimethylaminopropenoyl cyclopropanes: an efficient route to substituted 2,3-dihydrofurans.
A convenient and efficient synthesis of substituted dihydrofurans is developed via ring-enlargement of 1-dimethylaminopropenoyl-1-carbamoyl/benzoyl cyclopropanes 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]pyridin-4(5H)-ones in high yields.
Zhang
Rui
R
Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China.
Liang
Yongjiu
Y
Zhou
Guangyuan
G
Wang
Kewei
K
Dong
Dewen
D
D000085:Acetates / Q000737:chemistry; D019342:Acetic Acid / Q000737:chemistry; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000085:Acetates; D003521:Cyclopropanes; D005663:Furans; C073812:2,3-dihydrofuran; D019342:Acetic Acid; C018824:ammonium acetate