Halonium-initiated double oxa-cyclization cascade as a synthetic strategy for halogenated furo[3,2-c]pyran-4-ones.
The reaction of 1-alkenoylcyclopropane carboxylic acids with NBS or NIS was investigated, which provides an efficient route to biologically important 7-halogenated furo[3,2-c]pyran-4-ones in a one-pot transformation. The major pathway for the formation of the O-O heterocycles was proposed as a halo-oxa-cyclization, HBr elimination, cyclopropane ring-opening and recyclization (intramolecular oxa-cyclization), and bromination cascade. The double-oxa-cyclization represents a novel synthetic strategy towards functionalized furo[3,2-c]pyranones.
Department of Chemistry, Northeast Normal University, Changchun 130024, China. liangfs112@nenu.edu.cn.
Enxiang
E
Wei
Bing
B
Liu
Shaoxia
S
Lin
Baozhong
B
Zhao
Fushun
F
Liang
D018360:Crystallography, X-Ray; D003500:Cyclization; D006846:Hydrocarbons, Halogenated / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D011753:Pyrones / Q000737:chemistry*
D006846:Hydrocarbons, Halogenated; D011753:Pyrones; C581776:furo(3,2-c)pyran-4-one; D010100:Oxygen