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I2-promoted tandem cyclization to synthesize polysubstituted pyrano[3,2-c]chromene-2,5-diones
Authors:Qun Cai  Shiyi Zhuang  Mian Yang  Na Peng  Yi Liu  Anxin Wu
Affiliation:1. Coal Conversion and New Carbon Materials Key Laboratory of Hubei Province, School of Chemistry and Chemical Engineering, Wuhan University of Science and Technology, Wuhan, 430081, PR China;2. Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan, 430079, PR China;3. State Key Laboratory of Virology & Key Laboratory of Analytical Chemistry for Biology and Medicine(MOE), College of Chemistry and Molecular Sciences, Wuhan University, Wuhan, 430072, PR China
Abstract:
An efficient and convenient method for the synthesis of various substituted pyrano[3,2-c]chromene-2,5-diones was developed via the I2-promoted tandem cyclization of commercially available aryl methyl ketones and 4-hydroxycoumarins. Preliminary mechanism studies indicated that the reaction involved a consecutive iodination/Kornblum oxidation/annulation process. HI produced in the I2-DMSO system acted as an important promoter, accelerating the annulation protocol.
Keywords:Corresponding author.  Tandem cyclization  Aryl methyl ketones  4-Hydroxycoumarins
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