Synthesis of Dibenzocyclohepten-5-ones by Electrophilic Iodocyclization of 1-([1,1鈥?Biphenyl]-2-yl)alkynones

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• 作者：Yu Chen ; Chenlong Huang ; Xiaochen Liu ; Eliyahu Perl ; Zhiwei Chen ; Jieun Namgung ; Gopal Subramaniam ; Gan Zhang ; William H. Hersh
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：April 18, 2014
• 年：2014
• 卷：79
• 期：8
• 页码：3452-3464
• 全文大小：587K
• 年卷期：v.79,no.8(April 18, 2014)
• ISSN：1520-6904

文摘

A synthesis of iodo-substituted dibenzocyclohepten-5-ones by the iodine monochloride (or iodine)-induced intramolecular 7-endo-dig cyclization of 1-([1,1鈥?biphenyl]-2-yl)alkynones is reported. Detailed investigations on the substituent effects during the electrophilic iodocyclization of the alkynones show that they play a crucial role in determining the reaction pathways of the cyclization. By modifying the substitution pattern on the alkynone substrates, the cyclization takes place regioselectively, leading to either dibenzocyclohepten-5-ones, via a 7-endo-dig cyclization, or spiroconjugated compounds, via a 6-endo-dig cyclization.