Molecular diversity of cycloaddition reactions of the functionalized pyridinium salts with 3-phenacylideneoxindoles

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• 作者：Qin Fu ; Chao-Guo Yan ; ^{cgyan@yzu.edu.cn}
• 关键词：Heterocycle ; Spiro compound ; Pyridinium N-ylide ; Oxindole ; Cyclopropane
• 刊名：Tetrahedron
• 出版年：2013
• 出版时间：22 July, 2013
• 年：2013
• 卷：69
• 期：29
• 页码：5841-5849
• 全文大小：678 K

文摘

The cycloaddition reactions of a series of functionalized pyridinium salts, which were generated from reaction of pyridine with active alkyl halides such as p-nitrobenzyl bromide, N,N-diethyl chloroacetamide and phenacyl bromides with 3-phenacylideneoxindoles in the presence of triethylamine showed very interesting molecular diversities. A series of the functionalized spiro[cyclopropane-1,3¡ä-indolines], and 3-furan-3(2H)-ylidene)indolin-2-ones were successfully prepared depending upon the structures of the pyridinium salts and reaction conditions. The regioselectivity and stereoselectivity of the reactions as well as reaction mechanisms were briefly discussed.