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An Efficient Synthesis of New Azomethine Ylide: 1-(Diaminomethyl-eneammonio)(aryl) methyl-4,4-dimethyl-2,6-dioxocyclohexan-1-ide under Solvent-Free Conditions
Received date: 2016-06-13
Revised date: 2016-08-10
Online published: 2016-09-01
Supported by
Project supported by the Natural Science Foundation of Jiangsu Normal University(No. HXKY2015B001), the Priority Academic Program Development of Jiangsu Higher Education Institutions and the Brand Major of Universities in Jiangsu Province.
The zwitterionic compounds 1-(diaminomethyleneammonio)(aryl) methyl-4,4-dimethyl-2,6-dioxocyclohexan-1-ides were synthesized from the reaction of dimedone,aromatic aldehydes and guanidine carbonate catalyzed by NaOH under solvent-free conditions.This is the new type azomethine ylide compound that has not been reported previously.The other advantages of this reaction were simple operation,short reaction time,and environmental friendly.The products were identified by 1H NMR,13C NMR,IR and HRMS,and that of 4a was additionally confirmed by X-ray diffraction analysis.This reported approach is an effective way for the synthesis of azomethine ylide.
Key words： dimedone; guanidine carbonate; azomethine ylide; green synthesis
Meng Zhiying , Gu Mengmeng , Wang Mengyao , Xu Jing , Gao Xu , Hao Ganlu , Rong Liangce . An Efficient Synthesis of New Azomethine Ylide: 1-(Diaminomethyl-eneammonio)(aryl) methyl-4,4-dimethyl-2,6-dioxocyclohexan-1-ide under Solvent-Free Conditions[J]. Chinese Journal of Organic Chemistry, 2017 , 37(1) : 213 -217 . DOI: 10.6023/cjoc201606021
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