American Chemical Society
ao0c01930_si_002.pdf (3.19 MB)

NaH Promoted One-Pot Tandem Reactions of 3‑(1-Alkynyl) Chromones to Form 2‑Nitrogen-Substituted Xanthones

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journal contribution
posted on 2020-05-28, 12:07 authored by Wen-Di Duan, Yu-Fang Zhang, Youhong Hu
A silver-catalyzed dimerization of ethyl isocyanoacetates could trigger the tandem reaction of 3-(1-alkynyl) chromones under the basic condition in a one-pot reaction to afford xanthone skeletons with 2-imidazolyl substitution in an efficient manner. With the control experiment in hand, a mechanism including dimerization of isocyanoacetate/deprotonation/Michael addition/ring-opening/cyclization 1,2-elimination was deduced. Further investigation for the base was carried out, resulting in NaH as an optimal base to avoid the dimerization of 3-(1-alkynyl) chromones. The scope of this methodology was extended on the different substituents of 3-(1-alkynyl)-chromones and the potential of other N-heterocycle glycine ester anions to give the novel functional 2-nitrogen-derived xanthones.