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

Autor:	Yu-Fang Zhang, Wen-Di Duan, Youhong Hu
Jazyk:	angličtina
Rok vydání:	2020
Předmět:	chemistry.chemical_compound Chemistry Tandem Cascade reaction General Chemical Engineering Xanthone chemistry.chemical_element Organic chemistry General Chemistry Nitrogen QD1-999 Article
Zdroj:	ACS Omega, Vol 5, Iss 22, Pp 13454-13461 (2020) ACS Omega
ISSN:	2470-1343
Popis:	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.
Databáze:	OpenAIRE
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