A direct
ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could
be stereospecifically synthesized in a tunable manner. This strategy
might not only enable a new ring-opening method of N1-H-1,2,3-triazoles under nonmetal catalysis and mild reaction conditions
but also offer a good opportunity to reliably access versatile (Z)-β-substituted enamides that could be used as synthetic
precursors for further synthetic transformations.
We here reported a direct ring-opening/semipinacol rearrangement reaction of 4-(1-hydroxycyclobutyl)-1,2,3-triazole, in which N-acyl substituted 1,2,3-triazole was generated in situ and would trigger thermodynamically controlled electrocyclization ring-opening to afford rearrangement precursor...
Nucleophilic
aromatic substitution (SNAr) reaction in
classic textbook is a stepwise mechanism, and few examples of concerted
reactions have been reported. Herein, we developed a concerted SNAr reaction of 5-bromo-1,2,3-triazines with phenols in which
the nonclassic mechanism of this reaction could be revealed by calculation.
Furthermore, the resulting 5-aryloxy-1,2,3-triazines could be used
as convenient precursors to access biologically important 3-aryloxy-pyridines
in one-pot manner.
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