Keywords
aminophenols
aromatic nucleophilic substitution
pyrimidine N-oxides
pyrimidines
Smiles rearrangement
tetrahydroquinazolines
Abstract
The SNAr reactions of 4-chloro- or 4-fluorotetrahydroquinazolines with 2-aminophenol as the O-nucleophile under basic conditions are accompanied by the Smiles rearrangement to afford the formal N-substitution 2-hydroxyphenylamino product. The similar reactions of N1-oxides disfavor the rearrangement allowing for the formation of O-substitution analog.
Funders
Ministry of Education and Science of the Russian Federation
121021000105-7
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