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- Title
2-Naphthol-pyrazole conjugates as substrates in the Mannich reaction.
- Authors
Roman, Gheorghe
- Abstract
Several novel 2-naphthol-pyrazole conjugates have been synthesized through the O-alkylation of 1-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]naphthalen-2-ol with methyl iodide, benzyl chloride, methyl bromoacetate and N-benzyl-2-bromoacetamide. The aminomethylation of these 2-naphthol-pyrazole conjugates has been examined employing the classical conditions for the Mannich reaction, and also by using N,N-dimethylmethyleneiminium chloride as preformed aminomethylating reagent. In both situations, aminomethylation of these substrates occurred at C-4 of the pyrazole ring. The bifunctional substrate 1-[(3,5-dimethyl-1H-pyrazol-1-yl)methyl]naphthalen-2-ol has been chemoselectively aminomethylated in the pyrazole ring using the same preformed aminomethylating reagent.
- Subjects
NAPHTHOL; PYRAZOLES; METHYL iodide; BENZYL chloride; CHEMOSELECTIVITY; MANNICH reaction
- Publication
Zeitschrift für Naturforschung B: A Journal of Chemical Sciences, 2018, Vol 73, Issue 5, p275
- ISSN
0932-0776
- Publication type
Academic Journal
- DOI
10.1515/znb-2017-0209