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Zeitschrift für Naturforschung B

A Journal of Chemical Sciences

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IMPACT FACTOR 2017: 0.757

CiteScore 2017: 0.68

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1865-7117
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Volume 73, Issue 5

Issues

2-Naphthol-pyrazole conjugates as substrates in the Mannich reaction

Gheorghe Roman
  • Corresponding author
  • Department of Inorganic Polymers, Petru Poni Institute of Macromolecular Chemistry, 700487 Iaşi, Romania
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Published Online: 2018-03-20 | DOI: https://doi.org/10.1515/znb-2017-0209

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.

This article offers supplementary material which is provided at the end of the article.

Keywords: 2-naphthols; aminomethylation; Mannich reaction; pyrazoles

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About the article

Received: 2017-12-12

Accepted: 2018-02-25

Published Online: 2018-03-20

Published in Print: 2018-05-24


Citation Information: Zeitschrift für Naturforschung B, Volume 73, Issue 5, Pages 275–280, ISSN (Online) 1865-7117, ISSN (Print) 0932-0776, DOI: https://doi.org/10.1515/znb-2017-0209.

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