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1H, 13C and 15N NMR assignments of phenazopyridine derivatives

✍ Scribed by Eleuterio Burgueño-Tapia; Yolanda Mora-Pérez; Martha S. Morales-Ríos; Pedro Joseph-Nathan

Publisher
John Wiley and Sons
Year
2004
Tongue
English
Weight
120 KB
Volume
43
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

Phenazopyridine hydrochloride (1), a drug in clinical use for many decades, and some derivatives were studied by one‐ and two‐dimensional ^1^H, ^13^C and ^15^N NMR methodology. The assignments, combined with DFT calculations, reveal that the preferred protonation site of the drug is the pyridine ring nitrogen atom. The chemoselective acetylation of phenazopyridine (2) and its influence on the polarization of the azo nitrogen atoms were evidenced by the ^15^N NMR spectra. Molecular calculations of the phenazopyridines 2–4 show that the pyridine and phenyl groups are oriented in an antiperiplanar conformation with intramolecular hydrogen bonding between the N‐b atom and the C‐2 amino group preserving the E‐azo stereochemistry. Copyright © 2004 John Wiley & Sons, Ltd.

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