Tautomerism of guanidines studied by 15N NMR: 2-hydrazono-3-phenylquinazolin-4(3H)-ones and related compounds

Ion Ghiviriga; Bahaa El-Dien M. El-Gendy; Peter J. Steel; Alan R. Katritzky

doi:10.1039/B907577A

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Tautomerism of guanidines studied by ¹⁵N NMR: 2-hydrazono-3-phenylquinazolin-4(3H)-ones and related compounds†

Ion Ghiviriga,*^a Bahaa El-Dien M. El-Gendy,^bc Peter J. Steel^d and Alan R. Katritzky*^b

Author affiliations

* Corresponding authors

^a Chemistry Department, University of Florida, Gainesville, USA
E-mail: ion@chem.ufl.edu
Fax: +1 3528463001
Tel: +1 3528463001

^b Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, USA
E-mail: katritzky@chem.ufl.edu
Fax: +1 3523929199
Tel: +1 3523920554

^c Department of Chemistry, Faculty of Science, Benha University, Benha, Egypt

^d Chemistry Department, University of Canterbury, New Zealand
E-mail: peter.steel@canterbury.ac.nz
Fax: +64 3 364 2110
Tel: +64 3 364 2432

Abstract

2-Hydrazono-3-phenylquinazolin-4(3H)-ones 11a–i are shown by ¹⁵N NMR to exist in DMSO solution predominantly as the imino tautomers B and not the amino tautomers A. 2-Hydrazino-benzimidazole derivative 12 and 2-hydrazino-4,6-dimethylpyrimidine derivative 13 were found to exist predominantly as the amino tautomers.

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Supplementary files

Crystal structure data TXT (18K)

Article information

DOI: https://doi.org/10.1039/B907577A
Article type: Paper
Submitted: 16 Apr 2009
Accepted: 30 Jun 2009
First published: 11 Aug 2009

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Org. Biomol. Chem., 2009,7, 4110-4119

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Tautomerism of guanidines studied by ¹⁵N NMR: 2-hydrazono-3-phenylquinazolin-4(3H)-ones and related compounds

I. Ghiviriga, B. E. M. El-Gendy, P. J. Steel and A. R. Katritzky, Org. Biomol. Chem., 2009, 7, 4110 DOI: 10.1039/B907577A

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Organic & Biomolecular Chemistry