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Sci. Pharm.
Volume 76
Issue 1
10.3797/scipharm.0802-06
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Article

On the Synthesis and Reactivity of 4-(Oxiran-2-ylmethoxy)cinnoline: Targeting a Cinnoline Analogue of Propranolol

by
Wolfgang HOLZER
*,
Gernot A. ELLER
and
Simeon SCHÖNBERGER
Department of Drug and Natural Product Synthesis, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria
*
Author to whom correspondence should be addressed.
Sci. Pharm. 2008, 76(1), 19-32; https://doi.org/10.3797/scipharm.0802-06
Submission received: 29 February 2008 / Accepted: 12 March 2008 / Published: 30 March 2008
Versions Notes

Abstract

The title compound (2) was prepared by reaction of 4-chlorocinnoline with glycidol/sodium hydride in dry DMF, since treatment of cinnolin-4-ol with epichlorohydrin as well as oxidation of 4-allyloxycinnoline did not succeed. Reaction of 2 with primary and secondary amines leads to aminoalcohols characterized by a high tendency to rearrangement and/or elimination. The obtained products were subjected to detailed multinuclear (1H, 13C, 15N) NMR studies.
Keywords: Cinnolines; Cinnolin-4(1H)-one; Epoxides; Nucleophilic Substitution; NMR Spectroscopy Cinnolines; Cinnolin-4(1H)-one; Epoxides; Nucleophilic Substitution; NMR Spectroscopy

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MDPI and ACS Style

HOLZER, W.; ELLER, G.A.; SCHÖNBERGER, S. On the Synthesis and Reactivity of 4-(Oxiran-2-ylmethoxy)cinnoline: Targeting a Cinnoline Analogue of Propranolol. Sci. Pharm. 2008, 76, 19-32. https://doi.org/10.3797/scipharm.0802-06

AMA Style

HOLZER W, ELLER GA, SCHÖNBERGER S. On the Synthesis and Reactivity of 4-(Oxiran-2-ylmethoxy)cinnoline: Targeting a Cinnoline Analogue of Propranolol. Scientia Pharmaceutica. 2008; 76(1):19-32. https://doi.org/10.3797/scipharm.0802-06

Chicago/Turabian Style

HOLZER, Wolfgang, Gernot A. ELLER, and Simeon SCHÖNBERGER. 2008. "On the Synthesis and Reactivity of 4-(Oxiran-2-ylmethoxy)cinnoline: Targeting a Cinnoline Analogue of Propranolol" Scientia Pharmaceutica 76, no. 1: 19-32. https://doi.org/10.3797/scipharm.0802-06

APA Style

HOLZER, W., ELLER, G. A., & SCHÖNBERGER, S. (2008). On the Synthesis and Reactivity of 4-(Oxiran-2-ylmethoxy)cinnoline: Targeting a Cinnoline Analogue of Propranolol. Scientia Pharmaceutica, 76(1), 19-32. https://doi.org/10.3797/scipharm.0802-06

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