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Scientia Pharmaceutica is published by MDPI from Volume 84 Issue 3 (2016). Articles in this Issue were published by another publisher in Open Access under a CC-BY (or CC-BY-NC-ND) licence. Articles are hosted by MDPI on mdpi.com as a courtesy and upon agreement with Austrian Pharmaceutical Society (Österreichische Pharmazeutische Gesellschaft, ÖPhG).
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Sci. Pharm. 2008, 76(1), 19-32; https://doi.org/10.3797/scipharm.0802-06 (registering DOI)

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

Department of Drug and Natural Product Synthesis, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria
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Received: 29 February 2008 / Accepted: 12 March 2008 / Published: 30 March 2008
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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
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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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.

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