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Sci Pharm. 2008; 76: 19–32

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

Wolfgang HOLZER *, Gernot A. ELLER, Simeon SCHÖNBERGER

Department of Drug and Natural Product Synthesis, University of Vienna, Althanstrasse 14, A-1090 Vienna, Austria

* Corresponding author: Tel.: +43-1-4277-55623; Fax: +43-1-4277-9556.
E-mail: (W. Holzer).


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.


Cinnolines • Cinnolin-4(1H)-one • Epoxides • Nucleophilic Substitution • NMR Spectroscopy

Received February 29th, 2008 | Accepted March 12th, 2008 | Published Online March 30th, 2008