Next Article in Journal
Derivatization with 4-Chloro-7-nitro-2,1,3-benzoxadiazole for the Spectrophotometric and Differential Pulse Polarographic Determination of Acetylcysteine and Captopril
Previous Article in Journal
The Similarity Principle – New Trends and Applications in Ligand-Based Drug Discovery and ADMET Profiling
Article Menu

Article Versions

Export Article

Open AccessArticle
Sci. Pharm. 2008, 76(1), 19-32; doi: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
*
Author to whom correspondence should be addressed.
Received: 29 February 2008 / Accepted: 12 March 2008 / Published: 30 March 2008
Download PDF [222 KB, uploaded 27 December 2016]

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).

Scifeed alert for new publications

Never miss any articles matching your research from any publisher
  • Get alerts for new papers matching your research
  • Find out the new papers from selected authors
  • Updated daily for 49'000+ journals and 6000+ publishers
  • Define your Scifeed now

SciFeed Share & Cite This Article

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.

Show more citation formats Show less citations formats

Article Metrics

Article Access Statistics

1

Comments

[Return to top]
Sci. Pharm. EISSN 2218-0532 Published by MDPI AG, Basel, Switzerland RSS E-Mail Table of Contents Alert
Back to Top