<p></p><p>We
have discovered and studied a <i>tele</i>substitution reaction in a
biologically important heterocyclic ring system. Conditions that favour
the <i>tele</i>-substitution pathway were identified: the use of increased
equivalents of the nucleophile or decreased equivalents of base, or the use of
softer nucleophiles, less polar solvents and larger halogens on the
electrophile. Using results from X-ray crystallography and isotope labelling
experiments a mechanism for this unusual transformation is proposed. We focused
on this triazolopyrazine as it is the core structure of the <i>in
vivo </i>active anti-plasmodium compounds of Series 4 of the Open Source
Malaria consortium.</p>
<p> </p>
<p>Archive
of the electronic laboratory notebook with the description of all conducted
experiments and raw NMR data could be accessed via following link <a href="https://ses.library.usyd.edu.au/handle/2123/21890">https://ses.library.usyd.edu.au/handle/2123/21890</a> .
For navigation between entries of laboratory notebook please use file
"Strings for compounds in the article.pdf" that works as a reference
between article codes and notebook codes, also this file contain SMILES for
these compounds. </p><br><p></p>
