TY  - JOUR
N1  - This publication is Open Access under the license indicated.This publication is licensed under

CC-BY 4.0 .
cc licence
by licence
Copyright © 2020 American Chemical Society
SP  - 13438
Y1  - 2020/11/06/
TI  - tele-Substitution Reactions in the Synthesis of a Promising Class of 1,2,4-Triazolo[4,3-a]pyrazine-Based Antimalarials
EP  - 13452
AV  - public
JF  - The Journal of Organic Chemistry
N2  - We have discovered and studied a tele-substitution reaction in a biologically important heterocyclic ring system. Conditions that favor the tele-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 crystallographic and isotope labeling experiments, a mechanism for this unusual transformation is proposed. We focused on this triazolopyrazine as it is the core structure of the in vivo active antiplasmodium compounds of Series 4 of the Open Source Malaria consortium.
VL  - 85
UR  - https://doi.org/10.1021/acs.joc.0c01045
A1  - Korsik, M
A1  - Tse, EG
A1  - Smith, DG
A1  - Lewis, W
A1  - Rutledge, PJ
A1  - Todd, MH
IS  - 21
ID  - discovery10114909
KW  - Hydrocarbons
KW  -  Substitution reactions
KW  -  Chemical reactions
KW  -  Aromatic compounds
KW  -  Solvents
ER  -