Format

Send to

Choose Destination
See comment in PubMed Commons below
Org Lett. 2013 May 3;15(9):2156-9. doi: 10.1021/ol4006695. Epub 2013 Apr 19.

Studies on the regioselective nucleophilic aromatic substitution (S(N)Ar) reaction of 2-substituted 3,5-dichloropyrazines.

Author information

1
La Jolla Laboratories, Pfizer, Inc., 10770 Science Center Drive, San Diego, California 92121, United States. stephanie.scales@pfizer.com

Abstract

Differences in regioselectivity were observed during the S(N)Ar reaction of amines with unsymmetrical 3,5-dichloropyrazines. This study revealed that when the 2-position of the pyrazine was occupied with an electron-withdrawing group (EWG), nucleophilic attack occurred preferentially at the 5-position. When the 2-position was substituted with an electron-donating group (EDG), nucleophilic attack occurred preferentially at the 3-position. These results are reported along with a computational rationale for the experimental observations based on the Fukui index at the reacting centers.

PMID:
23600718
DOI:
10.1021/ol4006695
[Indexed for MEDLINE]
PubMed Commons home

PubMed Commons

0 comments
How to join PubMed Commons

    Supplemental Content

    Full text links

    Icon for American Chemical Society
    Loading ...
    Support Center