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Efficient Synthesis of Quinoxaline Derivatives by Selective Modification of 3‐Chloro‐6‐fluoroquinoxalin‐2(1 H )‐one 4‐Oxide
Author(s) -
Maichrowski Jan,
Gjikaj Mimoza,
Hübner Eike G.,
Bergmann Bärbel,
Müller Ingrid B.,
Kaufmann Dieter E.
Publication year - 2013
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201201569
Subject(s) - quinoxaline , chemistry , annulation , amide , reactivity (psychology) , combinatorial chemistry , density functional theory , oxide , organic chemistry , stereochemistry , medicinal chemistry , computational chemistry , catalysis , medicine , alternative medicine , pathology
The readily available and polyfunctionalized 3‐chloro‐6‐fluoroquinoxalin‐2(1 H )‐one 4‐oxide, derived from the efficient one‐step annulation reaction of 1,1,2‐trichloro‐2‐nitroethene with 4‐fluoroaniline, was selectively modified at the chloronitrone and the amide units, leading to more than 30 new quinoxaline derivatives with a unique substitution pattern in good to excellent yields. In addition, the electronic properties of the versatile starting compound were computed by means of density functional theory, which gave a reasonable explanation for its unique reactivity. The antimalarial activity of all hitherto unknown compounds has been investigated.