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Permanganate Oxidation of Quinoxaline and Its Derivatives
Author(s) -
Obafemi Craig A.,
Pfleiderer Wolfgang
Publication year - 1994
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19940770610
Subject(s) - chemistry , quinoxaline , permanganate , yield (engineering) , potassium permanganate , medicinal chemistry , organic chemistry , stereochemistry , metallurgy , materials science
The oxidation reactions of a series of quinoxaline derivatives, using KMnO 4 in the presence or absence of NaOH, are described. Neutral oxidation of 2‐chloro‐ and 2, 3‐dichloroquinoxalines 2 – 4 afforded the corresponding chloro‐ and dichloropyrazinedicarboxylic acids 13 and 14 in good yield. On the other hand, oxidation of quinoxalin‐2(1 H )‐one and 1, 4‐dihydroquinoxaline‐2, 3‐dione derivatives in alkaline medium gave different products, with the quinoxalin‐2(1 H )‐one ( 5 ) forming 1, 4‐dihydroquinoxaline‐2, 3‐dione ( 9 ), while various substituted quinoxalin‐2, 3‐dione derivatives (see 9 – 11 ) gave a new type of dimeric products. The structural assignments for the new compounds were based on spectroscopic data.