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Internal oxidation‐reduction of quinoxaline‐2‐ carboxaldehyde 1,4‐dioxide
Author(s) -
Kluge Arthur F.,
Maddox Michael L.
Publication year - 1980
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570170552
Subject(s) - chemistry , cyanohydrin , methanol , acetone , decarboxylation , cyanide , quinoxaline , organic chemistry , medicinal chemistry , catalysis
Reaction of carboxaldehyde 1 with acetone cyanohydrin gives carboxylic acid 2. Reaction of 1 with acetone cyanohydrin in methanol affords the methyl ester 3. The structural assignment for 2 is supported by 13 C nmr data and by the decarboxylation of deuterated 2 to give 4b. The internal oxidation‐reduction upon going from 1 to 2 is explained in terms of a mechanism whereby 1 is converted into its cyanohydrin 5 and then to acyl cyanide 6. Acyl cyanide 6 then reacts with either water or methanol to give 2 or 3.