Internal oxidation‐reduction of quinoxaline‐2‐ carboxaldehyde 1,4‐dioxide | Zendy

Kluge Arthur F. | Zendy; Maddox Michael L. | Zendy

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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.

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