Glyoxylic acid and MP-glyoxylate: Efficient formaldehyde equivalents in the 3-CC of 2-aminoazines, aldehydes, and isonitriles

Organic Letters

Volumn 6, Issue 26, 2004, Pages 4989-4992

  Lyon, Michael A ^a   Kercher, Timothy S ^a  

^a ARRAY BIOPHARMA INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINOPYRIDINE; ALDEHYDE; CARBONIC ACID DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; FORMALDEHYDE; GLYOXYLIC ACID; HETEROCYCLIC COMPOUND; ISONITRILE DERIVATIVE; RESIN;

ARTICLE; CATALYSIS; DECARBOXYLATION; SOLID;

ALDEHYDES; AZOLES; CYCLIZATION; GLYOXYLATES; IMIDAZOLES; MOLECULAR STRUCTURE; NITRILES;

EID: 12344257726     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0478234     Document Type: Article

References (29)

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25. ArgoPore is a registered trademark of Argonaut Technologies.
26. 3 was purchased from Argonaut Technologies at a claimed loading of 2.62 mmol/g.
27. Freshly prepared MP-glyoxylate was employed for all reactions. See Supporting Information for experimental procedures.
28. 13C NMR, and MS analysis.
29. During the attempted purification of products 2f-h, significant amounts of unreacted aminoazine substrate were detected. When method A was used with prolonged reaction times, the imine derived from methyl glyoxylate and the aminoazine was also isolated, thus suggesting esterification as a competitive reaction in the absence of 3-CC/decarboxylation activity.