Glyoxylic acid and MP-glyoxylate: efficient formaldehyde equivalents in the 3-CC of 2-aminoazines, aldehydes, and isonitriles.
[reaction: see text] Glyoxylic acid, either in solution or immobilized on MP-carbonate (MP-glyoxylate), participates in an uncatalyzed 3-CC with 2-aminoazines and isonitriles to afford novel 2-unsubstituted-3-amino-imidazoheterocycles. MP-glyoxylate serves as a particularly efficient and experimentally convenient formaldehyde equivalent and readily liberates products through decarboxylation/self-release from the resin. These examples furthermore constitute the first application in which MP-CO3 serves as a solid support for transformations involving carboxylic acids.
Lyon
Michael A
MA
Array BioPharma Inc., 3200 Walnut Street, Boulder, Colorado 80301, USA.
Kercher
Timothy S
TS
D000447:Aldehydes / Q000737:chemistry*; D001393:Azoles / Q000737:chemistry*; D003500:Cyclization; D006038:Glyoxylates / Q000737:chemistry*; D007093:Imidazoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry*
D000447:Aldehydes; D001393:Azoles; D006038:Glyoxylates; D007093:Imidazoles; D009570:Nitriles; C031150:glyoxylic acid