Solid phase vs. solution phase differential behavior: formation of a salicylate structure from a malondialdehyde moiety.
Treatment of 2, solid supported synthetic equivalent of 3-formylchromone (4), and ethyl acetoacetate affords the salicylate structure 8 instead of the previously reported isophtalate 7. This is the first formation of a salicylate by a double carbonyl condensation of a malondialdehyde moiety ever reported.
Borrell
J I
JI
Grup d'Enginyeria Molecular, Institut Químic de Sarrià, Universitat Ramon Llull, Via Augusta 390, E-08017 Barcelona, Spain. j.i.borrell@iqs.url.edu
Teixidó
J
J
Schuler
E
E
Michelotti
E L
EL
D000090:Acetoacetates / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D009682:Magnetic Resonance Spectroscopy; D008315:Malondialdehyde / Q000737:chemistry*; D008956:Models, Chemical; D010880:Piperidines / Q000737:chemistry; D012459:Salicylates / Q000737:chemistry*
D000090:Acetoacetates; D010880:Piperidines; D012459:Salicylates; D008315:Malondialdehyde; C024840:ethyl acetoacetate