56428-73-0Relevant articles and documents
Reactions of p-Coumaric acid with nitrite: Product isolation and mechanism studies
Torres y Torres, Janelle L.,Rosazza, John P. N.
, p. 1486 - 1492 (2001)
p-Coumaric acid (1) is an abundant plant phenolic acid, a dietary chemoprotectant, and an antioxidant. The chemoprotective properties of I were demonstrated in vitro by its reaction with NaNO2 in H2O over a range of pH values. The reaction pathway of I with nitrite is dependent on pH. 4-Hydroxybenzaldehyde (3, 16%), 1′,4-dihydroxybenzeneacetaldehyde oxime (5, 59%), and 4-hydroxy-1′-oxo-benzeneacetaldehyde aldoxime (7, 26%) and 7-hydroxy-1,2(4H)-benzoxazin-4-one (11, 6%) were each formed at pH 2, whereas 4-(2-oxido-1,2,5-oxadiazol-3-yl)phenol (13) was formed at pH 3 (6%) and pH 7 and 10 (both 1%). Products were isolated and characterized by NMR and MS spectral analyses. Formation of benzoxazinone (11) requires the 4-phenolic functional group and the conjugated propenoic acid side chain of p-coumaric acid. The mechanism for nitrosation at pH 2 was examined by reacting I in H218O/NaNO2.
A deacetylation-diazotation-coupling sequence: Palladium-catalyzed C-C bond formation with acetanilides as formal leaving groups
Schmidt, Bernd,Berger, Rene
supporting information, p. 463 - 476 (2013/05/08)
Acetanilides can be deacetylated and diazotized in situ, and subsequently used in Pd-catalyzed coupling reactions without isolation of the diazonium intermediate. Heck reactions, Suzuki crosscoupling reactions, and a Pd-catalyzed [2+2+1] cycloaddition hav
