4-(2′-Hydroxyphenylmethylene)-2-phenyloxazol-5(4H)-one: a comedy of errors

Alcohol Uncaging with Fluorescence Reporting: Evaluation of o-Acetoxyphenyl Methyloxazolone Precursors

“…In parallel to the development of the o -hydroxy cinnamate series, we considered another cinnamate series relying on the o -hydroxyphenyl oxazolone precursor. During the synthesis of those cinnamates, Cornforth et al noticed that, upon heating, isomerization occurs around their trisubstituted double bond, leading to the formation of a coumarin . Such a reaction could also be triggered by light, as later noted .…”

A synthesized GFP analogue emits via a hydrogen-bonding system

“…Such a configuration has also been reported in dozens of reactions. 14 o-HBMO showed a strong fluorescence emission at 390 nm (Fig. 1) in aqueous solution.…”

“…o-HBMO analogues are notoriously unstable and tend to rearrange to coumarin-like isomers. 14 To reveal the structure of o-HBMO under our experimental conditions, IR and NMR investigations were carried out. The results indicated that o-HBMO adopted the configuration as shown in Scheme 1 in water (see ESIw) instead of a coumarin-like structure.…”

Sir John Cornforth Ac Cbe Frs: His Synthetic Work

“…In the course of this study, he uncovered a novel thermal isomerisation of an oxazole to a pyrone 15. This led Cornforth to re-examine 36 the condensation of salicylaldehyde with hippuric acid, a reaction which would be part of the conventional synthesis of an amino acid. There were 18 reports in the literature of the formation of the alleged oxazolone 16 in this reaction, all of which Cornforth showed to be erroneous ('the comedy of errors').…”