107209-24-5Relevant articles and documents
Synthesis and Thermal Rearrangement of Allylic 3,5,6-Trimethyl-2-Pyrazinylacetates: A Heterocyclic Carroll Rearrangement
Podraza, Kenneth F.
, p. 581 - 583 (2007/10/02)
The synthesis of allylic 3,5,6-trimethyl-2-pyrazinylacetates 2-4 has been achieved by the reaction of 3,5,6-trimethyl-2-pyrazinylacetic acid lithium salt (1) with phenyl dichlorophosphate followed by addition of the allylic alcohol.On thermolysis, the allylic β-heteroaromatic esters underwent a rearrangement, analogous to the Carroll rearrangement, to generate the corresponding γ,δ-unsaturated heteroaromatic compound.The configuration of the double bond formed in the product was the E-isomer.The rate of the rearrangement was dependent on the substitution pattern of the allylic portion of the molecule with 4>2>3.The ester enolate version of the heterocyclic Carroll rearrangement was investigated with 2, however these conditions did not promote the rearrangement.