Intramolecular tetrazine-acryloyl cycloaddition: chemistry and applications.

ABSTRACT: An unprecedented intramolecular [4 + 2] tetrazine-olefin cycloaddition with α,β-unsaturated substrates was discovered. The reaction produces unique coumarin-dihydropyridazine heterocycles that exhibited strong fluorescence with large Stokes shifts and excellent photo- and pH-stability. This property can be used for reaction analysis. The rate of cycloaddition was found to be solvent dependent and was determined using experimental data with a kinetic modeling software (COPASI) as well as DFT calculations (k ₁ = 0.64 ± 0.019 s^-1 and 4.1 s^-1, respectively). The effects of steric and electronic properties of both the tetrazine and α,β-unsaturated carbonyl on the reaction were studied and followed the known trends characteristic of the intermolecular reac

SUBMITTER: Hamsath A 

PROVIDER: S-EPMC9473534 | biostudies-literature | 2022 Sep

REPOSITORIES: biostudies-literature