6533b834fe1ef96bd129d5fa
RESEARCH PRODUCT
Reactions of the hydrofluoroborate salts of open-chain analogues of Reissert compounds with some α,β-ethylenic esters
Marek M. KubickiBernard LaudeSandrine PerrinKarin MonnierOlivier Blacquesubject
10120 Department of Chemistrychemistry.chemical_classificationOrganic ChemistryImineSalt (chemistry)Azomethine ylideSequence (biology)Medicinal chemistryCycloadditionchemistry.chemical_compoundchemistry540 Chemistry13-Dipolar cycloadditionEthyl acrylatePhysical and Theoretical Chemistry1606 Physical and Theoretical ChemistryDerivative (chemistry)1605 Organic Chemistrydescription
The reaction of the hydrofluoroborate salt of an open-chain analogue of a Reissert compound with some α,β-ethylenic esters does not give a [4 + 2] cycloadduct, as previously described in the case of ethyl acrylate. The reaction starts with a 1,3-dipolar cycloaddition of a munchnone imine 5c, d. The [3 + 2] cycloadducts 13 evolve via a rearrangement–condensation sequence to give a substituted 2-pyridone derivative 18 or 19. The proposed mechanism has been verified by the isolation and structural X-ray analysis of some compounds of the reaction sequence.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1999-01-01 |