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RESEARCH PRODUCT
The reactivity of 2-vinylindoles with dimethyl acetylenedicarboxylate
Teresa Aznar SalientePilar Martinez FresnedaR. Alan JonesJosé Sepúlveda Arquessubject
Indole testDimethyl acetylenedicarboxylateSteric effectsDieneChemistryStereochemistryOrganic ChemistryBiochemistryMedicinal chemistryCycloadditionchemistry.chemical_compoundDrug DiscoveryMichael reactionReactivity (chemistry)Cope rearrangementdescription
Abstract The overall rates of reaction of 1-substltuted-1- (1-methyl-2-indolyl)ethenes with dimethyl acetylenedicarboxylate are considerably lower than those of the corresponding 2-vinyl- pyrroles. Steric interaction between the N-methyl group on the indole ring and the 1-substituent on the ethenyl group prevents the diene system adopting a coplanar cisoid configuration and, thereby, inhibits the π4 + π2 cycloaddition reaction of the system with dimethyl acetylenedicarboxylate. Under such conditions, the indolylethene preferentially undergoes a Michael addition reaction at the 3-position. The π4 + π2 cycloaddition reaction is promoted at elevated temperatures. No evidence was found for a Cope rearrangement of the Michael adducts to give the dihydrocarbazole.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1984-01-01 | Tetrahedron |