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RESEARCH PRODUCT
Diels-alder reactions of methyl- and π-acceptor-substituted 2-vinylindoles with dimethyl acetylenedicarboxylate and tetracyanoethylene: Novel functionalized carbazoles
Manfred EitelUlf Pindursubject
Dimethyl acetylenedicarboxylatechemistry.chemical_compoundchemistryOrganic ChemistryDiels alderDehydrogenationNuclear Overhauser effectTetracyanoethyleneAcceptorMedicinal chemistryEne reactiondescription
The Diels-Alder reactions of the 2-vinylindoles 1a-1d, which are now readily accessible, with dimethyl acetylenedicarboxylate and tetracyanoethylene give rise to the novel 1,2-dihydro- and 1,2,3,4-tetrahydrocarbazoles 2, 4, and 5 as well as the fully aromatized carbazoles 3. With regard to the product spectrum, the mechanistic rationale comprises a Diels-Alder step, formal 1,3-hydrogen shift, ene reaction, and dehydrogenation. Conformational aspects of the 1,2-dihydrocarbazoles 2b and 2c are also discussed.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1991-06-01 | Journal of Heterocyclic Chemistry |