136558-72-0Relevant articles and documents
Diels-Alder Reactions of Methyl- and ?-Acceptor-Substituted 2-Vinylindoles with Dimethyl Acetylenedicarboxylate and Tetracyanoethylene: Novel Functionalized Carbazoles
Pindur, Ulf,Eitel, Manfred
, p. 951 - 954 (2007/10/02)
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.