127280-12-0Relevant articles and documents
Lewis Acid Catalyzed Reactions of α,β-Unsaturated N,N-Dimethylhydrazones with 1,4-Benzoquinone. Formation of Indoles by a Novel Oxidative Rearrangement
Echavarren, Antonio M.
, p. 4255 - 4260 (2007/10/02)
The Diels-Alder reaction of quinones and (E)-3-arylpropenal N,N-dimethylhydrazones only proceeds with 1,4-naphthoquinone as the dienophile.The addition of Lewis acids leads to the formation of trans-2,3-dihydrobenzofurans in a highly regioselective process.When propenal N,N-dimethylhydrazones 4 and 5 were allowed to react with 1,4-benzoquinone and boron trifluoride, an unprecedented oxidative rearrangement took place yielding indole-3-carboxaldehyde N,N-dimethylhydrazones 7 and 8, respectively.