1,3-Dimethylindole reacts with dimethylacetylenedicarboxylate in the presence of BF3–Et2O to give the benzazepine (3; R ![[double bond, length half m-dash]](https://www.rsc.org/images/entities/char_e006.gif)
H), the maleate (4), and the fumarate (5); 1,2,3-trimethylindole under similar conditions reacted to give the benzazepine (3, R Me) and the dienone (6).
F. Fried, J. B. Taylor and R. Westwood, J. Chem. Soc. D, 1971, 1226 DOI: 10.1039/C29710001226
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