[2,3] Fused indoles. Part 2. Synthesis of 1,8-dihydropyrrolo[2,3-b]indoles, and photochemical rearrangement of their 1-allyl derivatives
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 2903-2909
- https://doi.org/10.1039/p19840002903
Abstract
1,8-Dihydropyrrolo[2,3-b]indoles (6) are prepared in three steps from indole-3-carbaldehyde via the azidoacrylates (2). The 2-ester substituent is readily hydrolysed and decarboxylated, whereas attempted reduction leads to bis(pyrroloindolyl)methanes (16). The 1-allyl (21), methylallyl and prenyl derivatives (24a) and (24b) undergo photochemical rearrangement to the 2H-isomers (23), (25a), and (25b) respectively in a reaction typical of pyrroles.Keywords
This publication has 0 references indexed in Scilit: