Nitrene. Part XIII. Novel conversion of 2-nitrophenyl substituted butyrolactones into indoles with triethyl phosphite
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 861-863
- https://doi.org/10.1039/p19740000861
Abstract
Reductive cyclization of α-(2-hydroxyethyl)-β-methoxy-o-nitrocinnamic acid γ-lactone (4) with triethyl phosphite produced 3,4-dihydro-5-methoxy[1,3]oxazino[3,4-a]indol-1-one (6), a new heterocyclic ring system. Reduction of 2-o-nitrobenzoyl-γ-butyrolactone (3) yielded 4,5-dihydro-1′H-spiro[furan-3,2′-indole]-2,3′-dione (8) as the major product, in addition to a trace amount of the 5-ethoxy-analogue of (6). Lactone (8) was hydrolysed and decarboxylated to give 1,2-dihydro-2-(2-hydroxyethyl)indol-3-one (9). These results provide a route to novel reactive heterocyclic lactones.Keywords
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