Studies in the synthesis of camptothecin. An efficient synthesis of 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline
- 1 January 1971
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- Vol. 21, 3551-3554
- https://doi.org/10.1039/j39710003551
Abstract
An efficient regioselective synthesis of 2,3-dihydro-1H-pyrrolo[3,4-b]quinoline (3), a key intermediate in the synthesis of camptothecin, has been developed. The synthesis, which has been extended to a number of analogues, involves an acid-catalysed Friedländer condensation in the absence of a solvent. Base-catalysed condensation was shown to lead predominantly to the isomeric 2,3-dihydro-1H-pyrrolo[3,2-b]quinoline (10). The relative stabilities of the enols and enolates derived from N-acetyl-3-pyrrolidone and ethyl 3-oxopyrrolidine-1-carboxylate, intermediates in the synthesis of compounds (3) and (10), are discussed.Keywords
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