Heterocyclic compounds with bridgehead nitrogen atoms. Part III. The formation of cyclopenta[c]quinolizines from 3-α-dimethyl-aminovinylindolizines and dimethyl acetylenedicarboxylate
- 1 January 1966
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society C: Organic
- p. 324-331
- https://doi.org/10.1039/j39660000324
Abstract
2-Alkyl- and 2-aryl-indolizines react with NN-dimethylacetamide, in presence of phosphoryl chloride, to give 3-α-dimethylaminoethylideneindolizinium salts. The enamines derived from the salts by proton-loss react with dimethyl acetylenedicarboxylate in boiling toluene to give dimethyl cyclopenta[c]quinolizinedicarboxylates. The intermediate compounds in this rearrangement have been isolated and the substitution reactions of the cyclopenta[c]quinolizine nucleus have been studied.Keywords
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