Journal of the Chemical Society. Perkin transactions I p. 1319 - 1323 (1980)
Update date:2022-07-30
Topics:
Jessep, Michael A.
Leaver, Derek
3H-Pyrrolizine reacts with NN-dimethylformamide and phosphoryl chloride to give a 3-(NN-dimethylaminomethylene)-3H,5H-pyrrolizinium salt (2), isolated as the perchlorate, which can be further converted, with NN-dimethylthioformamide and acetic anhydride, into 3,5-bis-(NN-dimethylaminomethylene)-3H,5H-pyrrolizinium perchlorate (8).The conjugate base of the salt (2) reacts with dimethyl but-2-yne-1,4-dioate to give dimethyl pyrrolo<2,1,5-cd>indolizine-5,6-dicarboxylate.The salt (8) reacts with nitromethane, in the presence of base, to give 6-nitropyrrolo<2,1,5-cd>indolizine (9a) and with ammonia to give pyrazino<2,1,6-cd>pyrrolizine (10a).Electrophilic substitution reactions of (9a) and (10a), and nucleophilic substitution of (10a), are described.
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