27884-36-2Relevant academic research and scientific papers
Heterocyclic Compounds with Bridgehead Nitrogen Atoms. Part 7. The Synthesis of Pyrroloindolizines (Cyclazines) and Pyrazinopyrrolizines (6-Azacyclazines) from 3H-Pyrrolizine
Jessep, Michael A.,Leaver, Derek
, p. 1319 - 1323 (1980)
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 pyrroloindolizine-5,6-dicarboxylate.The salt (8) reacts with nitromethane, in the presence of base, to give 6-nitropyrroloindolizine (9a) and with ammonia to give pyrazinopyrrolizine (10a).Electrophilic substitution reactions of (9a) and (10a), and nucleophilic substitution of (10a), are described.
