A New Synthetic Approach to Pyrrolo[3,4-a]indolizines

2-Pyridineacetonitrile was found to react with 1,3-dichloro-2-propanone in the presence of chlorotrimethylsilane yielding 2-chloromethyl-1-indolizinecarbonitrile. The chlorine atom in the prepd. indolizine was replaced by various nucleophiles including substituted anilines. Treatment of 2-(arylamino)methyl-1-indolizinecarbonitriles with hydrochloric acid resulted in 2-aryl-2,3-dihydro-1H-pyrrolo[3,4-a]indolizine-1-iminium chlorides.

Tereshchenko A. D.; Sysoiev D. A.; Tverdokhlebov A. V.; Tolmachev A. A.
Synthesis 2006, 02, 349-353
DOI: 10.1055/s-2005-918510