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Communication | Special issue | Vol 84, No. 1, 2012, pp.265-274
Published online, 22nd April, 2011
DOI: 10.3987/COM-11-S(P)5
Mechanistic Investigations of the Cyclocondensation Step of the Knorr Pyrrole Synthesis

Scott A. Snyder,* Ferenc Kontes, and Adel M. ElSohly

*Department of Chemistry, Columbia University, 3000 Broadway, New York, NY 10027, U.S.A.


A mechanistic investigation of the cyclocondensation step of the Knorr pyrrole synthesis of pyrrolo[2,1,5-cd]indolizidines is reported. Kinetic isotope effect measurements suggest the participation of two protic solvent molecules in a rate-determining ketone protonation prior to cyclization and dehydration.