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Z. Naturforsch. 2012,
67b, 1151 – 1158
doi:10.5560/ZNB.2012-0230
One-pot Synthesis of 3-Aryl-substituted 1-Hydroxy-2-acylindolizines
1 Institut für Anorganische und Analytische Chemie, Friedrich-Schiller-Universität Jena, Humboldtstraße 8, 07743 Jena, Germany
2 Institut für Chemie, Technische Universität Berlin, Straße des 17. Juni 135, 10623 Berlin, Germany
Reprint requests to Prof. M. Westerhausen. Fax: +49 3641 948102. E-mail:
m.we@uni-jena.de
Received August 30, 2012 / published online November 12, 2012
Dedicated to Professor Rainer Beckert on the occasion of his 60th birthday
A new method for the formation of C–C bonds in a one-pot synthesis of 1-hydroxy-2-acyl-3-arylindolizines (acyl: 2-pyridylformyl, thienylformyl; aryl: phenyl, pyridyl, thienyl) from the reaction of 1,3-diketones with aldehydes has been evaluated. X-Ray diffraction studies of single crystals have provided structural information about the so-formed indolizines. In the crystalline state, the hydroxyl units form intra- or intermolecular hydrogen bonds to the acyl functionalities. The color of these indolizines depends on the pH value of the solvent.
Key words: Aza-Nazarov Cyclization, Fused-ring Systems, Indolizines, Multi-component Reaction, Nitrogen Heterocycles