Petrenko-Kritschenko

In an approach to opioid receptor ligands,diazabicyclononanones were prepared in a double Petrenko-Kritschenko reaction. Diester 76, in the presence of methylamine and aryl aldehydes, was converted to piperidone 77. This was immediately resubmitted to the reaction conditions however, in this iteration formaldehyde replaced the aryl aldehyde component. The outcome of this reaction produced 78 which was further investigated for its use in rheumatoid arthritis. 

Pellini, 118 Pendini, 288 Penfield, 257 Perkin, 60, 61 Peters, 116, 188 Peterson, 341 Petit, 263 Petit, J., 317, 320 Petrenko, 37, 109 Petrenko-Kritschenko, 203 Pfennig, 76 Philipp, 259... 

This reaction is related to the Guareschi-Thorpe Pyridine Synthesis, Chichibabin Pyridine Synthesis, KrOhnke Pyridine Synthesis, and Petrenko-Kritschenko Piperidone Synthesis. 

This reaction was first reported by Petrenko-Kritschenko in 1906. It is the preparation of piperidone via a double Mannich Reaction from acetonedicarboxylic ester, two equivalents of aldehyde, and ammonia (or a primary amine), and is known as the Petrenko-Kritschenko piperidone synthesis. In this reaction, the mixture of reaction components is usually refluxed in an aqueous or alcoholic solution, and the resulting product is difficult to purify. It has been found that the addition of acid to the reaction medium is useful for this reaction.2... 

Other references related to the Petrenko-Kritschenko piperidone synthesis are cited in the literature. ... 

This reaction is related to the Petrenko-Kritschenko Piperidone Synthesis. 

Menschutkin, in a large number of publications (many in Russian), examined the effect of constitution on reaction velocity and concluded that the rate decreases in the order of primary, secondary, and tertiary alcohols. Some exceptions were found by Petrenko-Kritschenko, Bogatsky, and Lubman. Menschutkin s work on the rate of formation of alkylammonium salts was important. He also showed that isomers in which two side-chains are attached to the last but one carbon atom have the lowest boiling-point. ... 

P. Petrenko-Kritschenko and F. Stamoglu, J. Russ. Phys. Chem. 

Petrenko-Kritschenko Piperidone Synthesis Pfau-Plattner Azulene Synthesis Pfitzinger Reaction PFitzner-Moffatt Oxidation... 

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