EventsThe 17th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-17-a045
This submission belongs to the session a. General Organic Synthesis of the event The 17th International Electronic Conference on Synthetic Organic Chemistry
Published date
31 Oct, 2013
Citation
Elena A. Chigorina, Victor V. Dotsenko, The Michael-type Addition of 1-Cyanoacetyl-3,5-dimethylpyrazole to Arylmethylenecyanoacetamides, in Proceedings of The 17th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2013, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-17-a045
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The Michael-type Addition of 1-Cyanoacetyl-3,5-dimethylpyrazole to Arylmethylenecyanoacetamides

Elena A. Chigorina 1
Victor V. Dotsenko 2,3,4
1. Federal State Unitary Enterprise «Research Institute of Chemical Reactants and Ultrapure Compounds (IREA)», 3 Bogorodsky Shaft, Moscow 107076, Russia
2. Kuban State University, 149 Stavropolskaya Str., Krasnodar 350040, Russian Federation
3. ChemEx Lab, Vladimir Dal’ Lugansk National University, Lugansk, 91034 Russia.
4. North-Caucasus Federal University, 1 Pushkina St., 355009 Stavropol, Russian Federation
Abstract
Abstract: The Et3N-promoted reaction of (E)-3-aryl-2-cyanoacrylamides (arylmethylenecyanoacetamides) with 1-cyanoacetyl-3,5-dimethylpyrazole was thoroughly studied. It was found that either triethylammonium 4-aryl-3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-olates 1 (salts of Guareschi imides) or their oxidation products – triethylammonium 4-aryl-3,5-dicyano-6-oxo-1,6-dihydropyridine-2-olates 2 were formed, depending on the nature of substituents in the 3-aryl fragment of starting acrylamides. Thus, when Ar = ortho-, meta-substituted phenyl or hetaryl such as 2-furyl, 3-thienyl etc., only Guareschi imides salts 1 were obtained in good to excellent yields. In the case of para-substituted or unsubstituted phenyl, pyridine-2-olates 2 were isolated as major products due to fast oxidation of Guareschi intermediates. The influence of reaction conditions and the nature of the base on the structure of final products is discussed.
Keywords
Manuscript
ecsoc17 1.pdf
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