EventsThe 16th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-16-01090
This submission belongs to the session a. General Organic Synthesis of the event The 16th International Electronic Conference on Synthetic Organic Chemistry
Published date
30 Oct, 2012
Citation
Victor V. Dotsenko, Elena A. Chigorina, Synthesis of New Bispidine-type Compounds Starting from Guareshi Imides, in Proceedings of The 16th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2012, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-16-01090
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Synthesis of New Bispidine-type Compounds Starting from Guareshi Imides

Elena A. Chigorina 1
Victor V. Dotsenko 2
1. ChemDiv Research Institute (CDRI), Rabochaya St. 2-a, Moscow Region, Khimki
2. ChemEx Laboratory, Vladimir Dal' East Ukrainian Nationa University, Molodezhny 20A, Lugansk
Abstract
The reaction of 1-cyanoacetyl-3,5-dimethylpyrazole with 2-cyanoacrylamides in the presence of triethylamine leads to triethylammonium 3,5-dicyano-6-oxo-1,4,5,6-tetrahydropyridine-2-olates (salts of Guareshi imides). The latter reacted with primary amines RNH2 and excessive HCHO to give triethylammonium salts of 7-R-2,4-dioxo-3,7-diazabicyclo[3.3.1]nonane-1,5-dicarbonitriles. When treated with HCl or alkyl halides, the salts afforded corresponding 3-R- or 3,7-disubstituted bispidines.
Keywords
cyanoacetylpyrazole
Guareshi imides
diazabicyclononanes
bispidines,Mannich reaction
Kinetic resolution of Pent-4-ene-1,3-diol by Pd(II)-catalysed Oxycarbonylation in Ionic Liquids
Synthesis and Alkylation of 5-Benzoyl-3-cyano-6-phenylpyridine-2(1H)-thione