EventsThe 20th International Electronic Conference on Synthetic Organic Chemistry
Event submissions
Published
with-doi10.3390/ecsoc-20-a061
This submission belongs to the session a. General Organic Synthesis of the event The 20th International Electronic Conference on Synthetic Organic Chemistry
Published date
08 Nov, 2016
Citation
Victor V. Dotsenko, Elena A. Chigorina, Ivan S. Bushmarinov, Alexander S. Goloveshkin, Sergey G. Krivokolysko, Mannich-type reaction of tetrahydropyridine-2-thiolates with primary amines and α-substituted propanals, in Proceedings of The 20th International Electronic Conference on Synthetic Organic Chemistry, 1 November–30 November 2016, MDPI: Basel, Switzerland, doi: 10.3390/ecsoc-20-a061
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Mannich-type reaction of tetrahydropyridine-2-thiolates with primary amines and α-substituted propanals

Victor V. Dotsenko 1,2,3
Elena A. Chigorina 4
Ivan S. Bushmarinov 5
Alexander S. Goloveshkin 5
Sergey G. Krivokolysko 2,6
1. Kuban State University, 149 Stavropolskaya Str., Krasnodar 350040, Russian Federation
2. ChemEx Lab, Vladimir Dal’ Lugansk National University, Lugansk, 91034 Russia.
3. North-Caucasus Federal University, 1 Pushkina St., 355009 Stavropol, Russian Federation
4. Federal State Unitary Enterprise «Research Institute of Chemical Reactants and Ultrapure Compounds (IREA)», 3 Bogorodsky Shaft, Moscow 107076, Russia
5. A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 Vavilova Str., Moscow 119991, Russia
6. Lugansk State Medical University, 1-g 50 years of Lugansk Defence, Lugansk 91045, Russia
Abstract

The Mannich-type reaction of N-methylmorpholinium 4-aryl-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates with 2-R-propanals (ocean propanal, isobutyraldehyde) and primary aromatic amines afforded 7-aryl-2-R-2-methyl-3-arylamino-5-oxo-2,3,6,7-tetrahydro-5Н-thiazolo[3,2-a]pyridine-8-carbonitriles in modest yields; the structure of a key compound was confirmed by X-ray crystal structure analysis. The mechanism of the reaction is discussed.

Keywords
Pyridine-2-thiolates
aminomethylation
X-ray studies
bis(pyrid-2-yl)disulfides
Mannich reaction
thiazolopyridines
heterocyclization
Manuscript
ECSOC 20 abstract 1 isobutyral ocean propanal thiazolopyridines.pdf
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