Mannich-type reaction of tetrahydropyridine-2-thiolates with primary amines and &alpha;-substituted propanals

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

Published: 08 November 2016 by MDPI in The 20th International Electronic Conference on Synthetic Organic Chemistry session General Organic Synthesis

https://doi.org/10.3390/ecsoc-20-a061

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

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