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Open AccessProceedings

Synthesis of 4-(1,3,5-Thiadiazinan-2-ylidene)-2-(3,4- dihydro-2H-1,3,5-thiadiazin-6-yl)pent-2-enedinitriles

1
Department of Chemistry and High Technologies, Kuban State University, 149 Stavropolskaya str, Krasnodar 350040, Russia
2
ChemEx Lab, Vladimir Dal’ Lugansk National University, 20A/7 Molodezhny, Lugansk 91034, Russia
3
Department of Chemistry, North Caucasus Federal University, 1a Pushkin St., 355009 Stavropol, Russia
4
The Federal State Unitary Enterprise “Institute of Chemical Reagents and High Purity Chemical Substances” of National Research Centre “Kurchatov Institute”, 3 Bogorodsky Val, Moscow 107076, Russia
*
Author to whom correspondence should be addressed.
Presented at the 22nd International Electronic Conference on Synthetic Organic Chemistry, 15 November–15 December 2018; Available Online: https://sciforum.net/conference/ecsoc-22
Proceedings 2019, 9(1), 24; https://doi.org/10.3390/ecsoc-22-05681
Published: 14 November 2018
(This article belongs to the Proceedings of International Electronic Conference on Synthetic Organic Chemistry)
The reaction of cyanothioacetamide with diethyl ethoxymethylenemalonate in the presence of triethylamine in hot EtOH proceeds non-selectively and leads to the formation of a mixture of triethylammonium 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate (minor) and triethylammonium 3-cyano-5-ethoxycarbonyl-6-oxo-1Н-pyridine-2-thiolate (major). Upon treatment with primary amines and 37% aqueous HCHO in boiling aqueous ethanol, the reaction product affords only 4-(1,3,5-thiadiazinan-2-ylidene)-2-(3,4-dihydro-2H-1,3,5-thiadiazin- 6-yl)pent-2-enedinitrile derivatives, instead of the expected pyrido[2,1-b][1,3,5]thiadiazines. Triethylammonium 3-cyano-5-ethoxycarbonyl-6-oxo-1Н-pyridine-2-thiolate does not react under these conditions. The structure of the resulted products was confirmed by means of NMR, IR spectroscopy, and LCMS. The mechanism of the formation of the products is discussed.
Keywords: cyanothioacetamide; diethyl ethoxymethylenemalonate; aminomethylation; Mannich reaction; 1,3,5-thiadiazines cyanothioacetamide; diethyl ethoxymethylenemalonate; aminomethylation; Mannich reaction; 1,3,5-thiadiazines
MDPI and ACS Style

Dotsenko, V.V.; Chigorina, E.A.; Krivokolysko, S.G. Synthesis of 4-(1,3,5-Thiadiazinan-2-ylidene)-2-(3,4- dihydro-2H-1,3,5-thiadiazin-6-yl)pent-2-enedinitriles. Proceedings 2019, 9, 24.

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