Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result

The reaction of cyanothioacetamide with ethoxymethylenemalonate and triethylamine in ethanol upon heating is non-selective and leads to the formation of a mixture of triethylammonium 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and triethylammonium 6-oxo-3-cyano-5-ethoxycarbonyl-1H-pyr...

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Huvudupphovsmän:	Dotsenko, V. V., Доценко, В. В.
Materialtyp:	Статья
Språk:	English
Publicerad:	Pleiades Publishing 2020
Ämnen:	1,3,5-thiadiazines Aminomethylation Cyanothioacetamide Diethyl ethoxymethylenemalonate Mannich reaction
Länkar:	https://dspace.ncfu.ru/handle/20.500.12258/12161
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id	ir-20.500.12258-12161
record_format	dspace
spelling	ir-20.500.12258-121612020-07-29T09:24:37Z Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result Dotsenko, V. V. Доценко, В. В. 1,3,5-thiadiazines Aminomethylation Cyanothioacetamide Diethyl ethoxymethylenemalonate Mannich reaction The reaction of cyanothioacetamide with ethoxymethylenemalonate and triethylamine in ethanol upon heating is non-selective and leads to the formation of a mixture of triethylammonium 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and triethylammonium 6-oxo-3-cyano-5-ethoxycarbonyl-1H-pyridin-2-thiolate with a predominance of the latter. When treating with primary amines and 37% formalin in boiling aqueous alcohol, the reaction product gives only 4-(1,3,5-thiadiazinan-2-ylidene)-2-(3,4-dihydro-2H-1,3,5-thiadiazin-6-yl)pent-2-enedinitrile instead of the expected pyrido[2,1-b][1,3,5]thiadiazine derivatives. Triethylammonium 6-oxo-3-cyano-5-ethoxycarbonyl-1H-pyridin-2-thiolate does not react under these conditions 2020-06-30T12:40:29Z 2020-06-30T12:40:29Z 2020 Статья Dotsenko, V.V., Krivokolysko, S.G., Chigorina, E.A. Reaction of Ethoxymethylenemalonate with Cyanothioacetamide in the Presence of Triethylamine: Formation of 1,5-Diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and Unexpected Aminomethylation Result // Russian Journal of General Chemistry. - 2020. - Volume 90. - Issue 4. - Pages 590-596 http://hdl.handle.net/20.500.12258/12161 en Russian Journal of General Chemistry application/pdf application/pdf Pleiades Publishing
institution	СКФУ
collection	Репозиторий
language	English
topic	1,3,5-thiadiazines Aminomethylation Cyanothioacetamide Diethyl ethoxymethylenemalonate Mannich reaction
spellingShingle	1,3,5-thiadiazines Aminomethylation Cyanothioacetamide Diethyl ethoxymethylenemalonate Mannich reaction Dotsenko, V. V. Доценко, В. В. Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result
description	The reaction of cyanothioacetamide with ethoxymethylenemalonate and triethylamine in ethanol upon heating is non-selective and leads to the formation of a mixture of triethylammonium 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and triethylammonium 6-oxo-3-cyano-5-ethoxycarbonyl-1H-pyridin-2-thiolate with a predominance of the latter. When treating with primary amines and 37% formalin in boiling aqueous alcohol, the reaction product gives only 4-(1,3,5-thiadiazinan-2-ylidene)-2-(3,4-dihydro-2H-1,3,5-thiadiazin-6-yl)pent-2-enedinitrile instead of the expected pyrido[2,1-b][1,3,5]thiadiazine derivatives. Triethylammonium 6-oxo-3-cyano-5-ethoxycarbonyl-1H-pyridin-2-thiolate does not react under these conditions
format	Статья
author	Dotsenko, V. V. Доценко, В. В.
author_facet	Dotsenko, V. V. Доценко, В. В.
author_sort	Dotsenko, V. V.
title	Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result
title_short	Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result
title_full	Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result
title_fullStr	Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result
title_full_unstemmed	Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result
title_sort	reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result
publisher	Pleiades Publishing
publishDate	2020
url	https://dspace.ncfu.ru/handle/20.500.12258/12161
work_keys_str_mv	AT dotsenkovv reactionofethoxymethylenemalonatewithcyanothioacetamideinthepresenceoftriethylamineformationof15diamino24dicyano5thioxopenta13diene1thiolateandunexpectedaminomethylationresult AT docenkovv reactionofethoxymethylenemalonatewithcyanothioacetamideinthepresenceoftriethylamineformationof15diamino24dicyano5thioxopenta13diene1thiolateandunexpectedaminomethylationresult
_version_	1760599581350952960

Reaction of ethoxymethylenemalonate with cyanothioacetamide in the presence of triethylamine: formation of 1,5-diamino-2,4-dicyano-5-thioxopenta-1,3-diene-1-thiolate and unexpected aminomethylation result

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