Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies

The reaction between dithiomalondianilide (N,N’-diphenyldithiomalondiamide) and alkyl 3-aryl-2-cyanoacrylates in the presence of morpholine in the air atmosphere leads to the formation of alkyl 6-amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]- pyridine-5-carboxylates in 37...

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Главные авторы:	Dotsenko, V. V., Доценко, В. В., Aksenov, N. A., Аксенов, Н. А., Aksenova, I. V., Аксенова, И. В.
Формат:	Статья
Язык:	English
Опубликовано:	2023
Темы:	[1,2]dithiolo[3,4-b]pyridines Herbicide safeners Active methylene thioamides Michael addition Dithiomalondianilide Cyanoacetic esters
Online-ссылка:	https://dspace.ncfu.ru/handle/20.500.12258/23489
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spelling	ir-20.500.12258-234892025-02-10T14:35:37Z Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. [1,2]dithiolo[3,4-b]pyridines Herbicide safeners Active methylene thioamides Michael addition Dithiomalondianilide Cyanoacetic esters The reaction between dithiomalondianilide (N,N’-diphenyldithiomalondiamide) and alkyl 3-aryl-2-cyanoacrylates in the presence of morpholine in the air atmosphere leads to the formation of alkyl 6-amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]- pyridine-5-carboxylates in 37–72% yields. The same compounds were prepared in 23–65% yields by ternarycondensation of aromatic aldehydes, ethyl(methyl) cyanoacetate and dithiomalondianilide. The reaction mechanism is discussed. The structure of ethyl 6-amino-4-(4-methoxyphenyl)-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylate was confirmed by X-ray crystallography. Two of the prepared compounds showed a moderate growth-stimulating effect on sunflower seedlings. Three of the new compounds were recognized as strong herbicide safeners with respect to herbicide 2,4-D in the laboratory and field experiments on sunflower. 2023-05-24T09:55:55Z 2023-05-24T09:55:55Z 2023 Статья Dotsenko, V.V., Sinotsko, A.E., Strelkov, V.D., Varzieva, E.A., Russkikh, A.A., Levchenko, A.G., Temerdashev, A.Z., Aksenov, N.A., Aksenova, I.V. Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies // Molecules. - 2023. - 28(2), art. no. 609. - DOI: 10.3390/molecules28020609. http://hdl.handle.net/20.500.12258/23489 en Molecules application/pdf application/pdf
institution	СКФУ
collection	Репозиторий
language	English
topic	[1,2]dithiolo[3,4-b]pyridines Herbicide safeners Active methylene thioamides Michael addition Dithiomalondianilide Cyanoacetic esters
spellingShingle	[1,2]dithiolo[3,4-b]pyridines Herbicide safeners Active methylene thioamides Michael addition Dithiomalondianilide Cyanoacetic esters Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В. Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies
description	The reaction between dithiomalondianilide (N,N’-diphenyldithiomalondiamide) and alkyl 3-aryl-2-cyanoacrylates in the presence of morpholine in the air atmosphere leads to the formation of alkyl 6-amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]- pyridine-5-carboxylates in 37–72% yields. The same compounds were prepared in 23–65% yields by ternarycondensation of aromatic aldehydes, ethyl(methyl) cyanoacetate and dithiomalondianilide. The reaction mechanism is discussed. The structure of ethyl 6-amino-4-(4-methoxyphenyl)-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylate was confirmed by X-ray crystallography. Two of the prepared compounds showed a moderate growth-stimulating effect on sunflower seedlings. Three of the new compounds were recognized as strong herbicide safeners with respect to herbicide 2,4-D in the laboratory and field experiments on sunflower.
format	Статья
author	Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_facet	Dotsenko, V. V. Доценко, В. В. Aksenov, N. A. Аксенов, Н. А. Aksenova, I. V. Аксенова, И. В.
author_sort	Dotsenko, V. V.
title	Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies
title_short	Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies
title_full	Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies
title_fullStr	Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies
title_full_unstemmed	Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies
title_sort	alkyl 4-aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3h-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: synthesis and agrochemical studies
publishDate	2023
url	https://dspace.ncfu.ru/handle/20.500.12258/23489
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Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies

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