Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides: Complex reaction mechanism of the formation of pyridine derivatives

Anastasiya V. Kuznetcova, Ivan S. Odin, Alexander A. Golovanov, Iakov M. Grigorev, Aleksander V. Vasilyev

Результат исследований: Научные публикации в периодических изданияхстатья

Выдержка

Reaction of conjugated enynones,1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile and sodium alkoxides in the corresponding alcohols at room temperature for 3–23 h results in the formation of two types of compounds (E)-/(Z)-6-aryl-4-(2-arylethenyl)-2-alkoxypyridine-3-carbonitriles (substituted nicotinonitriles), as the major reaction products in yields up to ca. 40–80%, and 6-aryl-4-arylethynyl-2-alkoxypyridines, as the minor reaction products in yields of 5–17%. Plausible mechanism of this complex and multistep reaction is discussed. The obtained pyridines possess fluorescent properties.

Язык оригиналаанглийский
Страницы (с-по)4516-4530
Число страниц15
ЖурналTetrahedron
Том75
Номер выпуска33
DOI
СостояниеОпубликовано - 16 авг 2019

Отпечаток

Pyridines
Reaction products
Sodium
Alcohols
Derivatives
Temperature
dicyanmethane
pyridine

Предметные области Scopus

  • Биохимия
  • Поиск новых лекарств
  • Органическая химия

Цитировать

Kuznetcova, Anastasiya V. ; Odin, Ivan S. ; Golovanov, Alexander A. ; Grigorev, Iakov M. ; Vasilyev, Aleksander V. / Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides : Complex reaction mechanism of the formation of pyridine derivatives. В: Tetrahedron. 2019 ; Том 75, № 33. стр. 4516-4530.
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abstract = "Reaction of conjugated enynones,1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile and sodium alkoxides in the corresponding alcohols at room temperature for 3–23 h results in the formation of two types of compounds (E)-/(Z)-6-aryl-4-(2-arylethenyl)-2-alkoxypyridine-3-carbonitriles (substituted nicotinonitriles), as the major reaction products in yields up to ca. 40–80{\%}, and 6-aryl-4-arylethynyl-2-alkoxypyridines, as the minor reaction products in yields of 5–17{\%}. Plausible mechanism of this complex and multistep reaction is discussed. The obtained pyridines possess fluorescent properties.",
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Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides : Complex reaction mechanism of the formation of pyridine derivatives. / Kuznetcova, Anastasiya V.; Odin, Ivan S.; Golovanov, Alexander A.; Grigorev, Iakov M.; Vasilyev, Aleksander V.

В: Tetrahedron, Том 75, № 33, 16.08.2019, стр. 4516-4530.

Результат исследований: Научные публикации в периодических изданияхстатья

TY - JOUR

T1 - Multicomponent reaction of conjugated enynones with malononitrile and sodium alkoxides

T2 - Complex reaction mechanism of the formation of pyridine derivatives

AU - Kuznetcova, Anastasiya V.

AU - Odin, Ivan S.

AU - Golovanov, Alexander A.

AU - Grigorev, Iakov M.

AU - Vasilyev, Aleksander V.

PY - 2019/8/16

Y1 - 2019/8/16

N2 - Reaction of conjugated enynones,1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile and sodium alkoxides in the corresponding alcohols at room temperature for 3–23 h results in the formation of two types of compounds (E)-/(Z)-6-aryl-4-(2-arylethenyl)-2-alkoxypyridine-3-carbonitriles (substituted nicotinonitriles), as the major reaction products in yields up to ca. 40–80%, and 6-aryl-4-arylethynyl-2-alkoxypyridines, as the minor reaction products in yields of 5–17%. Plausible mechanism of this complex and multistep reaction is discussed. The obtained pyridines possess fluorescent properties.

AB - Reaction of conjugated enynones,1,5-diarylpent-2-en-4-yn-1-ones, with malononitrile and sodium alkoxides in the corresponding alcohols at room temperature for 3–23 h results in the formation of two types of compounds (E)-/(Z)-6-aryl-4-(2-arylethenyl)-2-alkoxypyridine-3-carbonitriles (substituted nicotinonitriles), as the major reaction products in yields up to ca. 40–80%, and 6-aryl-4-arylethynyl-2-alkoxypyridines, as the minor reaction products in yields of 5–17%. Plausible mechanism of this complex and multistep reaction is discussed. The obtained pyridines possess fluorescent properties.

KW - Conjugated enynones

KW - Fluorescence

KW - Nicotinonitriles

KW - Pyridines

KW - Reaction mechanism

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U2 - 10.1016/j.tet.2019.06.041

DO - 10.1016/j.tet.2019.06.041

M3 - Article

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VL - 75

SP - 4516

EP - 4530

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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