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

Research output

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.

Original languageEnglish
Pages (from-to)4516-4530
Number of pages15
JournalTetrahedron
Volume75
Issue number33
DOIs
Publication statusPublished - 16 Aug 2019

Fingerprint

Pyridines
Reaction products
Sodium
Alcohols
Derivatives
Temperature
dicyanmethane
pyridine

Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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. In: Tetrahedron. 2019 ; Vol. 75, No. 33. pp. 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.

In: Tetrahedron, Vol. 75, No. 33, 16.08.2019, p. 4516-4530.

Research output

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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DO - 10.1016/j.tet.2019.06.041

M3 - Article

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JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

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