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

被引：8

作者：

Kuznetcova, Anastasiya, V ^{[1
]}

Odin, Ivan S. ^{[2
]}

Golovanov, Alexander A. ^{[3
]}

Grigorev, Iakov M. ^{[4
]}

Vasilyev, Aleksander V. ^{[1
,5
]}

机构：

[1] St Petersburg State Univ, Inst Chem, Dept Organ Chem, Univ Skaya Nab 7-9, St Petersburg 199034, Russia

[2] Togliatti State Univ, Res Lab Organ Synth & Anal Them SP Korshunov 13, Belorusskaya Ul 14, Tolyatti 445667, Russia

[3] Togliatti State Univ, Dept Chem Chem Proc & Technol, Belorusskaya Ul 14, Tolyatti 445667, Russia

[4] St Petersburg State Univ, Educ Res Ctr Chem Res Pk, Univ Skiy Pr 26, St Petersburg 198504, Petrodvoretz, Russia

[5] St Petersburg State Forest Tech Univ, Dept Chem, Inst Sky 5, St Petersburg 194021, Russia

来源：

TETRAHEDRON | 2019年 / 75卷 / 33期

基金：

俄罗斯科学基金会;

关键词：

Conjugated enynones; Pyridines; Nicotinonitriles; Reaction mechanism; Fluorescence; FACILE SYNTHESIS; FLUORESCENCE; NICOTINONITRILES; CYCLIZATION;

D O I：

10.1016/j.tet.2019.06.041

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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. (C) 2019 Elsevier Ltd. All rights reserved.

引用

页码：4516 / 4530

页数：15

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