3-(phenylethynyl)quinoxaline-2-carbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 3-(phenylethynyl)quinoxaline-2-carbonitrile
• 英文别名: 3-(Phenylethynyl)quinoxaline-2-carbonitrile；3-(2-phenylethynyl)quinoxaline-2-carbonitrile
• 化学式: C₁₇H₉N₃
• 分子量: 255.279
• InChiKey: BPIHCQNKKAOVDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  49.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-(phenylethynyl)quinoxaline-2-carbonitrile 在 氨 、 potassium carbonate 、 氯化铵 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以90%的产率得到(Z)-3-(2-amino-2-phenylvinyl)quinoxaline-2-carbonitrile
  参考文献：
  名称：

  Nucleophilic cyclization of 3-alkynylquinoxaline-2-carbonitriles into pyrido[3,4-b]quinoxalines

  摘要：

  3-Alkynylquinoxaline-2-carbonitriles have been synthesized from 3-chloroquinoxaline-2-carbonitrile via the Sonogashira reaction. Treatment of 3-alkynylquinoxaline-2-carbonitriles with an alkylamine or ammonia has been shown to produce stable enamines, e.g., (Z)-3-(2-aryl-2-aminovinyl)quinoxaline-2-carbonitriles. Their base-induced cyclization gave the previously unknown pyrido[3,4-b]quinoxalin-1(2H)-imines or pyrido[3,4-b]quinoxalin-1-amines. 3-Alkynylquinoxaline-2-carbonitriles were directly transformed into pyrido[3,4-b]quinoxalin-1(2H)-imines by heating with an alkylamine and K2CO3 in DMF. The ionization constants, and absorption and fluorescent properties of the resulted pyrido[3,4-b] quinoxalin-1(2H)-imines were measured. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.005
• 作为产物：
  描述：

  2-氯喹喔啉-3-甲腈 、 苯乙炔 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 2.33h， 以92%的产率得到3-(phenylethynyl)quinoxaline-2-carbonitrile
  参考文献：
  名称：

  Nucleophilic cyclization of 3-alkynylquinoxaline-2-carbonitriles into pyrido[3,4-b]quinoxalines

  摘要：

  3-Alkynylquinoxaline-2-carbonitriles have been synthesized from 3-chloroquinoxaline-2-carbonitrile via the Sonogashira reaction. Treatment of 3-alkynylquinoxaline-2-carbonitriles with an alkylamine or ammonia has been shown to produce stable enamines, e.g., (Z)-3-(2-aryl-2-aminovinyl)quinoxaline-2-carbonitriles. Their base-induced cyclization gave the previously unknown pyrido[3,4-b]quinoxalin-1(2H)-imines or pyrido[3,4-b]quinoxalin-1-amines. 3-Alkynylquinoxaline-2-carbonitriles were directly transformed into pyrido[3,4-b]quinoxalin-1(2H)-imines by heating with an alkylamine and K2CO3 in DMF. The ionization constants, and absorption and fluorescent properties of the resulted pyrido[3,4-b] quinoxalin-1(2H)-imines were measured. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.09.005

文献信息

• 1,3-Dipolar cycloaddition of azinium ylides to alkynyl hetarenes: a synthetic route to indolizine and pyrrolo[2,1-a]isoquinoline based heterobiaryls
  作者：Julia I. Nelina-Nemtseva、Anna V. Gulevskaya、Alexander F. Pozharskii、Huong T.L. Nguyen、Ekaterina A. Filatova

  DOI：10.1016/j.tet.2016.03.050

  日期：2016.5

  For the first time, π-deficient alkynyl hetarenes were used as dipolarophiles in a 1,3-dipolar cycloaddition reaction with in situ generated azinium ylides. A three-component reaction of pyridine or isoquinoline, ethyl chloroacetate and alkynyl hetarene (pyrazine, quinoxaline, uracil, or lumazine derivative) in the presence of a base gave the corresponding indolizine or pyrrolo[2,1-a]isoquinoline based

  第一次，在与原位生成的叠氮化物的1，3-偶极环加成反应中，将π缺乏的炔基戊烯用作亲极性。在碱存在下，吡啶或异喹啉，氯乙酸乙酯和炔基戊烯（吡嗪，喹喔啉，尿嘧啶或lumazine衍生物）的三组分反应得到相应的吲哚利嗪或吡咯并[2,1- a ]异喹啉基杂联芳基产量。反应以高区域选择性进行；在所有情况下，C中最缺乏电子的碳原子起始炔基戊烯的C键加到叠氮基内鎓盐的侧链碳上。炔基戊烯与叠氮化或其他1,3-偶极试剂的1,3-偶极环加成反应可以被视为杂联芳基的另一种合成方法。
• Base-promoted cyclization of 3-alkynylquinoxaline-2-carbonitriles with CH-acids: a new method for the phenazine ring synthesis
  作者：Huong T.L. Nguyen、Anna V. Gulevskaya、Alexander F. Pozharskii、Julia I. Nelina-Nemtseva

  DOI：10.1016/j.tet.2014.05.023

  日期：2014.8

  THF or DMSO. A new cascade process includes nucleophilic addition of a CH-acid carbanion to the CC bond of 3-alkynylquinoxaline-2-carbonitrile, 6-exo-dig cyclization of the intermediate allyl carbanion with the formation of 2,2-disubstituted 1-imino-1,2-dihydrophenazine and its aromatization via elimination of the C(2)-substituent. Several secondary reactions were also disclosed and discussed.

  3- Alkynylquinoxaline -2-腈直接通过用CH-酸（丙二酸二乙酯，氰基乙酸乙酯，丙二腈，2- tosylacetonitrile，2-（1-甲基-1-处理转化为2,3-二取代的吩嗪-1-胺ħ -在THF或DMSO中的苯并[ d ]咪唑-2-基）乙腈，硝基甲烷）和t- BuOK。一种新的级联工艺包括将CH-酸碳负离子亲核加成到3-炔基喹喔啉-2-甲腈的C C键上，中间烯丙基碳负离子的6- exo - dig环化反应，形成2,2-二取代的1-亚氨基-1,2-二氢吩嗪及其通过消除C（2）取代基的芳香化作用。还公开和讨论了一些次级反应。
• Nucleophilic cyclization of 3-alkynylquinoxaline-2-carbonitriles into pyrido[3,4-b]quinoxalines
  作者：Alexander S. Tyaglivy、Anna V. Gulevskaya、Alexander F. Pozharskii、Olga I. Askalepova

  DOI：10.1016/j.tet.2013.09.005

  日期：2013.11

  3-Alkynylquinoxaline-2-carbonitriles have been synthesized from 3-chloroquinoxaline-2-carbonitrile via the Sonogashira reaction. Treatment of 3-alkynylquinoxaline-2-carbonitriles with an alkylamine or ammonia has been shown to produce stable enamines, e.g., (Z)-3-(2-aryl-2-aminovinyl)quinoxaline-2-carbonitriles. Their base-induced cyclization gave the previously unknown pyrido[3,4-b]quinoxalin-1(2H)-imines or pyrido[3,4-b]quinoxalin-1-amines. 3-Alkynylquinoxaline-2-carbonitriles were directly transformed into pyrido[3,4-b]quinoxalin-1(2H)-imines by heating with an alkylamine and K2CO3 in DMF. The ionization constants, and absorption and fluorescent properties of the resulted pyrido[3,4-b] quinoxalin-1(2H)-imines were measured. (C) 2013 Elsevier Ltd. All rights reserved.