3-氨基-2(1H)-喹喔啉硫酮 | 34972-19-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 中文名称: 3-氨基-2(1H)-喹喔啉硫酮
• 英文名称: 3-aminoquinoxaline-2-thione
• 英文别名: 3-Aminochinoxalin-2-thion；3-amino-1H-quinoxaline-2-thione；2-Aminoquinoxaline-3-thiol；3-amino-1H-quinoxaline-2-thione
• CAS: 34972-19-5
• 化学式: C₈H₇N₃S
• mdl: MFCD18448653
• 分子量: 177.23
• InChiKey: BKMAKIRBBBDROA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  82.5
• 氢给体数：
  2
• 氢受体数：
  2

安全信息

• 海关编码：
  2933990090

反应信息

• 作为反应物：
  描述：

  3-氨基-2(1H)-喹喔啉硫酮 在 二氯化硫 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以66%的产率得到C₈H₃Cl₄N₃S₂
  参考文献：
  名称：

  Quinoxaline-1,2,3-dithiazolyls — Synthesis, EPR characterization, and redox chemistry

  摘要：

  Oxidation of quinoxalineaminothiol with SCl2 or S2Cl2/Cl-2 affords a series of compounds based on the quinoxaline-1,2,3-dithiazole framework QDTA. Under highly oxidizing conditions, the 1,2,3-dithiazolyl ring is opened to afford the acyclic dichlorosulfimino-sulfenyl chlorides Cl-x-QDTA-Cl-3 (x = 0, 1, 2). Reduction of these "trichloro" compounds leads to ring closure. For x = 2, reduction using S2Cl2 affords the dithiazolylium chloride [Cl-2-QDTA][Cl]. For all values of x, reduction with iodide ion (3 mol equiv) affords the corresponding dithiazolyl radical [Cl-x-QDTA]. The radicals can be isolated in good yield in crude form, but attempts to purify them by vacuum sublimation lead to thermal degradation. The radicals have nonetheless been fully characterized by EPR spectroscopy, and the assignments of the observed hyperfine coupling constants cross-matched with those obtained by computation at the B3LYP/6-31G** level. The structures of the trichloro compounds Cl-x-QDTA-Cl-3 (x = 1, 2) have been confirmed by X-ray crystallography. Crystal data: Cl-QDTA-Cl-3, monoclinic, space group C2/c, a = 30.561(5) Angstrom, b = 4.9764(9) Angstrom, c = 22.247(4) Angstrom, beta = 131.822(14)degrees, V = 2521.4(8) Angstrom (3), Z = 8, R(F) = 0.043, and R-w(F) [I greater than or equal to sigma (I)] = 0.049; Cl-2-QDTA-Cl-3, orthorhombic, space group Pnma, a = 18.627(12) Angstrom, b = 6.848(4) Angstrom, c = 10.926(7) Angstrom, V = 1393.7(15) Angstrom (3), Z = 4, R(F) = 0.047, and R-w(F) [I greater than or equal to 3 sigma (I)] = 0.060.

  DOI：

  10.1139/cjc-79-9-1352
• 作为产物：
  描述：

  2,3-喹噁啉二硫醇 在 氨 作用下， 反应 3.0h， 生成 3-氨基-2(1H)-喹喔啉硫酮
  参考文献：
  名称：

  新型二苯胺基荧光苯乙烯基着色剂的合成及其热，光物理和电化学性质的研究

  摘要：

  摘要以4,4'-（己基氨基）双（苯甲醛）为供体和2-甲基噻唑并[4,5- b ]喹喔啉衍生物合成了三种新颖的“ Y”形受体-π-供体-π-受体型化合物。作为通过经典的Knoevenagel缩合而冷凝的强电子受体。研究了它们的吸收，发射，热性能和电化学稳定性。发现这些化合物的强电子受体-供体发色体系表现出高的斯托克斯位移，出色的热稳定性和电化学可逆性。通过使用各种溶剂（例如甲苯，氯仿，乙酸乙酯，四氢呋喃，甲醇和N，N）研究了这些着色剂的溶剂化行为。-二甲基甲酰胺按极性增加的顺序排列。通过元素分析，1 H NMR和质谱对染料进行表征。 图形概要

  DOI：

  10.1007/s00706-010-0365-6

文献信息

• Synthesis of 2-substituted-4-methyl-5,13-dihydropyrimido[4′,5′:5,6][1,4]thiazepino[2,3-<i>b</i>]quinoxaline as a new heterocyclic system
  作者：Marzieh Akbarzadeh、Mehdi Bakavoli、Hossein Eshghi、Ali Shiri、Hamid Azizollahi、Joel T. Mague

  DOI：10.1080/10426507.2018.1455199

  日期：2018.9.2

  GRAPHICAL ABSTRACT ABSTRACT 2-Substituted-4-methyl-5,13-dihydropyrimido[4′,5′:5,6][1,4]thiazepino[2,3-b]quinoxalines (7a-g), derivatives of a new heterocyclic system were synthesized through cyclocondensation of 2,4-dichloro-5-(chloromethyl)-6-methylpyrimidine (3) with 3-aminoquinoxaline-2-thiol (4) and subsequent substitution by various secondary amines. Regioselective heterocyclization was confirmed

  图形摘要 摘要 2-Substituted-4-methyl-5,13-dihydropyrimido[4',5':5,6][1,4]thiazepino[2,3-b]quinoxalines (7a-g)，a 的衍生物通过 2,4-二氯-5-(氯甲基)-6-甲基嘧啶 (3) 与 3-氨基喹喔啉-2-硫醇 (4) 的环缩合反应，并随后被各种仲胺取代，合成了新的杂环体系。4-methyl-2-(pyrrolidin-1-yl)-5,13-dihydropyrimido[4',5':5,6] [1,4]thiazepino[2, 3-b]喹喔啉 (7a)。
• A Novel Ionic Liquid Based on Imidazolium Cation as an Efficient and Reusable Catalyst for the One-pot Synthesis of Benzoxazoles, Benzthiazoles, Benzimidazoles and 2-Arylsubstituted Benzimidazoles
  作者：Maede Hasanpour、Hossein Eshghi、Mehdi Bakavoli、Mahdi Mirzaeia

  DOI：10.1002/jccs.201400372

  日期：2015.5

  A novel dicationic ionic liquid based on imidazolium cation is designed, synthesized and successfully used as catalyst for the one‐pot synthesis of benzoxazoles, benzthiazoles, benzimidazoles and 2‐arylsubstituted benzimidazoles. The remarkable feature of this new catalyst is its ethyleneoxy bridge which participates in dissolving organic compound in ionic liquid. The application of this ionic liquid

  设计，合成了一种基于咪唑阳离子的新型离子型离子液体，并成功用作一锅合成苯并恶唑，苯并噻唑，苯并咪唑和2-芳基取代的苯并咪唑的催化剂。这种新催化剂的显着特点是它的亚乙基氧基桥参与了将有机化合物溶解在离子液体中。在一种新的单锅法中研究了这种离子液体的应用，该方法可在无溶剂条件下合成杂环化合物。该方法的优点是操作简便，转化率高，催化剂的可重复使用性，纯化简便，反应时间短。
• Purine analogues as amplifiers of phleomycin. IX. Some 2- and 6-substituted Thiazolo[4,5-b]pyrazines, 2-substituted Thiazolo[4,5-c]- and Thiazolo[5,4-b]-pyridines and related compounds
  作者：GB Barlin、SJ Ireland、BJ Rowland

  DOI：10.1071/ch9841729

  日期：——

  Derivatives of the thiazolo[4,5-b]pyrazine system are reported including those with 2-phenyl substituents or fused benzene rings (as in thiazolo[4,5-b]quinoxalines) together with strongly basic N,N-dimethylaminoethylthio or N,N-dimethylaminopropylthio side chains. Series of thiazolo[4,5-c]- pyridines, thiazolo[5,4-b]pyridines and quinoxalines are also described. A new process for the preparation of 3-N,N-dimethylaminopropylthio derivatives of heterocycles by reaction of the mercapto compound with 3-chloro-N,N-dimethylpropylamine in ethanolic ammonia has been shown to give more reliable and improved results. Of the compounds examined for amplification of the activity of phleomycin, N,N-dimethyl- 3-(2-methylthiazolo[4,5-pyrazin-6-ylthio)propylamine and 3-[3-(3-N,N-dimethylaminopropylthio)- quinoxalin-2-ylthiol-N,N-dimethylpropylamine were the best, and showed four star activity at 1 mM and 0.5 mM respectively. A 2-phenyl substituent in, or a benzene ring fused to, thiazolo[4,5-b]- pyrazines did not increase amplification. The 2-substituted thiazolo[4,5-c]pyridines showed activity comparable to that of the 2-substituted thiazolo[4,5-blpyrazines whereas that of the thiazolo[5,4-b]pyrazines was lower.

  据报道，噻唑并[4,5-b]吡嗪系统的衍生物包括以下几种 (如噻唑并[4,5-b]喹喔啉)以及强碱性 N,N-二甲氨基乙硫基或 N,N-二甲氨基丙硫基侧链。 侧链。此外，还介绍了噻唑并[4,5-c]吡啶、噻唑并[5,4-b]吡啶和喹喔啉系列。 系列。制备 3-N,N-二甲氨基丙硫基杂环衍生物的新工艺 巯基化合物与 3-氯-N,N-二甲基丙胺在乙醇氨中的反应 在乙醇氨中的反应，结果更可靠、更有效。 在研究过的能增强新霉素活性的化合物中，N,N-二甲基- 3-(2-甲基噻吩) 3-(2-甲基噻唑并[4,5-吡嗪-6-基硫基)丙胺 和 3-[3-(3-N,N-二甲基氨基丙硫基)-喹喔啉-2-基硫基]的活性。 喹喔啉-2-硫醇-N,N-二甲基丙胺的活性最好，在 1 mM 和 0 mM 浓度下显示出四星级活性。 星级活性，浓度分别为 1 毫摩尔和 0.5 毫摩尔。 分别显示出四星级活性。噻唑并[4,5-b]-吡嗪中的 2-苯基取代基或苯环与噻唑并[4,5-b]-吡嗪融合并不能提高扩增率。 并不增加扩增。2 取代的噻唑并[4,5-c]吡啶 的活性与 2-取代的噻唑并[4,5-b]吡嗪的活性相当。 而噻唑并[5,4-b]吡嗪的活性较低。
• One-pot, Procedure for the Preparation of some Thiazino[2,3-b]quinoxaline Derivatives
  作者：Mehdi Bakavoli、Hossein Eshghi、Hamid Azizollahi、Sattar Saberi、Faezeh Bazrafshan

  DOI：10.3184/174751914x13926569127947

  日期：2014.3

  and convenient synthesis of new thiazino[2,3-b]quinoxaline derivatives has been developed by employing a one-pot cyclo-condensation of several α-haloketones and 3-aminoquinoxaline-2-thiol in acetic acid. A similar reaction with 4-bromo-3-methyl-4,5-dihydro-1H-5-pyrazolone gave a new heterocyclic system, 3-methyl-1,4-dihydropyrazolo[4′,3′:5,6][1,4] thiazino[2,3-b]quinoxaline.

  通过使用几种 α-卤代酮和 3-氨基喹喔啉-2-硫醇在乙酸中的一锅环缩合反应，开发了一种高效、方便的新型噻嗪并 [2,3-b] 喹喔啉衍生物的合成方法。与 4-bromo-3-methyl-4,5-dihydro-1H-5-pyrazolone 的类似反应得到了一个新的杂环体系，3-methyl-1,4-dihydropyrazolo[4',3':5,6][ 1,4]噻嗪并[2,3-b]喹喔啉。
• Site Selectivity in Reactions of Hydrazonoyl Halides With 2-Amino-3-quinoxalinethiol: A New General Access to Functionalized 4H-1,3,4-Thiadiazino-[5,6-b]quinoxalines
  作者：Ahmad Sami Shawali、M. A. N. Mosselhi、Thoraya A. Farghaly

  DOI：10.1080/104265090921100

  日期：2005.10

  The synthesis of various 2,4-disubstituted 4H-1,3,4-thiadiazino-[5,6-b]quinoxalines via reaction of hydrazonoyl halides with 2-amino-3-quinoxalinethiol in ethanol in the presence of sodium ethoxide is described. The structures of the reaction products were elucidated by chemical evidence and by their IR, 1 H, 13 C-NMR, and MS spectra. The mechanism of the formation of the products is also discussed

  描述了在乙醇钠存在下，通过腙酰卤与 2-氨基-3-喹喔啉硫醇在乙醇中的反应合成各种 2,4-二取代的 4H-1,3,4-噻二嗪基-[5,6-b] 喹喔啉. 反应产物的结构通过化学证据和它们的 IR、 1 H、 13 C-NMR 和 MS 光谱阐明。还讨论了产物的形成机制。