2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡啶及其衍生物
• 英文名称: 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile
• 英文别名: 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-3,5-dicyano-4-phenyl-6-ethoxypyridine；2-[(4-Chlorodithiazol-5-ylidene)amino]-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile；2-[(4-chlorodithiazol-5-ylidene)amino]-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile
• 化学式: C₁₇H₁₀ClN₅OS₂
• 分子量: 399.884
• InChiKey: VNCWOYFDVBVWGB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  145
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile 以 二氯甲烷 为溶剂， 反应 5.17h， 生成 2-(dipyrrolidin-1-ylmethyleneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile
  参考文献：
  名称：

  Transformation of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile into 4-aminopyrido[2,3-d]pyrimidines and 2-(pyrid-2-yl)guanidines

  摘要：

  The reactions of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylPyridine-3,5-dicarbonitrile (14) with a range of primary and secondary amines are investigated. Treatment with n-BuNH2 and BnNH2 gave 1,3-di-n-butyl- and 1,3-dibenzy1-2-(3,5-dicyano-6-ethoxy-4-phenylpyrid-2-yl) guanidines 15a (32%) and 15b (82%), respectively. While treatment with Et2NH, n-Pr2NH or Bn2NH gave the analogous 4-dialkylaminopyrido[2,3-d]pyrimidines 16c-e in high yields. Treatment of the dithiazole 14 with pyrrolidine, piperidine or morpholine gave the analogous 4-dialkylaminopyrido[2,3-d]pyrimidines 16f-h, the 2-aminopyridine 13 and 2-(diamino-1-ylmethyleneamino)-6-ethoxy-4-phenylpyridine3,5-dicarbonitriles 15f-h. The 4-diallcylaminopyrido[2,3-d]pyrimidines 16f-h are converted to the 2(dialkylamino-1-ylmethyleneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitriles 15f-h upon further reaction with excess dialkylamines. The structure and origins of the two side products 17 and 18 are also discussed. Tentative mechanisms for these transformations are proposed. (C) 2015 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2015.02.006

文献信息

• Synthesis of 5,5′-Diarylimino Quinoidal 2,2′-Bithiazoles
  作者：Maria Koyioni、Panayiotis A. Koutentis

  DOI：10.1021/acs.orglett.6b03474

  日期：2017.1.6

  (het)arylamines and subsequent in situ Ag2O-mediated oxidation provides access to cross-conjugated quinoidal 5,5′-diarylimino-2,2′-bithiazoles in moderate to high yield. The highly colored quinoidal 2,2′-bithiazoles were studied by UV/vis spectroscopy, cyclic voltammetry and computational methods.

  Pd（0）催化5,5'-二溴-2,2'-噻唑与（het）芳胺的双C–N偶联反应以及随后的原位Ag 2 O介导的氧化作用提供了交叉共轭醌5 5'-diarylimino-2,2'-bithiazoles，中等至高收率。通过紫外/可见光谱，循环伏安法和计算方法研究了高度着色的醌型2,2'-联噻唑。
• Transformation of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitrile into 4-aminopyrido[2,3-d]pyrimidines and 2-(pyrid-2-yl)guanidines
  作者：Andreas S. Kalogirou、Sophia S. Michaelidou、Andrew J.P. White、Panayiotis A. Koutentis

  DOI：10.1016/j.tet.2015.02.006

  日期：2015.3

  The reactions of 2-(4-chloro-5H-1,2,3-dithiazol-5-ylideneamino)-6-ethoxy-4-phenylPyridine-3,5-dicarbonitrile (14) with a range of primary and secondary amines are investigated. Treatment with n-BuNH2 and BnNH2 gave 1,3-di-n-butyl- and 1,3-dibenzy1-2-(3,5-dicyano-6-ethoxy-4-phenylpyrid-2-yl) guanidines 15a (32%) and 15b (82%), respectively. While treatment with Et2NH, n-Pr2NH or Bn2NH gave the analogous 4-dialkylaminopyrido[2,3-d]pyrimidines 16c-e in high yields. Treatment of the dithiazole 14 with pyrrolidine, piperidine or morpholine gave the analogous 4-dialkylaminopyrido[2,3-d]pyrimidines 16f-h, the 2-aminopyridine 13 and 2-(diamino-1-ylmethyleneamino)-6-ethoxy-4-phenylpyridine3,5-dicarbonitriles 15f-h. The 4-diallcylaminopyrido[2,3-d]pyrimidines 16f-h are converted to the 2(dialkylamino-1-ylmethyleneamino)-6-ethoxy-4-phenylpyridine-3,5-dicarbonitriles 15f-h upon further reaction with excess dialkylamines. The structure and origins of the two side products 17 and 18 are also discussed. Tentative mechanisms for these transformations are proposed. (C) 2015 Elsevier Ltd. All rights reserved.