N-(tert-butyl)-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine | 334002-17-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: N-(tert-butyl)-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
• 英文别名: tert-Butyl-(2-thiophen-2-yl-imidazo[1,2-a]pyridin-3-yl)-amine；N-tert-butyl-2-thiophen-2-ylimidazo[1,2-a]pyridin-3-amine
• CAS: 334002-17-4
• 化学式: C₁₅H₁₇N₃S
• 分子量: 271.386
• InChiKey: ORDKAKDRMJQWGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  57.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  N-(tert-butyl)-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine 在 碘苯二乙酸 、 对甲苯磺酸 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 1.0h， 以81%的产率得到N-(tert-Butyl)-2-oxo-2-(thiophen-2-yl)acetamide
  参考文献：
  名称：

  Diverse Oxidative C(sp²)–N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides

  摘要：

  An efficient and chemoselective C(sp(2))-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as alpha-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some alpha-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.

  DOI：

  10.1021/acs.joc.9b00208
• 作为产物：
  描述：

  N-tert-butyl-2-(3-nitrophenyl)imidazo[1,2-a]pyridin-3-amine 在 碘苯二乙酸 、 对甲苯磺酸 作用下， 以 乙醇 、 1,2-二氯乙烷 为溶剂， 反应 2.0h， 生成 N-(tert-butyl)-2-(thiophen-2-yl)imidazo[1,2-a]pyridin-3-amine
  参考文献：
  名称：

  Diverse Oxidative C(sp²)–N Bond Cleavages of Aromatic Fused Imidazoles for Synthesis of α-Ketoamides and N-(pyridin-2-yl)arylamides

  摘要：

  An efficient and chemoselective C(sp(2))-N bond cleavage of aromatic imidazo[1,2-a]pyridine molecules is developed. A broad scope of amide compounds such as alpha-ketoamides and N-(pyridin-2-yl)arylamides are afforded as the final products in up to quantitative yields. Diverse C-N bond cleavages are controlled by the oxidative species used in this transformation, with various amide products afforded in a chemoselective fashion. A preliminary study indicated that some alpha-ketoamides exhibit anti-Tobacco Mosaic Virus activity for potential use in plant protection.

  DOI：

  10.1021/acs.joc.9b00208

文献信息

• An Efficient, Regioselective, Versatile Synthesis of N-Fused 2- and 3-Aminoimidazoles via Ugi-Type Multicomponent Reaction Mediated by Zirconium(IV) Chloride in Polyethylene Glycol-400
  作者：Sankar Guchhait、Chetna Madaan

  DOI：10.1055/s-0028-1087915

  日期：2009.3

  An Ugi-type multicomponent reaction of heterocyclic amidines with aldehydes and isocyanides catalyzed by zirconium(IV) chloride in PEG-400 was developed. The protocol offers the rapid, environment friendly, regioselective and versatile synthesis of medicinally important N-fused 2- and 3-aminoimidazoles in good to high yields. The combination of catalyst and solvent, that was judiciously explored, was

  开发了 PEG-400 中氯化锆 (IV) 催化的杂环脒与醛和异氰化物的 Ugi 型多组分反应。该协议提供了快速、环境友好、区域选择性和多功能的医学上重要的 N-融合 2-和 3-氨基咪唑的合成，产量高。明智地探索了催化剂和溶剂的组合，对于该方法的区域选择性和多功能性至关重要。
• Bicyclic imidazo-3-yl-amine derivatives
  申请人：GRUENENTHAL GMBH

  公开号：US20030018032A1

  公开（公告）日：2003-01-23

  Substituted bicyclic imidazo-3-yl-amines and medicaments comprising these compounds, useful, inter alia, as analgesics.

  取代的双环咪唑-3-基胺及含有这些化合物的药物，可用作镇痛剂等。
• 二環状イミダゾ−３−イル−アミン誘導体
  申请人：グリュネンタール・ゲゼルシャフト・ミト・ベシュレンクテル・ハフツング

  公开号：JP2003511451A

  公开（公告）日：2003-03-25

  \n (57)【要約】\n本発明は、その塩基又は薬学的に許容し得る塩の形での一般式Ｉで表わされる二環状イミダゾ−３−イル−アミン類、その製造方法及び有効物質として、請求項１記載の少なくとも１種の一般式Ｉで表わされる二環状イミダゾ−３−イル−アミンをその塩基又は薬学的に許容し得る塩の形で含有する医薬に関する。\n

  \(57)/n (57)/n (57)/n (57)/n (57)/n (57)/n (57)/n (57)/n (57)/n (57)/n (57)/n (57)/n (57)} 本发明涉及通式 I 所代表的双环咪唑-3-基-胺，其形式为它们的碱或药学上可接受的盐，它们的生产方法和至少一种作为活性物质的药物，如权利要求 1 所述。关于含有通式Ⅰ所代表的双环咪唑-3-基-胺以其碱或药学上可接受的盐形式存在的药物。\n
• A Facile Preparation of Imidazo[1,2-a]pyridin-3-amine Derivatives via a Three-Component Reaction with β-Cyclodextrin–SO3H as Catalyst
  作者：Jian Wu、Fang-Zhou Xu、She-Lei Feng、Wei Xue、Zhen-Zhen Wang

  DOI：10.3987/com-16-13508

  日期：——

  Because heterogeneous catalysts have attracted great interest in organic chemistry, this paper reports facile beta-cyclodextrin-SO3H catalyzed cyclization to form imidazo[1,2-a]pyridin-3-amine derivatives via a three-component reaction. The main advantages of this strategy include short reaction time, practical simplicity, and high yield, and the catalyst can be separated easily by filtration and reused at least four times.
• BICYCLISCHE IMIDAZO-3-YL-AMINDERIVATE
  申请人：Grünenthal GmbH

  公开号：EP1218382A2

  公开（公告）日：2002-07-03