6-Chloro-2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridine-3-carbaldehyde

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 6-Chloro-2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridine-3-carbaldehyde
• 英文别名: 6-Chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde
• 化学式: C₁₅H₁₁ClN₂O₂
• 分子量: 286.718
• InChiKey: VTDLZXONARXJRL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  43.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  6-Chloro-2-(4-methoxy-phenyl)-imidazo[1,2-a]pyridine-3-carbaldehyde 在 manganese(IV) oxide 、 溶剂黄146 、 三乙胺 作用下， 以 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-4-[6-chloro-2-(4-methoxyphenyl)imidazo[1,2-a]pyridine-3-yl]-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile
  参考文献：
  名称：

  One-Step Synthesis of Heterocyclic Privileged Medicinal Scaffolds by a Multicomponent Reaction of Malononitrile with Aldehydes and Thiols

  摘要：

  Heterocyclic privileged medicinal scaffolds involving pyridine, 1,4-dihydropyridine, chromeno[2,3-b]pyridine, and dihydro-1,4-dithiepine frameworks are prepared via a single-step multicomponent reaction of structurally diverse aldehydes with various thiols and malononitrile. Mechanistic studies of the synthetic pathway leading to pyridines reveal that 1,4-dihydropyridines undergo oxidation by the intermediate Knoevenagel adducts rather than by air oxygen. The use of o,o'-disubstituted aromatic aldehydes leads to the corresponding 1,4-dihydropyridines, whereas salicylic aldehydes result in chromeno[2,3-b]pyridines. Reactions of ethanedithiol as a thiol component produce dimeric pyridines with sterically unencumbered aldehydes, while o,o'-disubstituted aromatic aldehydes give dihydro-1,4-dithiepines. Thus, depending on the aldehyde and thiol types, diverse libraries of medicinally relevant compounds can be prepared by a simple one-step process involving no chromatography.

  DOI：

  10.1021/jo070114u

文献信息

• Ru(II)-Catalyzed Synthesis of Fused Imidazo[1,2-<i>a</i>]pyridine-chromenones and Methylene-Tethered Bis-imidazo[1,2-<i>a</i>]pyridines and Regioselective O-Acetoxylation of Imidazo[1,2-<i>a</i>]pyridines
  作者：Javeed Ahmad Tali、Ravi Shankar

  DOI：10.1021/acs.orglett.3c00578

  日期：2023.5.12

  unprecedented protocol via ruthenium-catalyzed annulation for the synthesis of 6H-chromeno[4′,3′:4,5]imidazo[1,2-a]pyridin-6-one, and functionalized 2-(3-formylimidazo[1,2-a]pyridin-2-yl)phenyl acetate has been revealed by intramolecular chelation-assisted C–H activation. Additionally, a one-pot approach for creating bis(2-phenylimidazo[1,2-a]pyridin-3-yl)methane (BIP) has been realized through ruthenium

  在此，我们公开了一种前所未有的通过钌催化环化合成 6 H -chromeno[4',3':4,5]imidazo[1,2- a ]pyridin-6-one 和功能化 2-(已通过分子内螯合辅助的 C-H 活化揭示了3-甲酰咪唑并 [1,2- a ] 吡啶-2-基) 乙酸苯酯。此外，通过使用甲酸的钌催化，已经实现了用于产生双（2-苯基咪唑并[1,2- a ]吡啶-3-基）甲烷（BIP）的一锅法。该方法用于 BIP 的克级合成和已上市药物佐利米丁的经济步骤后期功能化，收率良好。
• Bi-functional complexes and methods for making and using such complexes
  申请人：Gouliaev Alex Haahr

  公开号：US11225655B2

  公开（公告）日：2022-01-18

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.

  本发明涉及一种合成双功能复合物的方法，该复合物包括分子部分和识别分子部分的识别寡核苷酸部分。根据本发明的合成方法的一部分优选在一种或多种有机溶剂中进行，此时包含可选保护标签或寡核苷酸标识符的新生双功能复合物与固体支持物相连接，合成方法的另一部分优选在适合于将寡核苷酸标签酶加到溶液中的新生双功能复合物的条件下进行。
• One-Step, Three-Component Synthesis of Pyridines and 1,4-Dihydropyridines with Manifold Medicinal Utility
  作者：Nikolai M. Evdokimov、Igor V. Magedov、Artem S. Kireev、Alexander Kornienko

  DOI：10.1021/ol052994+

  日期：2006.3.2

  Privileged medicinal scaffolds based on the structures of 2-amino-3,5-dicyano-6-sulfanylpyridines and the corresponding 1,4-dihydropyridines have been prepared via a single-step, three-component reaction of structurally diverse aldehydes with various thiols and malononitrile. Mechanistic studies revealed that 1,4-dyhidropyridines undergo oxidation by the intermediate Knoevenagel adducts rather than by air oxygen. Although the latter process undermines the yields of pyridines, it results in the formation of substituted enaminonitriles, promising antiinflammatory agents.
• BI-FUNCTIONAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Nuevolution A/S

  公开号：EP2558577B1

  公开（公告）日：2018-12-12
• BI-FUNCTINAL COMPLEXES AND METHODS FOR MAKING AND USING SUCH COMPLEXES
  申请人：Gouliaev Alex Haahr

  公开号：US20130281324A1

  公开（公告）日：2013-10-24

  The present invention is directed to a method for the synthesis of a bi-functional complex comprising a molecule part and an identifier oligonucleotide part identifying the molecule part. A part of the synthesis method according to the present invention is preferably conducted in one or more organic solvents when a nascent bi-functional complex comprising an optionally protected tag or oligonucleotide identifier is linked to a solid support, and another part of the synthesis method is preferably conducted under conditions suitable for enzymatic addition of an oligonucleotide tag to a nascent bi-functional complex in solution.