7-methyl-2-(thiophen-2-yl)imidazo[1,2-a]pyridine | 364043-74-3

• 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: 7-methyl-2-(thiophen-2-yl)imidazo[1,2-a]pyridine
• 英文别名: 7-methyl-2-thiophen-2-ylimidazo[1,2-a]pyridine
• CAS: 364043-74-3
• 化学式: C₁₂H₁₀N₂S
• mdl: MFCD23713819
• 分子量: 214.291
• InChiKey: IHOXXWZJYDBYTP-UHFFFAOYSA-N

物化性质

• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  15
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.083
• 拓扑面积：
  45.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  7-methyl-2-(thiophen-2-yl)imidazo[1,2-a]pyridine 在 sodium acetate 作用下， 以 水 、 溶剂黄146 为溶剂， 反应 5.0h， 生成 7-Methyl-3-(phenethylsulfanylmethyl)-2-(2-thienyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Influence of 2-Substituent on the Activity of Imidazo[1,2-a] Pyridine Derivatives Against Human Cytomegalovirus

  摘要：

  The synthesis of various 2-substituted imidazo[1,2-a]pyridine bearing a thioether side chain in position 3 was reported. The new compounds were characterized by H-1 and C-13 NMR spectra. A conformational study was obtained by X-ray crystallographic analysis for 2-biphen-4-ylimidazopyridine 7. The antiviral activity against human cytomegalovirus (HCMV) was investigated. It was strongly influenced by the nature of C-2 substituent. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00347-9
• 作为产物：
  描述：

  2-乙酰基噻吩 在 盐酸羟胺 、 sodium acetate 、 copper dichloride 作用下， 以 乙醇 、 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 反应 24.0h， 生成 7-methyl-2-(thiophen-2-yl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  肟酯的CuCl 2催化的N O键裂解：咪唑杂环和呋喃[3,2- c ]苯并稠合的咪唑的方法

  摘要：

  通过用几种肟酯与一组2-氨基氮杂氮杂铜进行铜催化的氮杂环化反应，开发了一种以良好至高收率的多种咪唑杂环杂环的铰接方法。上述环化反应可能是通过单电子转移过程进行的，这体现了一种新技术，该技术为咪唑环合成生成两个新的C N键。令人欣慰的是，该化学方法的实施可以进一步扩展为通过连续的C N键形成，合成带有呋喃[3,2- c ]亚甲基部分的新型稠合咪唑，随后是C（sp 2）-H功能化/ 5-内切-乙氧基环化（CC和C在铜（II）作为π亲电Lewis酸催化剂的情况下，原位生成带有环状烯酮的稠合咪唑。

  DOI：

  10.1016/j.tetlet.2020.152147

文献信息

• Iodine-catalyzed regioselective thiolation of imidazo[1,2-a]pyridines using sulfonyl hydrazides as a thiol surrogate
  作者：Avik Kumar Bagdi、Shubhanjan Mitra、Monoranjan Ghosh、Alakananda Hajra

  DOI：10.1039/c5ob00033e

  日期：——

  sulfenylation of imidazo[1,2-a]pyridines via C(sp(2))-H bond functionalization has been achieved using sulfonyl hydrazides as a thiol surrogate. A library of 3-sulfanylimidazopyridines with broad functionalities was synthesized under metal and oxidant-free practical reaction conditions. This methodology is also applicable for the regioselective sulfenylation of imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole

  碘催化的咪唑并[1,2-a]吡啶类通过C（sp（2））-H键功能化的区域选择性亚磺酰基已经使用磺酰肼作为硫醇替代物实现了。在没有金属和氧化剂的实际反应条件下，合成了具有广泛功能的3-磺酰胺基咪唑并吡啶类化合物的文库。该方法也适用于咪唑并[2,1-b]噻唑和苯并[d]咪唑并[2,1-b]噻唑的区域选择性亚磺酰基化。
• Regioselective Oxidative Trifluoromethylation of Imidazoheterocycles via C(sp²)–H Bond Functionalization
  作者：Kamarul Monir、Avik Kumar Bagdi、Monoranjan Ghosh、Alakananda Hajra

  DOI：10.1021/jo502928e

  日期：2015.2.6

  been carried out at room temperature through the functionalization of the sp2 C–H bond employing Langlois reagent under ambient air. A library of 3-(trifluoromethyl)imidazo[1,2-a]pyridines with broad functionalities have been synthesized regioselectively. This methodology is also applicable to imidazo[2,1-b]thiazole and benzo[d]imidazo[2,1-b]thiazole.

  咪唑并吡啶的氧化三氟甲基化反应已在室温下通过使用Langlois试剂对sp 2 C–H键进行官能化来进行。已经选择性地合成了具有广泛功能的3-（三氟甲基）咪唑并[1,2- a ]吡啶的文库。该方法也适用于咪唑并[2,1- b ]噻唑和苯并[ d ]咪唑并[2,1- b ]噻唑。
• Copper-Catalyzed Synthesis of Imidazo[1,2-<i>a</i>]pyridines through Tandem Imine Formation-Oxidative Cyclization under Ambient Air: One-Step Synthesis of Zolimidine on a Gram-Scale
  作者：Avik Kumar Bagdi、Matiur Rahman、Sougata Santra、Adinath Majee、Alakananda Hajra

  DOI：10.1002/adsc.201300298

  日期：2013.6.17

  A new copper‐catalyzed oxidative cyclization via CH amination between 2‐aminopyridines and methyl aryl/heteroaryl ketones has been developed under ambient air. Imidazo[1,2‐a]pyridines containing a wide range of functional groups have been synthesized from basic and easily available starting materials. This simple, one‐pot reaction protocol is applicable for the direct preparation of zolimidine (a

  一种新的铜催化的氧化环化经由Ç  ħ胺化2-氨基吡啶和间甲基芳基/杂芳基酮已根据环境空气显影。含有多种官能团的咪唑并[1,2- a ]吡啶是从碱性且容易获得的起始原料合成的。这种简单的一锅法反应方案适用于大规模直接制备唑来咪定（市售的抗溃疡药）。
• NIS mediated dehydrogenative-cyclocondensation in aqueous medium towards the synthesis of 2-arylimidazo[1,2-a]pyridines and their 3-formylated derivatives
  作者：Kousar Jahan、Firdoos Ahmad Sofi、Sumi Aisha Salim、Prasad V. Bharatam

  DOI：10.1016/j.tet.2022.132715

  日期：2022.4

  An environmental friendly, NIS mediated oxidative cyclocondensation of 2-aminopyridine and aryl methyl ketone/cinnamaldehydes has been realized for the synthesis of 2-arylimidazo [1,2-a]pyridines and their 3-formylated products respectively. This one pot protocol involves simple reaction conditions, tolerates wide range of substrates and the products were formed in good to excellent yields.

  已实现环境友好、NIS 介导的 2-氨基吡啶和芳基甲基酮/肉桂醛的氧化缩合反应，分别用于合成 2-芳基咪唑并 [1,2-a] 吡啶及其 3-甲酰化产物。这种一锅法涉及简单的反应条件，耐受范围广泛的底物，并且产品以良好至优异的产率形成。
• Rh(III)-Catalyzed Tandem Bicyclization of 2-Arylimidazo[1,2-<i>a</i>]pyridines with Cyclic Enones for the Construction of Bridged Scaffolds
  作者：K. Nagarjuna Reddy、D. Yogananda Chary、B. Sridhar、B. V. Subba Reddy

  DOI：10.1021/acs.orglett.9b03041

  日期：2019.11.1

  An efficient Rh(III)-catalyzed bicyclization of 2-arylimidazo[1,2-a]pyridine with cyclic enones has been developed for the synthesis of bridged imidazopyridine derivatives in excellent yields up to 95%. The reaction proceeds through a sequential conjugate addition of ortho-C-H bond of aryl group followed by an intramolecular C3-alkylation of imidazopyridine ring in a highly regioselective manner.

  已经开发了有效的Rh（III）催化2-芳基咪唑并[1,2-a]吡啶与环烯酮的双环化，用于合成桥接的咪唑并吡啶衍生物，产率高达95％。该反应通过依次共轭添加芳基的邻-CH键，然后以高度区域选择性的方式使咪唑并吡啶环的分子内C3-烷基化而进行。