2-(pyridin-3-yl)-5-(3,4-methylenedioxyphenyl)oxazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并间二氧杂环戊烯类
• 英文名称: 2-(pyridin-3-yl)-5-(3,4-methylenedioxyphenyl)oxazole
• 英文别名: 5-(benzo[d][1,3]dioxol-5-yl)-2-(pyridin-3-yl)oxazole；texaline；5-(1,3-benzodioxol-5-yl)-2-pyridin-3-yl-1,3-oxazole
• 化学式: C₁₅H₁₀N₂O₃
• 分子量: 266.256
• InChiKey: SDHIXARCLVIOJM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  57.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3,4-亚甲二氧苯乙酮 在 palladium on activated charcoal N-溴代丁二酰亚胺(NBS) 、 sodium azide 、 硫酸 、 氢气 、 乙酸酐 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 溶剂黄146 、 二甲基亚砜 、 乙酸乙酯 、 乙腈 为溶剂， 90.0 ℃ 、101.33 kPa 条件下， 生成 2-(pyridin-3-yl)-5-(3,4-methylenedioxyphenyl)oxazole
  参考文献：
  名称：

  Antimycobacterial natural products: synthesis and preliminary biological evaluation of the oxazole-containing alkaloid texaline

  摘要：

  Texaline, an antimycobacterial oxazole-containing alkaloid previously isolated from Amyris texana and A. elemifera, and related compounds have been synthesized in order to explore aspects of the structure-anti tuberculosis activity relationship. While texaline was found to be inactive in our assays, simpler diaryloxazoles were more active whilst also exhibiting modest toxic selectivity, leading to their identification as potential lead compounds. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.08.119

文献信息

• Synthesis of Substituted Oxazoles by Visible-Light Photocatalysis
  作者：Tanmay Chatterjee、Ji Young Cho、Eun Jin Cho

  DOI：10.1021/acs.joc.6b00989

  日期：2016.8.19

  A simple and practical method for the synthesis of substituted oxazoles has been developed using readily available α-bromoketones and benzylamines by visible-light photocatalysis at room temperature. The process, which requires 1 mol % of [Ru(bpy)3]Cl2 photocatalyst with K3PO4 and CCl3Br, is effective for accessing a variety of valuable oxazole compounds. The synthetic utility of our protocol was also

  已经开发了一种简单而实用的合成取代的恶唑的方法，该方法使用易得的α-溴代酮和苄胺，在室温下通过可见光光催化进行合成。该方法需要1摩尔％的具有K 3 PO 4和CCl 3 Br的[Ru（bpy）3 ] Cl 2光催化剂，可有效地获得各种有价值的恶唑化合物。我们的协议的合成效用也通过制备天然产物texaline得到了证明。
• Mild Palladium-Catalyzed Regioselective Direct Arylation of Azoles Promoted by Tetrabutylammonium Acetate
  作者：Fabio Bellina、Marco Lessi、Chiara Manzini

  DOI：10.1002/ejoc.201300704

  日期：2013.9

  A mild, general, and convenient palladium-catalyzed direct arylation of the 5-position of azoles with aryl bromides, efficiently promoted by tetrabutylammonium acetate, is described. 1-Methylpyrazole, oxazole, and thiazole reacted at 70 °C in N,N-dimethylacetamide by using Pd(OAc)2 as the catalyst precursor. Electron-poor and -rich functional groups, including the free hydroxy group, are well tolerated

  描述了一种温和、通用且方便的钯催化的 5-位唑类与芳基溴化物的直接芳基化反应，由乙酸四丁铵有效促进。通过使用 Pd(OAc)2 作为催化剂前体，1-甲基吡唑、恶唑和噻唑在 N,N-二甲基乙酰胺中在 70 °C 下反应。贫电子和富电子官能团，包括游离羟基，在亲电伙伴中具有良好的耐受性。通过将反应温度提高到 110 °C，也可以非常有效地获得各种 5-芳基-1-甲基咪唑。这种无配体方案已成功应用于两种生物活性天然化合物 balsoxin 和 texaline 的一锅合成，从恶唑开始，通过 5 位和 2 位的顺序直接芳基化。
• Palladium-Catalyzed Direct (Hetero)arylation of Ethyl Oxazole-4-carboxylate: An Efficient Access to (Hetero)aryloxazoles
  作者：Cécile Verrier、Thibaut Martin、Christophe Hoarau、Francis Marsais

  DOI：10.1021/jo801093n

  日期：2008.9.19

  toward 2-(hetero)arylated and 2,5-di(hetero)arylated oxazoles through regiocontrolled palladium-catalyzed direct (hetero)arylation of ethyl oxazole-4-carboxylate with iodo-, bromo-, and chloro(hetero)aromatics followed by a two-step hydrolysis/decarboxylation sequence was described. The method was applied here to a neat synthesis of two 2,5-di(hetero)aryloxazole natural products, balsoxin and texaline

  通过区域控制的钯催化的恶唑-4-羧酸乙酯与碘，溴和氯（杂）的直接（杂）芳基化反应，生成2-（杂）芳基化和2,5-二（杂）芳基恶唑的直接途径描述了芳族化合物，随后是两步水解/脱羧序列。该方法在这里用于两种2,5-二（杂）芳基恶唑天然产物balsoxin和texaline的纯净合成。
• Direct arylations on water: synthesis of 2,5-disubstituted oxazoles balsoxin and texaline
  作者：Stephan A. Ohnmacht、Patrizia Mamone、Andrew J. Culshaw、Michael F. Greaney

  DOI：10.1039/b719466h

  日期：——

  An efficient two-step palladium catalysed synthesis of 2,5-disubstituted oxazoles is reported.

  报告了一种高效的二步钯催化合成2,5-二取代恶唑的方法。
• Nickel-Catalyzed CH Arylation of Azoles with Haloarenes: Scope, Mechanism, and Applications to the Synthesis of Bioactive Molecules
  作者：Takuya Yamamoto、Kei Muto、Masato Komiyama、Jérôme Canivet、Junichiro Yamaguchi、Kenichiro Itami

  DOI：10.1002/chem.201101091

  日期：2011.8.29

  Novel nickel‐based catalytic systems for the CH arylation of azoles with haloarenes and aryl triflates have been developed. We have established that Ni(OAc)2/bipy/LiOtBu serves as a general catalytic system for the coupling with aryl bromides and iodides as aryl electrophiles. For couplings with more challenging electrophiles, such as aryl chlorides and triflates, the Ni(OAc)2/dppf (dppf=1,1′‐bis

  对于C新颖的镍基催化体系与卤代芳烃和芳基三氟甲磺酸酯唑h的芳基化得到了发展。我们已经确定，Ni（OAc）2 / bipy / LiO t Bu用作与芳基溴化物和碘化物作为芳基亲电子试剂偶联的一般催化体系。对于与更具挑战性的亲电试剂（例如芳基氯化物和三氟甲磺酸酯）偶联，发现Ni（OAc）2 / dppf（dppf = 1,1'-bis（diphenylphosphino）ferrocene）系统是有效的。噻唑，苯并噻唑，恶唑，苯并恶唑和苯并咪唑可用作杂芳烃偶联伴侣。经过进一步研究，我们发现了使用Mg（O t Bu）2进行本偶联的新方案作为LiO t Bu的温和且便宜的替代品。还描述了试图揭示这种镍催化的杂联芳基偶联机理的尝试。该新开发的方法已成功应用于非布索坦（一种有效治疗痛风和高尿酸血症的黄嘌呤氧化酶抑制剂），他法米第（一种有效治疗TTR淀粉样蛋白多神经病的药物）和texaline（一种天然的抗结核药物）的合成活动）。

表征谱图