CN104892494A - 一种4,4＇-二甲基-2,2＇-联吡啶的制备方法 - Google Patents

一种4,4＇-二甲基-2,2＇-联吡啶的制备方法 Download PDF

Info

Publication number
CN104892494A
CN104892494A CN201510291441.6A CN201510291441A CN104892494A CN 104892494 A CN104892494 A CN 104892494A CN 201510291441 A CN201510291441 A CN 201510291441A CN 104892494 A CN104892494 A CN 104892494A
Authority
CN
China
Prior art keywords
dimethyl
preparation
picoline
dipyridyl
add
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CN201510291441.6A
Other languages
English (en)
Other versions
CN104892494B (zh
Inventor
过治军
张玮玮
郭利兵
李玉江
许霞
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Henan Normal University
Original Assignee
Henan Normal University
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Henan Normal University filed Critical Henan Normal University
Priority to CN201510291441.6A priority Critical patent/CN104892494B/zh
Publication of CN104892494A publication Critical patent/CN104892494A/zh
Application granted granted Critical
Publication of CN104892494B publication Critical patent/CN104892494B/zh
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/22—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing two or more pyridine rings directly linked together, e.g. bipyridyl
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
    • C07D213/127—Preparation from compounds containing pyridine rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Catalysts (AREA)
  • Pyridine Compounds (AREA)

Abstract

本发明公开了一种4,4'-二甲基-2,2'-联吡啶的制备方法，属于太阳能电池光敏催化剂的合成技术领域。本发明的技术方案要点为：（1）将4-甲基吡啶置于反应容器中并加入醋酸溶解，分两次加入质量浓度为30%的双氧水，然后于室温下进行氧化反应制得N-氧化吡啶；（2）加入钯碳催化剂并升温至60-80℃回流使N-氧化吡啶发生偶联反应，再加入三氯化磷进行脱氧，然后减压抽滤滤去不溶物，将滤液减压蒸去溶剂后得到白色晶体4,4'-二甲基-2,2'-联吡啶。本发明直接利用吡啶环上N原子被氧化的4-甲基吡啶氧化物作为中间体，再用钯碳催化偶联，用三氯化磷脱氧，省去了卤代吡啶的合成，节约了生产成本，而且该方法产率较高，适用于工业化生产。

Description

一种4,4＇-二甲基-2,2＇-联吡啶的制备方法
技术领域
本发明属于太阳能电池光敏催化剂的合成技术领域，具体涉及一种4,4'-二甲基-2,2'-联吡啶的制备方法。
背景技术
当今，缺电子的六元杂环化合物是一类非常重要的有机物，其中含氮杂环化合物，如吡啶以及吡啶衍生物是比较重要的一类。含氮杂环化合物由于其水溶性较大，结构稳定以及其独特的生物活性、低毒性和高内吸性，常被用于医药和农药的结构单元，广泛应用于医药、农药、染料和橡胶制品等工业领域。此外，含氮杂环化合物作为π电子共轭杂环和刚性平面的化合物，具有强烈的荧光效应，能用于染料和太阳能电池。太阳能电池作为一种清洁且环境无污染的新型电池，其研究对于环境保护具有重要的意义。吡啶是最基本、最典型的含氮六元杂环芳香化合物，吡啶以及吡啶衍生物被广泛作为太阳能电池光敏催化剂进行研究。研究结果表明，随着π电子共轭体系的增大，分子的荧光效应也会大大增强，可提高光电转换效率。因此合成吡啶的大共轭体系具有重要的意义。
Hasson等人以卤代吡啶为原料，以钯等过渡金属络合物为催化剂，合成得到了联吡啶。但是若要合成4,4’-二甲基-2,2’-联吡啶，需要首先制得4-甲基-2-氯吡啶，增加了反应步骤和生产成本。吴晓宏等人以4-甲基吡啶为原料、钯碳为催化剂，直接制备了4,4’-二甲基-2,2’-联吡啶，该制备方法虽然反应简单，产品纯度也较高，但是该方法制得的4,4’-二甲基-2,2’-联吡啶的收率为72.7%，收率相对较低，不能直接用于工业生产，因此限制了该方法的现实应用。
4,4’-二甲基-2,2’-联吡啶因具有N和O两种配体，能与多种金属离子形成配合物，在化工合成和太阳能电池光敏催化剂中应用广泛，因此研究该化合物的新型高效的合成方法具有重要的应用价值和现实意义。
发明内容
本发明解决的技术问题是提供了一种操作简单且产率较高的4,4'-二甲基-2,2'-联吡啶的制备方法，该方法原料简单易得，反应步骤较少，产物收率较高，适于大规模工业化生产。
本发明为解决上述技术问题采用如下技术方案，一种4,4'-二甲基-2,2'-联吡啶的制备方法，其特征在于包括以下步骤：（1）将4-甲基吡啶置于反应容器中并加入醋酸溶解，分两次加入质量浓度为30%的双氧水(保持氧化的浓度，防止浓度过高出现危险)，然后于室温下进行氧化反应制得N-氧化吡啶；（2）加入钯碳催化剂并升温至60-80℃回流使N-氧化吡啶发生偶联反应，再加入三氯化磷进行脱氧，然后减压抽滤滤去不溶物，将滤液减压蒸去溶剂后得到白色晶体，该白色晶体用乙酸乙酯重结晶和纯化后制得4,4'-二甲基-2,2'-联吡啶。
进一步限定，制备过程中1g 4-甲基吡啶对应质量浓度为30%的双氧水16-32mL。
进一步限定，制备过程中4-甲基吡啶与钯碳催化剂的质量比为1:0.0012-0.025。
进一步限定，制备过程中1g 4-甲基吡啶对应醋酸10-20mL。
进一步限定，制备过程中4-甲基吡啶与三氯化磷的摩尔比为1:1-1.2。
本发明与现有技术相比具有以下有益效果：（1）反应体系简单，仅使用醋酸和质量浓度为30%的双氧水这些普通试剂，成本相对低廉；（2）操作简单，只需要回流一次和重结晶一次，而且耗时较少，获得产物的效率较高，适于大规模生产。本发明直接利用吡啶环上N原子被氧化的4-甲基吡啶氧化物作为中间体，再用钯碳催化偶联，用三氯化磷脱氧，省去了卤代吡啶的合成，节约了生产成本，而且该方法产率较高，适用于工业化生产。
具体实施方式
以下通过实施例对本发明的上述内容做进一步详细说明，但不应该将此理解为本发明上述主题的范围仅限于以下的实施例，凡基于本发明上述内容实现的技术均属于本发明的范围。
实施例1
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入10mL醋酸溶解原料，分两次加入15mL质量浓度为30%的双氧水，于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0012g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入145g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.7720g，收率83.8%。
实施例2
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入10mL醋酸溶解原料，分两次加入15mL质量浓度为30%的双氧水，于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0059g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入145g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.7812g，收率84.8%。
实施例3
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入10mL醋酸溶解原料，分两次加入15mL质量浓度为30%的双氧水，于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0118g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入137g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.8678g，收率94.2%。
实施例4
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入10mL醋酸溶解原料，分两次加入15mL质量浓度为30%的双氧水。于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0237g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入137g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.8614g，收率94.6%。
实施例5
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入15mL醋酸溶解原料，分两次加入15mL质量浓度为30%的双氧水。于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0118g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入165g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.8585g，收率93.2%。
实施例6
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入20mL醋酸溶解原料，分两次加入15mL质量浓度为30%的双氧水。于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0118g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入165g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.8972g，收率97.4%。
实施例7
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入20mL醋酸溶解原料，分两次加入20mL质量浓度为30%的双氧水。于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0118g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入145g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.8935g，收率97.0%。
实施例8
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入20mL醋酸溶解原料，分两次加入25mL质量浓度为30%的双氧水。于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0118g钯碳催化剂，于65℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入145g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.8825g，收率95.8%。
实施例9
称取0.93g分析纯的4-甲基吡啶，加入到反应瓶中，再加入20mL醋酸溶解原料，分两次加入30mL质量浓度为30%的双氧水。于室温下静置，使4-甲基吡啶发生氧化反应。3.5h后，加入0.0118g钯碳催化剂，于75℃油浴下，加热回流反应。大约6h后，停止反应。待反应液冷却至室温后，加入145g三氯化磷进行脱氧，然后使用布氏漏斗对反应瓶内液体进行减压抽滤操作，滤去不溶物质。将滤液减压蒸去溶剂，所得剩余物为白色晶体。将该白色晶体用20mL乙酸乙酯进行重结晶。将所得晶体真空干燥。称重，所得4,4’-二甲基-2,2’-联吡啶0.8696g，收率94.4%。
图谱数据
目标产物4,4’-二甲基-2,2’-联吡啶的结构为：
1H-NMR (DMSO, 300 MHz) δ: 2.40 (s, 6H, 2CH3), 7.27 (d, J＝4.9 Hz, 2H, H-5, H-5'), 8.22 (s, 2H, H-3, H-3'), 8.54 (d, J＝4.9 Hz, 2H, H-6, H-6')。
元素分析
4,4’-二甲基-2,2’-联吡啶（分子式C12H12N2）计算值：C 78.26，H 6.52，N 15.22；分析值：C 78.28，H 6.88，N 14.87。
以上实施例描述了本发明的基本原理、主要特征及优点，本行业的技术人员应该了解，本发明不受上述实施例的限制，上述实施例和说明书中描述的只是说明本发明的原理，在不脱离本发明原理的范围下，本发明还会有各种变化和改进，这些变化和改进均落入本发明保护的范围内。

Claims (5)

1.一种4,4'-二甲基-2,2'-联吡啶的制备方法，其特征在于包括以下步骤：（1）将4-甲基吡啶置于反应容器中并加入醋酸溶解，分两次加入质量浓度为30%的双氧水，然后于室温下进行氧化反应制得N-氧化吡啶；（2）加入钯碳催化剂并升温至60-80℃回流使N-氧化吡啶发生偶联反应，再加入三氯化磷进行脱氧，然后减压抽滤滤去不溶物，将滤液减压蒸去溶剂后得到白色晶体，该白色晶体用乙酸乙酯重结晶和纯化后制得4,4'-二甲基-2,2'-联吡啶。
2.根据权利要求1所述的4,4'-二甲基-2,2'-联吡啶的制备方法，其特征在于：制备过程中1g 4-甲基吡啶对应质量浓度为30%的双氧水16-32mL。
3. 根据权利要求1所述的4,4'-二甲基-2,2'-联吡啶的制备方法，其特征在于：制备过程中4-甲基吡啶与钯碳催化剂的质量比为1:0.0012-0.025。
4. 根据权利要求1所述的4,4'-二甲基-2,2'-联吡啶的制备方法，其特征在于：制备过程中1g 4-甲基吡啶对应醋酸10-20mL。
5. 根据权利要求1所述的4,4'-二甲基-2,2'-联吡啶的制备方法，其特征在于：制备过程中4-甲基吡啶与三氯化磷的摩尔比为1:1-1.2。
CN201510291441.6A 2015-06-01 2015-06-01 一种4,4＇‑二甲基‑2,2＇‑联吡啶的制备方法 Expired - Fee Related CN104892494B (zh)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201510291441.6A CN104892494B (zh) 2015-06-01 2015-06-01 一种4,4＇‑二甲基‑2,2＇‑联吡啶的制备方法

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201510291441.6A CN104892494B (zh) 2015-06-01 2015-06-01 一种4,4＇‑二甲基‑2,2＇‑联吡啶的制备方法

Publications (2)

Publication Number Publication Date
CN104892494A true CN104892494A (zh) 2015-09-09
CN104892494B CN104892494B (zh) 2017-08-11

Family

ID=54025513

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201510291441.6A Expired - Fee Related CN104892494B (zh) 2015-06-01 2015-06-01 一种4,4＇‑二甲基‑2,2＇‑联吡啶的制备方法

Country Status (1)

Country Link
CN (1) CN104892494B (zh)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102199120A (zh) * 2011-04-01 2011-09-28 聊城大学 一种2,2'-联吡啶-4,4'-二甲酸的合成方法
CN102731487A (zh) * 2011-04-01 2012-10-17 季昀 衍生自4,4’-二酸-2,2’-双吡啶的三牙配位子、金属错合物及其应用
WO2012153253A2 (en) * 2011-05-06 2012-11-15 Jan Gysbert Hermanus Du Preez Aromatic compounds and metal complexes thereof
WO2013076197A1 (en) * 2011-11-22 2013-05-30 Solvay Sa Dye compounds, method of making the same, and their use in dye-sensitized solar cells

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102199120A (zh) * 2011-04-01 2011-09-28 聊城大学 一种2,2'-联吡啶-4,4'-二甲酸的合成方法
CN102731487A (zh) * 2011-04-01 2012-10-17 季昀 衍生自4,4’-二酸-2,2’-双吡啶的三牙配位子、金属错合物及其应用
WO2012153253A2 (en) * 2011-05-06 2012-11-15 Jan Gysbert Hermanus Du Preez Aromatic compounds and metal complexes thereof
WO2013076197A1 (en) * 2011-11-22 2013-05-30 Solvay Sa Dye compounds, method of making the same, and their use in dye-sensitized solar cells

Non-Patent Citations (10)

* Cited by examiner, † Cited by third party
Title
FRANK W. LEWIS,等: "Synthesis and Evaluation of Lipophilic BTBP Ligands for An/Ln Separation in Nuclear Waste Treatment: The Effect of Alkyl Substitution on Extraction Properties and Implications for Ligand Design", 《EUR. J. ORG. CHEM.》 *
HAGINIWA, JOJU，等: "Reactions concerned in tertiary amine N-oxides. XII.The synthesis of asymmetric compounds containing the ferroin or cuproin group", 《YAKUGAKU ZASSHI》 *
HAGINIWA, JOJU，等: "Reactions concerning tertiary amine N-oxides. II. Reactions of pyridine and quinoline series with their N-oxides", 《YAKUGAKU ZASSHI》 *
HAGINIWA, JOJU，等: "Reactions of tertiary amine N-oxides. V. Preparation of asymmetric 2,2"-dipyridyl, 2,2"pyridylquinoline, and pyridylphenanthroline derivatives", 《YAKUGAKU ZASSHI》 *
JOSEPH A.BUONOMO,等: "Substituted 2,2"-Bipyridines by Nickel Catalysis: 4,4′-Di-tert-butyl-2,2′-bipyridine", 《SYNTHESIS》 *
KATSUHIRO SUMI，等: "Preparation and Luminescence Properties of Tris( Bipyridine) Ruthenium (II)-Containing Vinyl Polymers: Ru(bpy)2 (Po1y-6-Vinyl-2,2‘-Bipyridine)Cl2 and Ru(bpy)2(Poly-4-Methy1-4’-Vinyl- 2,2’- Bipyridine)Cl2", 《JOURNAL OF POLYMER SCIENCE: POLYMER CHEMISTRY EDITION》 *
SASA DURIC，等: "Synthesis of Unsymmetrically Substituted Bipyridines by Palladium-Catalyzed Direct C-H Arylation of Pyridine N-Oxides", 《ORGANIC LETTERS》 *
TUBA GÜDEN-SILBER，等: "4,4’-Bis(trifluoromethyl)-2,2’-bipyridine –a multipurpose ligand scaffold for lanthanoidbased luminescence/19F NMR probes", 《DALTON TRANS.》 *
VELI-MATTI MUKKALA，等: "119. New 2,2"-Bipyridine Derivatives and Their Luminescence Properties with Europiurn(III) and Terbiurn(III) Ions)", 《HELVETICA CHIMICA ACTA》 *
WEI LIU，等: "Pd-Catalyzed Oxidative CH/CH Direct Coupling of Heterocyclic N‑Oxides", 《ORGANIC LETTERS》 *

Also Published As

Publication number Publication date
CN104892494B (zh) 2017-08-11

Similar Documents

Publication Publication Date Title
Maurya et al. Synthesis, characterization, reactivity, and catalytic potential of model vanadium (IV, V) complexes with benzimidazole-derived ONN donor ligands
Ngan et al. Dinuclear and polynuclear dioxomolybdenum (VI) Schiff base complexes: Synthesis, structural elucidation, spectroscopic characterization, electrochemistry and catalytic property
Kopylovich et al. Alkoxy‐1, 3, 5‐triazapentadien (e/ato) Copper (II) Complexes: Template Formation and Applications for the Preparation of Pyrimidines and as Catalysts for Oxidation of Alcohols to Carbonyl Products
Lukoyanov et al. Novel oxidovanadium complexes with redox-active r-mian and r-bian ligands: synthesis, structure, redox and catalytic properties
Askarizadeh et al. Tailoring dicobalt Pacman complexes of Schiff-base calixpyrroles towards dioxygen reduction catalysis
CN103232365A (zh) 一种西弗碱类化合物、合成方法及用途
Asha et al. Dioxidomolybdenum (VI) complexes chelated with N4-(3-methoxyphenyl) thiosemicarbazone as molybdenum (IV) precursors in oxygen atom transfer process and oxidation of styrene
CN103333331A (zh) 一种高分子负载型催化剂及其制备方法和应用
El-Sonbati et al. Polymer complexes XXXVII novel models and structural of symmetrical poly-Schiff base on heterobinuclear complexes of dioxouranium (VI)
CN114478648A (zh) 一种类吡啶吡咯钌配合物及其制备方法和作为电催化氨氧化催化剂的应用
Ramadan et al. New mononuclear copper (I) and copper (II) complexes containing N4 donors; crystal structure and catechol oxidase biomimetic catalytic activity
CN104098607A (zh) 含三环己基膦的单膦单氮杂环卡宾镍(ii)配合物及其应用
Ghosh et al. Reductive nitrosylation and proton-assisted bridge splitting of a (μ-oxo) dimanganese (III) complex derived from a polypyridine ligand with one carboxamide group
CN103172479B (zh) 一种钯催化的联芳烃制备方法
CN113307804A (zh) 含氟吲哚喹啉类化合物的合成方法及其应用
CN104892494A (zh) 一种4,4＇-二甲基-2,2＇-联吡啶的制备方法
Chambers et al. Synthesis and characterization of alkoxycarbonyl cobalt complexes via direct carbonylation methods
CN107501338B (zh) 一种2,6-二氨基吡啶缩4-羧基苯甲醛双希夫碱钴配合物的制备方法
Lawal et al. Oxidation of Styrene to Benzaldehyde Catalyzed by Schiff Base Functionalized Triazolylidene Ni (II) Complexes
CN105294540A (zh) 一种以三苯胺为中心的新型希夫碱化合物及其制备
CN113121458B (zh) 一种超声波辐射催化快速合成2,3-二氨基吩嗪的方法
CN105272987A (zh) 一种3-氰基-n-错位卟啉化合物的制备方法
Thallaj et al. Steric Congestion at, and Proximity to, a Ferrous Center Leads to Hydration of α-Nitrile Substituents Forming Coordinated Carboxamides
Zucca et al. Pt (II) derivatives with rollover-coordinated 6-substituted 2, 2′-bipyridines: Ligands with multiple personalities
CN102977040B (zh) 一种2-喹喔啉基二甲缩醛和2-喹喔啉基甲醛的合成方法

Legal Events

Date Code Title Description
C06 Publication
PB01 Publication
C10 Entry into substantive examination
SE01 Entry into force of request for substantive examination
GR01 Patent grant
GR01 Patent grant
CF01 Termination of patent right due to non-payment of annual fee
CF01 Termination of patent right due to non-payment of annual fee

Granted publication date: 20170811

Termination date: 20200601