CN111499566A - 一种吡啶衍生物化合物及其制备方法 - Google Patents

一种吡啶衍生物化合物及其制备方法 Download PDF

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CN111499566A
CN111499566A CN202010363572.1A CN202010363572A CN111499566A CN 111499566 A CN111499566 A CN 111499566A CN 202010363572 A CN202010363572 A CN 202010363572A CN 111499566 A CN111499566 A CN 111499566A
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phosphonium salt
quaternary phosphonium
derivative compound
pyridine
pyridine derivative
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车媛媛
冯超
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Nanjing Tech University
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Nanjing Tech University
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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

本发明公开了一种吡啶衍生物化合物及其制备方法。本发明通过在惰性气体氛围下，将杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体依次加入到溶剂中，得到混合物，其中，所述杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体的摩尔比为2.5～25：1～10：3～30：1.2～12：0.5％～5％：1％～10％，所述碘化物与溶剂的摩尔体积比为0.1mmol：1mL；然后，在惰性气体氛围下，将所述混合物在62～68℃温度下反应11～13小时，收集反应产物为吡啶衍生物化合物。本发明制备方法所采用的原材料简单易得，底物范围广，成本低，反应条件温和，并且催化剂用量极少。

Description

一种吡啶衍生物化合物及其制备方法
技术领域
本发明属于有机化学合成技术领域，尤其涉及一种吡啶衍生物化合物及其制备方法。
背景技术
基于吡啶和二嗪等氮杂环的吡啶衍生物化合物是重要的药效基团，广泛存在于生物活性化合物、药物、功能材料和配体中，有很重要的实用价值。因此，学术界和工业界都对其合成方法有着很高的要求和浓厚的兴趣，目前实现吡啶官能团化的方法主要有以下三种策略：
(1)通过C-H键活化直接将氮杂环官能化，是将不同基团选择性引入的有效手段。如文献1(Yoshiaki Nakao,Kyalo Stephen Kanyiva,TamejiroHiyama.J.Am.Chem.Soc.2008,130，2448-2449)所公开的方法中，吡啶的氮原子与路易斯酸配位导致氮缺电子，使二号位氢键酸度增加，从而起到活化C-H键的作用，实现吡啶烯基化，具体的反应过程如下所示：
Figure BDA0002475806620000011
(2)Minisci反应是将含碳基团与氮杂芳烃偶联的有效手段，其主要特征为碳自由基进攻氮杂芳烃，完成氮杂芳烃的C-H键官能团化。如文献2(Jian Jin,David W C Macmillan.Angew.Chem.Int.Ed.2014,53，1-6)所公开的方法中，在光催化下，环氧烷基自由基与缺电子的杂芳烃反应实现官能团化，具体的反应过程如下所示：
Figure BDA0002475806620000021
(3)金属催化的交叉偶联是制备杂联芳基的主要方法。(杂)芳基卤化物可以与(杂)芳基试剂，例如硼酸、有机锡试剂、有机锌试剂和格氏试剂区域选择性的偶联。如文献3(Christophe Coudret,Valerie Mazenc.Tetrahedron Letters.1997,38，5293-5296)所公开的方法中，4-吡啶硼酸酯与卤代烃的交叉偶联反应，具体的反应过程如下所示：
Figure BDA0002475806620000022
但是，以上几种策略均存在不同程度的局限性，包括反应选择性不好、适用范围狭窄、原料合成困难等问题，因而很难应用到生产中。
发明内容
本发明的目的在于提供一种吡啶衍生物化合物及其制备方法，旨在解决上述背景技术中现有技术所存在的各种不足。
本发明是这样实现的，一种吡啶衍生物化合物，该化合物的化学结构式如下式(Ⅰ)所示：
Figure BDA0002475806620000023
式(Ⅰ)中，被R1取代的苯基为4-甲氧基苯基、3,5-二氟苯基、3-叔丁基苯基、3-溴苯基、2-氯苯基、2,6-二甲基苯基、萘基、苯并呋喃基、联苯基、4-甲酸甲酯苯基、4-三氟甲基苯基、4-硝基苯基、4-氰基苯基、4-乙酰基苯基、4-乙酰胺苯基、4-三甲基硅基苯基、苯并二氧五环基、3,5-二甲基异恶唑基、N-甲基吡唑基、N-苯基咔唑基、噻吩基、三异丙基硅基乙炔基、3,4-二氢萘基、苯甲酸香叶酯基、苯甲酸薄荷酯基、雌酚酮衍生物、布洛芬衍生物以及生育酚衍生物中的任意一种；
被R2取代的氮杂环基团为2-氟吡啶、2-氯吡啶、2-苯基吡啶、2,3-环己基吡啶、3-甲基吡啶、3-甲氧基吡啶、3-苯基吡啶、3-氟吡啶、3-甲酸甲酯基吡啶、3-氰基吡啶、N-甲基-7-氮杂吲哚、吡丙醚、比沙可啶、3-(1-二苯甲基氮杂环丁基-3-甲氧基甲基)吡啶、1-苯磺酰基-4-吡啶基哌嗪、(2-(4-甲氧基苯基)-4-(三氟甲基)吡啶、2-氯-5-乙基-4-(4-甲氧基苯基)嘧啶、2-(4-甲氧基苯基)吡嗪、5-(4-甲氧基苯基)-2,3-二甲基吡嗪、辛可尼丁、4-氟-4'-甲氧基-1,1'-联苯、4-甲酸甲酯-4'-甲氧基-1,1'-联苯以及4-三氟甲基-4'-甲氧基-1,1'-联苯)中的任意一种。
本发明进一步公开了上述吡啶衍生物化合物的制备方法，该方法包括以下步骤：
(1)在惰性气体氛围下，将杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体依次加入到溶剂中，得到混合物，其中，所述杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体的摩尔比为2.5～25：1～10：3～30：1.2～12：0.5％～5％：1％～10％，所述碘化物与溶剂的摩尔体积比为0.1mmol：1mL；
(2)在惰性气体氛围下，将步骤(1)中得到的混合物在62～68℃温度下反应11～13小时，收集反应产物为吡啶衍生物化合物。
优选地，在步骤(1)中，所述杂环季膦盐为4-吡啶季膦盐、2-氟吡啶-4-季膦盐、2-氯吡啶-4-季膦盐、2-苯基吡啶-4-季膦盐、2,3-环己基吡啶-4-季膦盐、3-甲基吡啶-4-季膦盐、3-甲氧基吡啶-4-季膦盐、3-苯基吡啶-4-季膦盐、3-氟吡啶-4-季膦盐、3-甲酸甲酯基吡啶-4-季膦盐、3-氰基吡啶-4-季膦盐、N-甲基-7-氮杂吲哚-4-季膦盐、吡丙醚季膦盐、比沙可啶季膦盐、3-(1-二苯甲基氮杂环丁基-3-甲氧基甲基)吡啶季膦盐、1-苯磺酰基-4-吡啶基哌嗪季膦盐、4-三氟甲基吡啶-2-季膦盐、2-氯-5-乙基-4-嘧啶季膦盐、2-吡嗪季膦盐、2,3-二甲基吡嗪-5-季膦盐、辛可尼丁季膦盐、4-氟苯季膦盐、4-甲酸甲酯苯基季膦盐以及4-三氟甲基苯基季膦盐中的至少一种。
优选地，在步骤(1)中，所述碘化物为4-甲氧基碘苯、3,5-二氟碘苯、3-叔丁基碘苯、3-溴碘苯、2-氯碘苯、2,6-二甲基碘苯、碘化萘、碘代苯并呋喃、碘代联苯、4-甲酸甲酯碘苯、4-三氟甲基碘苯、4-硝基碘苯、4-氰基碘苯、4-乙酰基碘苯、4-乙酰胺碘苯、4-三甲基硅基碘苯、碘代苯并二氧五环、3,5-二甲基碘代异恶唑、N-甲基碘代吡唑、N-苯基碘代咔唑、碘代噻吩、三异丙基硅基碘代乙炔、3,4-二氢碘化萘、4-碘苯甲酸香叶酯、4-碘苯甲酸薄荷酯、碘代雌酚酮衍生物、碘代布洛芬衍生物以及碘代生育酚衍生物中的至少一种。
优选地，在步骤(1)中，所述碱为碳酸钾；所述添加剂为高氯酸银；所述钯催化剂为醋酸钯；
所述膦配体为2-二环己基膦-2’,6’-二异丙氧基-1,1’-联苯或者二苯基环己基膦；
所述溶剂为丙酮。
优选地，在步骤(1)中，所述杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体的摩尔比为2.5：1：3：1.2：0.5％：1％。
优选地，所述惰性气体为氮气。
2016年，McNally课题组首次报道了一种通过将吡啶和二嗪转化为杂环季膦盐的简便方法来实现进行吡啶4号位的官能化。该种方法具有简便、廉价、完全的区域选择性和较为广泛的适用性。如文献4(Xuan Zhang,Andrew Mcnally.Angew.Chem.Int.Ed.2017,56，9833-9836.)所公开的方法中，2017年，McNally课题组实现了杂环季膦盐与芳基硼酸在镍催化下生成杂联芳基，尽管在很大程度上克服了以往的困难，但是芳基硼酸与卤化物相比种类更少、更难获得，因而很难真正的应用于工业界。具体反应过程如下所示：
Figure BDA0002475806620000051
在此研究背景下，本发明克服现有技术的不足，提供一种吡啶衍生物化合物及其制备方法，本发明将杂环季膦盐作为亲核前体，以促进与(杂)芳基卤化物的偶联反应，在反应过程中，通过使用银添加剂稳定亲核负离子，减少质子化副反应的发生，以提高后续反应的产率；其中，该反应中所述卤化物种类繁多，结构多样，两种原料均简便易得，该策略的实现能够在研究和生产领域提供良好的基础。
相比于现有技术的缺点和不足，本发明具有以下有益效果：本发明制备方法所采用的原材料简单易得，底物范围广，成本低，反应条件温和，并且催化剂用量极少。
具体实施方式
为了使本发明的目的、技术方案及优点更加清楚明白，以下结合实施例，对本发明进行进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。
实施例1
(1)在氮气氛围下，将0.25mmol 4-吡啶季膦盐、0.1mmol 4-甲氧基碘苯、0.3mmol碳酸钾、0.12mmol的高氯酸银、0.005mmol醋酸钯、0.01mmol的2-二环己基膦-2’,6’-二异丙氧基-1,1’-联苯依次加入到1.0mL丙酮中，得到混合物；
(2)在氮气氛围下，将步骤(1)中所得的混合物在65℃的反应温度下反应12小时，再从反应产物中收集出吡啶衍生物化合物1。
实施例2
(1)在氮气氛围下，将0.25mmol 3-甲氧基吡啶-4-季膦盐、0.1mmol 4-甲氧基碘苯、0.3mmol碳酸钾、0.12mmol的高氯酸银、0.005mmol醋酸钯、0.02mmol二苯基环己基膦依次加入到1.0mL丙酮中，得到混合物；
(2)在氮气氛围下，将步骤(1)中所得的混合物在65℃的反应温度下反应12小时，再从反应产物中收集出吡啶衍生物化合物2。
实施例3
(1)在氮气氛围下，将0.25mmol 4-三氟甲基吡啶-2-季膦盐、0.1mmol 4-甲氧基碘苯、0.3mmol碳酸钾、0.12mmol的高氯酸银、0.005mmol醋酸钯、0.05mmol二苯基环己基膦依次加入到1.0mL丙酮中，得到混合物；
(2)在氮气氛围下，将步骤(1)中所得的混合物在65℃的反应温度下反应12小时，再从反应产物中收集出吡啶衍生物化合物3。
实施例4
(1)在氮气氛围下，将0.25mmol 4-氟苯季膦盐、0.1mmol 4-甲氧基碘苯、0.3mmol碳酸钾、0.12mmol的高氯酸银、0.005mmol醋酸钯、0.01mmol三苯基膦依次加入到1.0mL丙酮中，得到混合物；
(2)在氮气氛围下，将步骤(1)中所得的混合物在40℃的反应温度下反应12小时，再从反应产物中收集出联苯化合物4。
实施例5
实施例5～41与实施例1基本相同，差别之处如下表1所示：
表1实施例5～41与实施例1的不同之处列表
Figure BDA0002475806620000061
Figure BDA0002475806620000071
Figure BDA0002475806620000081
实施例42～46
实施例42～46与实施例2基本相同，差别之处如下表2所示：
表2实施例42～46与实施例2的不同之处列表
Figure BDA0002475806620000082
Figure BDA0002475806620000091
实施例47～50
实施例47～50与实施例3基本相同，差别之处如下表3所示：
表3实施例47～50与实施例3的不同之处列表
Figure BDA0002475806620000092
实施例51～52
实施例51～52与实施例3基本相同，差别之处如下表4所示：
表4实施例51～52与实施例3的不同之处列表
实施例编号 杂环季膦盐 碘化物 合成化合物编号
51 4-甲酸甲酯苯基季膦盐 4-甲氧基碘苯 51
52 4-三氟甲基苯基季膦盐 4-甲氧基碘苯 52
实施例53
(1)在氮气氛围下，将2.5mmol 4-吡啶季膦盐、1mmol 4-甲氧基碘苯、3mmol碳酸钾、1.2mmol的高氯酸银、0.005mmol醋酸钯、0.1mmol的2-二环己基膦-2’,6’-二异丙氧基-1,1’-联苯依次加入到1.0mL丙酮中，得到混合物；
(2)在氮气氛围下，将步骤(1)中所得的混合物在62℃的反应温度下反应11小时，再从反应产物中收集出吡啶衍生物化合物53。
实施例54
(1)在氮气氛围下，将0.25mmol 4-吡啶季膦盐、0.1mmol 4-甲氧基碘苯、0.3mmol碳酸钾、0.12mmol的高氯酸银、0.005mmol醋酸钯、0.01mmol的2-二环己基膦-2’,6’-二异丙氧基-1,1’-联苯依次加入到1.0mL丙酮中，得到混合物；
(2)在氮气氛围下，将步骤(1)中所得的混合物在68℃的反应温度下反应13小时，再从反应产物中收集出吡啶衍生物化合物54。
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内所作的任何修改、等同替换和改进等，均应包含在本发明的保护范围之内。

Claims (7)

1.一种吡啶衍生物化合物，其特征在于，该化合物的化学结构式如下式(Ⅰ)所示：
Figure FDA0002475806610000011
式(Ⅰ)中，被R1取代的苯基为4-甲氧基苯基、3,5-二氟苯基、3-叔丁基苯基、3-溴苯基、2-氯苯基、2,6-二甲基苯基、萘基、苯并呋喃基、联苯基、4-甲酸甲酯苯基、4-三氟甲基苯基、4-硝基苯基、4-氰基苯基、4-乙酰基苯基、4-乙酰胺苯基、4-三甲基硅基苯基、苯并二氧五环基、3,5-二甲基异恶唑基、N-甲基吡唑基、N-苯基咔唑基、噻吩基、三异丙基硅基乙炔基、3,4-二氢萘基、苯甲酸香叶酯基、苯甲酸薄荷酯基、雌酚酮衍生物、布洛芬衍生物以及生育酚衍生物中的任意一种；
被R2取代的氮杂环基团为2-氟吡啶、2-氯吡啶、2-苯基吡啶、2,3-环己基吡啶、3-甲基吡啶、3-甲氧基吡啶、3-苯基吡啶、3-氟吡啶、3-甲酸甲酯基吡啶、3-氰基吡啶、N-甲基-7-氮杂吲哚、吡丙醚、比沙可啶、3-(1-二苯甲基氮杂环丁基-3-甲氧基甲基)吡啶、1-苯磺酰基-4-吡啶基哌嗪、(2-(4-甲氧基苯基)-4-(三氟甲基)吡啶、2-氯-5-乙基-4-(4-甲氧基苯基)嘧啶、2-(4-甲氧基苯基)吡嗪、5-(4-甲氧基苯基)-2,3-二甲基吡嗪、辛可尼丁、4-氟-4'-甲氧基-1,1'-联苯、4-甲酸甲酯-4'-甲氧基-1,1'-联苯以及4-三氟甲基-4'-甲氧基-1,1'-联苯)中的任意一种。
2.权利要求1所述的吡啶衍生物化合物的制备方法，其特征在于，该方法包括以下步骤：
(1)在惰性气体氛围下，将杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体依次加入到溶剂中，得到混合物，其中，所述杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体的摩尔比为2.5～25：1～10：3～30：1.2～12：0.5％～5％：1％～10％，所述碘化物与溶剂的摩尔体积比为0.1mmol：1mL；
(2)在惰性气体氛围下，将步骤(1)中得到的混合物在62～68℃温度下反应11～13小时，收集反应产物为吡啶衍生物化合物。
3.如权利要求2所述的吡啶衍生物化合物的制备方法，其特征在于，在步骤(1)中，所述杂环季膦盐为4-吡啶季膦盐、2-氟吡啶-4-季膦盐、2-氯吡啶-4-季膦盐、2-苯基吡啶-4-季膦盐、2,3-环己基吡啶-4-季膦盐、3-甲基吡啶-4-季膦盐、3-甲氧基吡啶-4-季膦盐、3-苯基吡啶-4-季膦盐、3-氟吡啶-4-季膦盐、3-甲酸甲酯基吡啶-4-季膦盐、3-氰基吡啶-4-季膦盐、N-甲基-7-氮杂吲哚-4-季膦盐、吡丙醚季膦盐、比沙可啶季膦盐、3-(1-二苯甲基氮杂环丁基-3-甲氧基甲基)吡啶季膦盐、1-苯磺酰基-4-吡啶基哌嗪季膦盐、4-三氟甲基吡啶-2-季膦盐、2-氯-5-乙基-4-嘧啶季膦盐、2-吡嗪季膦盐、2,3-二甲基吡嗪-5-季膦盐、辛可尼丁季膦盐、4-氟苯季膦盐、4-甲酸甲酯苯基季膦盐以及4-三氟甲基苯基季膦盐中的至少一种。
4.如权利要求2所述的吡啶衍生物化合物的制备方法，其特征在于，在步骤(1)中，所述碘化物为4-甲氧基碘苯、3,5-二氟碘苯、3-叔丁基碘苯、3-溴碘苯、2-氯碘苯、2,6-二甲基碘苯、碘化萘、碘代苯并呋喃、碘代联苯、4-甲酸甲酯碘苯、4-三氟甲基碘苯、4-硝基碘苯、4-氰基碘苯、4-乙酰基碘苯、4-乙酰胺碘苯、4-三甲基硅基碘苯、碘代苯并二氧五环、3,5-二甲基碘代异恶唑、N-甲基碘代吡唑、N-苯基碘代咔唑、碘代噻吩、三异丙基硅基碘代乙炔、3,4-二氢碘化萘、4-碘苯甲酸香叶酯、4-碘苯甲酸薄荷酯、碘代雌酚酮衍生物、碘代布洛芬衍生物以及碘代生育酚衍生物中的至少一种。
5.如权利要求2所述的吡啶衍生物化合物的制备方法，其特征在于，在步骤(1)中，所述碱为碳酸钾；所述添加剂为高氯酸银；所述钯催化剂为醋酸钯；
所述膦配体为2-二环己基膦-2’,6’-二异丙氧基-1,1’-联苯或者二苯基环己基膦；
所述溶剂为丙酮。
6.如权利要求2所述的吡啶衍生物化合物的制备方法，其特征在于，在步骤(1)中，所述杂环季膦盐、碘化物、碱、银添加剂、钯催化剂、磷配体的摩尔比为2.5：1：3：1.2：0.5％：1％。
7.如权利要求2所述的吡啶衍生物化合物的制备方法，其特征在于，所述惰性气体为氮气。
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