CN1105106C - 萘酚衍生物及其制备方法 - Google Patents

萘酚衍生物及其制备方法 Download PDF

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CN1105106C
CN1105106C CN97191988A CN97191988A CN1105106C CN 1105106 C CN1105106 C CN 1105106C CN 97191988 A CN97191988 A CN 97191988A CN 97191988 A CN97191988 A CN 97191988A CN 1105106 C CN1105106 C CN 1105106C
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上野隆三
北山雅也
南宪次
若森浩之
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Ueno Seiyaku Oyo Kenkyujo KK
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Abstract

本发明涉及新的2-羟基萘-3，6-二羧酸衍生物。该化合物用作染料、颜料、光敏材料等的原料。

Description

萘酚衍生物及其制备方法
                        技术领域
本发明涉及可被用作合成染料，颜料，光敏材料等的原料的新的萘酚衍生物，及其制备方法。
                        发明背景
萘酚衍生物是形成共轭多烯系统，并具有电子吸附带，适用于作合成原料的最经济的稠合芳香化合物。因此，到目前为止，它已被用作各种特性化合物，特别是作为染料，颜料，光敏材料等的原料。
在这些萘酚衍生物中，其中取代基位于2-羟基萘的3-或6-位的2-羟基-3-苯基氨羰基萘，2-羟基-6-苯基氨羰基萘，以及在这些苯基上连接有烷基或烷氧基的化合物是已知的。
但是，在2-羟基萘的3-和6-位都有取代基的萘衍生物中，目前仅已知2-羟基-3，6-二羟基羰基萘。
本发明的目的便是提供用作合成原料的新的3，6-二取代-2-羟基萘衍生物，特别是2-羟基-3，6-二羟基羰基萘衍生物及其制备方法。
                      发明的公开
本发明涉及通式(I)表示的萘酚衍生物及其制备方法，
Figure C9719198800041
[其中Y为-(CONH)n-X或-COR，
Y′为-(CONH)n-X′或-COR′，
X和X′可以相同或不同，表示吡啶基，噻唑基，苯并噻唑基或咪唑基，各基团可任意地被取代。
R和R′可以相同或不同，表示羟基，具有1到6个碳原子可任意为支链的烷氧基，卤原子，苄氧基，苯氧基或苯甲酰甲氧基，
R2为氢原子，碱金属，具有1到6个碳原子可任意为支链的烷基、具有1到6个碳原子的酰基或苯基亚烷基，
Z为选自氢原子，卤原子，硝基，亚硝基或氨基的一种或多种基团(Z可以在萘环的任何一个环上取代)，以及
n为1或2的整数，条件是Y和Y′不能分别同时为-COR和-COR′]。
具体地说本发明涉及通式(IV)和(IV′)表示的萘酚衍生物：
Figure C9719198800051
其中通式(I)的取代基Y和Y′中的一个为-(CONH)n-X，而另一个为-(CONH)n-X或-COR[其中X，n和R定义如上]。
本发明的萘酚衍生物(I)为新的萘酚衍生物。
本发明的萘酚衍生物(IV)和(IV′)为新化合物，其中任意取代的吡啶基，噻唑基，苯并噻唑基或咪唑基通过氨羰基或-CONH-CO-NH-基连接在2-羟基萘的3-位和/或6-位。在3-位和6-位通过氨羰基或-CONHCONH-基连接的这些残基可以相同或不同。在3-位和6-位的连接基团(氨羰基和-CONHCONH-基)也可以相同或不同。
本发明萘酚衍生物3-位和6-位之一可为羟羰基，具有1到6个碳原子任意为支链的烷氧羰基，苄氧羰基，苯氧羰基或苯甲酰甲氧羰基。2-位羟基的氢原子可被碱金属原子，具有1到6个碳原子任意为支链的烷基，具有1到6个碳原子的酰基或苯基取代的亚烷基取代。萘环上可连接一种或多种选自卤原子，硝基，亚硝基和氨基的基团。
当X为取代的吡啶基，噻唑基，苯并噻唑基或咪唑基时，所述取代基的例子为：烷基，烷氧基，卤代烷基，苯氧基，烷氧羰基，硝基，卤原子，羟基，氨基，苯甲酰氨基，二烷氨基磺酰基和氰基。烷基可是任意为支链的具有1到6个碳原子的饱和或不饱和烷基。优选的烷基包括甲基，乙基，丙基，异丙基，丁基或叔丁基。烷氧基可为具有1到6个碳原子的饱和或不饱和任意为支链的烷氧基。优选的烷氧基包括甲氧基和乙氧基。卤原子的例子为氟，氯，溴和碘。取代基的数量为1到5，取代基可以相同或不同。
本发明的上述萘酚衍生物(IV)或(IV′)可通过使通式(II)表示的萘酚衍生物：[其中取代基R4和R4′中的一个为羟基或卤原子，而另一个为羟基，卤原子，具有1到6个碳原子可任选为支链的烷氧基，苄氧基，苯氧基或苯甲酰甲氧基；R5为氢原子或羟基保护基，Z的定义如上]，与通式(III)表示的杂环化合物：
         H2N-R3-X                 (III)[其中R3为单键或-CONH-，条件是X的定义如上]缩合而制备。
式(II)中，R5为氢原子，碱金属原子或羟基保护基。羟基保护基表示，在其他位置上引入取代基所进行的反应期间，暂时与羟基键合以保护该羟基并在所需反应结束后容易通过碱或酸水解等处理再生为羟基的基团，该保护基的例子为，具有1到6个碳原子任意为支链的烷基，苄基，乙酰基，丙酮基，四氢呋喃基，三甲基甲硅烷基等。
通过使用氰酸盐法，使相应的杂环化合物与氰酸反应形成脲基，可得到其中R3为-CONH-的式(III)化合物中的苯基脲衍生物。
更具体地说，如下列反应方案所示(VI)：[其中X定义如上]，例如，将杂环化合物溶于乙酸水溶液中，在15℃  30分钟内滴加氰酸钾水溶液进去，加完后加热至30℃，使混合物反应30分钟，过滤沉淀出的结晶，并用水洗涤而得到目的化合物。
例如将2-羟基-3，6-二羟基羰基萘和杂环化合物溶于二甲苯，在90至100℃下，在该溶液中滴加三氯化磷，然后该溶液加热至140℃，并反应3小时，可完成化合物(II)和(III)的反应。反应完成后，在反应混合物中加入水，中和该混合物，过滤沉淀出的结晶，将滤纸上的结晶用有机溶剂如二甲苯洗涤，得到化合物(IV)或(IV′)。
为了在R2中引入氢原子以外的取代基，例如，可以使其中3-位和6-位被保护的相应的2-羟基-3，6-二羟基羰基萘的3，6-衍生物与卤化物反应，所述卤化物具有要引入的取代基，例如苄基氯，碘乙烷等，该反应在合适的碱性物质如碳酸钾的存在下进行。
为了将卤原子等作为取代基Z引入萘环，可将溶于氯仿等的卤分子如溴加入其中的萘环相应位置未被取代的萘化合物溶液中。为了引入亚硝基，可将亚硝酸钠水溶液加入其中的萘环所需位置未被取代的萘化合物的溶液中。
                     附图的简要说明
图1为实施例1所得化合物的红外吸收谱。
图2为实施例2所得化合物的红外吸收谱。
图3为实施例3所得化合物的红外吸收谱。
图4为实施例4所得化合物的红外吸收谱。
图5为实施例5所得化合物的红外吸收谱。
图6为实施例6所得化合物的红外吸收谱。
                        实施例
实施例1
2-羟基-3，6-二(2′-吡啶基氨羰基)萘的合成
Figure C9719198800071
将2-羟基-3，6-二羟基羰基萘(14.3g)和2-氨基吡啶(13.6g)溶于N-甲基-2-吡咯烷酮(120g)和乙酸乙酯(150g)中。在该溶液中加入二环己基碳化二亚胺(30.9g)，使该混合物在室温下反应15小时。滤除不溶物后，将滤液浓缩至原重量的一半并加入二甘醇二甲醚(30.6g)，将所得混合物加热至170℃。2小时后，将反应混合物冷却至室温，滤除不溶物。浓缩滤液，在浓缩液中加入乙酸乙酯(200g)，将所得混合物进行超声处理，沉淀出结晶状产物，然后将其过滤及干燥，得到黄白色粉末状2-羟基-3，6-二(2′-吡啶基氨羰基)萘(15.7g)(熔点：311.2℃)。
红外吸收谱(KBr法)如图1所示。
实施例2
2-羟基-3，6-二(噻唑-2′-基氨羰基)萘的合成
Figure C9719198800081
将2-氨基噻唑(6.3g)溶于N-甲基-2-吡咯烷酮(50.0g)和甲苯(30.0g)的混合物中，将该溶液加热至60℃。在该溶液中加入2-羟基-3，6-二氯羰基萘(5.6g)溶于N-甲基-2-吡咯烷酮(120.0g)形成的溶液，并将该混合物加热至80℃。约24小时后，浓缩反应混合物，在浓缩液中加入水(470g)。将沉淀出的结晶滤出，用甲醇洗涤，干燥，得到皮肤色粉末状2-羟基-3，6-二(噻唑-2′-基氨羰基)萘(1.7g)(熔点：286.6℃)。
红外吸收谱(KBr法)如图2所示。
实施例3
2-羟基-3，6-二(苯并噻唑-2′-基氨羰基)萘的合成
除使用2-氨基苯并噻唑(9.4g)代替2-氨基噻唑外，按与实施例2所述相同的方法得到皮肤色粉末状2-羟基-3，6-二(苯并噻唑-2′-基氨羰基)萘(3.2g)(熔点：364.1℃).
红外吸收谱(KBr法)如图3所示。
实施例4
2-羟基-3，6-二(4′，5′-二氰基咪唑-2′-基氨羰基)萘的合成
Figure C9719198800091
除用2-氨基-4，5-二氰基咪唑(8.3g)代替2-氨基噻唑外，按与实施例2所述相同的方法得到皮肤色粉末状2-羟基-3，6-二(4′，5′-二氰基咪唑-2′-基氨羰基)萘(3.5g)(熔点：256.8℃).
红外吸收谱(KBr法)如图4所示。
实施例5
2-羟基-3-甲氧基羰基-6-(苯并噻唑-2′-基氨羰基)萘的合成
除用2-羟基-3-甲氧羰基-6-氯羰基萘(2.6g)代替2-羟基-3，6-二氯羰基萘外，按与实施例3所述相同的方法得到浅黄色粉末状2-羟基-3-甲氧羰基-6-(苯并噻唑-2′-基氨羰基)萘(3.5g)(分解温度：375.3℃)。
红外吸收谱(KBr法)如图5所示。
实施例6
2-羟基-6-甲氧羰基-3-(4′，5′-二氰基咪唑-2′-基氨羰基)萘的合成
除用2-羟基-6-甲氧羰基-3-氯羰基萘(5.3g)代替2-羟基-3，6-二氯羰基萘外，按与实施例3所述相同的方法得到浅棕色粉末状2-羟基-6-甲氧羰基-3-(4′，5′-二氰基咪唑-2′-基氨羰基)萘(5.0g)(分解温度：323.1℃)。
红外吸收谱(KBr法)如图6所示。

Claims (2)

1.通式(I)表示的萘酚衍生物：
Figure C9719198800021
其中Y为-(CONH)n-X或-COR，
Y′为-(CONH)n-X′或-COR′，
X和X′可以相同或不同，表示吡啶基、噻唑基、苯并噻唑基或咪唑基，各基团可任选地被选自烷基、烷氧基、卤代烷基、苯氧基、烷氧羰基、硝基、卤原子、羟基、氨基、苯甲酰氨基、二烷氨基磺酰基和氰基的取代基所取代，其中所述烷基可任选地为支链的具有1到6个碳原子的饱和或不饱和烷基，所述烷氧基可为具有1到6个碳原子的饱和或不饱和任选为支链的烷氧基，
R和R′可以相同或不同，表示羟基，具有1到6个碳原子任选为支链的烷氧基、卤原子、苄氧基、苯氧基或苯甲酰甲氧基，
R2为氢原子、碱金属、具有1到6个碳原子任选为支链的烷基、具有1到6个碳原子的酰基或苯基亚烷基，
Z为选自氢原子、卤原子、硝基、亚硝基或氨基的一种或多种基团，Z可以在萘环的任何一个环上取代，以及
n为1或2的整数，条件是Y和Y′不能分别同时为-COR和-COR′。
2.一种制备权利要求1萘酚衍生物的方法，其中包括通式(II)表示的萘酚衍生物：与通式(III)表示的杂环化合物缩合：
           H2N-R3-X                  (III)其中R3为单键或-CONH-，条件是X的定义如权利要求1；其中式(II)中的取代基R4和R4′的一个为羟基或卤原子，而另一个为羟基、卤原子、具有1到6个碳原子可任选为支链的烷氧基、苄氧基、苯氧基或苯甲酰甲氧基；R5为氢原子或羟基保护基；Z的定义如权利要求1。
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