新型2-甲基-5-羟基-7-氨基-吡唑[1,5-a]并嘧啶衍生物的合成
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摘要
以3-甲基-5-氨基-吡唑和氰乙酸乙酯为原料,合成了2-甲基-5-羟基-7-氨基-吡唑[1,5-a]并嘧啶(2);2与芳胺的重氮盐溶液反应,合成了7个新型的2-甲基-5-羟基-6-芳基偶氮-7-亚氨基-吡唑[1,5-a]并嘧啶衍生物,收率87%~93%,其结构经~1H NMR,IR和ESI-MS表征。
2-Methyl-5-hydroxy-7-amino-pyrazole[1,5-a]pyrimidine( 2) was obtained by the reaction of 3-methyl-5-amino-pyrazole with ethyl cyanoacetate. Seven novel 2-methyl-5-hydroxy-6-arylazo-7-imino-pyrazole[1,5-a]-pyrimidine derivatives( 3a ~ 3f) were synthesized by the reaction of 2 with diazonium salt solution of arylamines. The yield of 3a ~ 3f were 87% ~ 93%. The structures were characterized by~1 H NMR,IR and ESI-MS.
2-Methyl-5-hydroxy-7-amino-pyrazole[1,5-a]pyrimidine( 2) was obtained by the reaction of 3-methyl-5-amino-pyrazole with ethyl cyanoacetate. Seven novel 2-methyl-5-hydroxy-6-arylazo-7-imino-pyrazole[1,5-a]-pyrimidine derivatives( 3a ~ 3f) were synthesized by the reaction of 2 with diazonium salt solution of arylamines. The yield of 3a ~ 3f were 87% ~ 93%. The structures were characterized by~1 H NMR,IR and ESI-MS.
引文
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[4]Cohen S,megherbi M,Jordheim L P,et al.Simultaneous analysis of eight nucleoside triphosphates in cell lines by liquid chromatography coupled with tandem mass spectrometry[J].Chromatogr B,2009,877(30):3831-3840.
[5]杨娜,郝琳,鲁源,等.5-亚氨基-7-氧代-6-芳基偶氮-1,3,4-噻二唑[3,2-a]并嘧啶衍生物的绿色合成[J].化学试剂,2012,34(12):1139-1141.
[6]郝琳,刘俊宝,陈建平,等.2-甲基-5,7-二氧代-1,3,4-噻二唑[3,2-a]并嘧啶及其衍生物的合成[J].化学试剂,2013,35(12):1140-1142.
[7]宋振丽,郝琳,鲁源,等.3-氨基-5H-5-芳基吡唑[3,4-e]并-1,2,3,4-四嗪衍生物的合成[J].化学试剂,2013,35(2):176-177.
[8]Liu J B,Lu Y,Chen J C,et al.Synthesis of some novel arylazo disperse dyes derived from 5-amino-tetrazolo[1,5-a]pyrimidin-7-ol as coupling component and investigation of their absorption spectra[J].J Heterocyclic Chem,2013,50(6):1441-1445.
[9]鲁源,杨慧,布仁,等.2-羟基-3-苯偶氮吡唑[5,1-c]苯并-1,2,4-三嗪衍生物的合成[J].化学试剂,2004,26(4):239-240.
[10]王淑月,王洪亮,钮敏.生物电子等排原理在新药设计中的应用[J].河北工业科技,2003,20(3):50-53.
[11]Hans J K,Reinhard T,Hermann J R.Synthesis von5-aminopyrazolo[1,5-a]pyrimidin-7(4H)-onen[J].Arch Pharm,1985,318(2):135-142.
[12]Basaif S A,Hassan M A,Gobouri A A.Al Cl3-Catalyzed diazocoupling of 1-(aryl/hetaryl)-3-phenyl-1Hpyrazol-2-in-5-ones in aqueous medium:Synthesis of hetaryl-azopyrazolones and their application as disperse dyes[J].Dyes and Pigments,2007,72(3):387-391.
[13]Khalil A K,Hassan M A,Mohamed M M,et al.Metal salt-catalyzed diazocoupling of 3-substituted-1H-pyrazol-2-in-5-ones in aqueous medium[J].Dyes and Pigments,2005,66(3):241-245.