7-氨基-6-芳基偶氮-5-羟基吡唑[1,5-a]并嘧啶-3-甲酸乙酯的合成
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摘要
以氰乙酸乙酯和原甲酸三乙酯为原料,经过缩合、肼解、关环、重氮化及偶合等反应合成了13个新型的嘌呤类似物7-氨基-6-芳基偶氮-5-羟基吡唑[1,5-a]并嘧啶-3-甲酸乙酯(5a-5m)。通过IR、~1H NMR、MS和元素分析确定了所得化合物的结构。
In the basis of ethyl cyanoacetate and triethyl orthoformate,13 new purine analogues were synthesized by condensation,nitrile hydrolysis,cyclization,diazotization and coupling reaction. They were 7-amino-6-arylazo-5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate derivatives( 5a-5m). The structures of target compounds were characterized by IR,and ~1H-NMR,MS and elemental analysis.
In the basis of ethyl cyanoacetate and triethyl orthoformate,13 new purine analogues were synthesized by condensation,nitrile hydrolysis,cyclization,diazotization and coupling reaction. They were 7-amino-6-arylazo-5-hydroxypyrazolo[1,5-a]pyrimidine-3-carboxylate derivatives( 5a-5m). The structures of target compounds were characterized by IR,and ~1H-NMR,MS and elemental analysis.
引文
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[4]Matthias D,Karen M,Rob D V,et al.Design,synthesis,and antiviral evaluation of purine-β-lactam and purineaminopropanol hybrids[J].J Med Chem,2012,55(11):5637-5 641.
[5]Chaikuad A,Brady R L.Conservation of structure and activity in plasmodium purine nucleoside phosphorylases[J].BMC Structural Biology,2009,9(1):1-18.
[6]Pierre R,Dominique S,Christian M,et al.Cyclic nucleotide phosphodiesterase type 4 inhibitors:Evaluation of pyrazolo[1,5-a]-1,3,5-triazine ring system as an adenine bioisostere[J].Eur J Med Chem,2008,43(4):816-829.
[7]Hwu J R,Lin S Y,Tsay S C,et al.Coumarin-purine ribofuranoside conjugates as new agents against hepatitis C virus[J].J Med Chem,2011,54(7):2 114-2 126.
[8]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):1 140-1 142.
[9]Nouri K,Yazdanparast R.Effects of 3-hydrogen kwadaphnin on intracellular purine nucleotide contents and their link to K562 cell death[J].Food Chem,2011,128(1):81-86.
[10]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.
[11]Yang B,Lu Y,Chen J C,et al.The synthesis of 5-amino-4-arylazo-3-methyl-1H-pyrazoles and 5-aryl-3-methylpyrazole[3,4-e][1,2,3,4]tetrazines[J].Dyes and Pigments,2009,83(2):144-147.
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[14]钟世华,王春凤,宋青霞,等.2-氰基-3-取代丙烯酸(2-乙氧基乙基)酯的合成及除草活性[J].有机化学,2014,34(11):2 324-2 330.
[15]蒋华江,孙日勇,蔡继平.3(5)-氨基吡唑-4-甲酸乙酯的合成研究[J].化工时代,2005,19(3):12-13.