Regiocontrolled synthesis of 3- and 5-aminopyrazoles, pyrazolo[3,4-d]pyrimidines, pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]quinolinones as MAPK inhibitors
Regiocontrolled synthesis of 3- and 5-aminopyrazoles, pyrazolo[3,4-d]pyrimidines, pyrazolo[3,4-b]pyridines and pyrazolo[3,4-b]quinolinones as MAPK inhibitors
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DOI：
10.1016/j.tet.2013.07.055
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发表时间：
2013-09-30
期刊：
影响因子：
2.1
通讯作者：
Davis, Terence
中科院分区：
文献类型：
--
作者：
Bagley, Mark C.;Baashen, Mohammed;Davis, Terence
肼和3-甲氧基丙烯腈、乙氧基亚甲基丙二腈或乙酰乙酸乙酯的微波辐射提供了快速获得3-或5-取代的吡唑的方法，该方法具有优异的产率和完全的区域控制，该方法可以通过选择条件从一种区域异构体转换到另一种区域异构体。随后的反应，通过微波辅助水解和与甲酰胺的环化缩合，与醛和酮的Hantzsch型三组分反应，或通过与2-硝基苯甲醛的环化缩合，分别提供促分裂原活化蛋白激酶抑制剂的吡唑并[3，4-d]嘧啶、吡唑并[3，4-B]吡啶或吡唑并[3，4-B]喹啉-4-酮骨架。(C)2013爱思唯尔有限公司保留所有权利。
Microwave irradiation of a hydrazine and 3-methoxyacrylonitrile, ethoxymethylenemalononitrile or ethyl acetoacetate provides rapid access to 3- or 5-substituted pyrazoles in excellent yield and with total regiocontrol in a process that can be switched from one regioisomer to the other by choice of conditions. Subsequent reaction, either by microwave-assisted hydrolysis and cyclocondensation with formamide, Hantzsch-type three-component reaction with an aldehyde and ketone, or by cyclocondensation with 2-nitrobenzaldehyde, provides the pyrazolo[3,4-d]pyrimidine, pyrazolo[3,4-b]pyridine or pyrazolo[3,4-b]quinolin-4-one framework, respectively, of inhibitors of mitogen-activated protein kinases. (C) 2013 Elsevier Ltd. All rights reserved.