Journal
TETRAHEDRON
Volume 69, Issue 39, Pages 8429-8438Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2013.07.055
Keywords
Pyrazoles; Heterocycles; Microwaves; P38 MAPK; JNK1
Categories
Funding
- EPSRC [EP/I037229/1]
- Saudi Cultural Bureau
- BBSRC [BB/D524140/1]
- SPARC
- ESRC [RES-356-25-0024]
- RM Phillips Trust
- Biotechnology and Biological Sciences Research Council [BB/D524140/1] Funding Source: researchfish
- Economic and Social Research Council [ES/G037205/1] Funding Source: researchfish
- Engineering and Physical Sciences Research Council [EP/I037229/1] Funding Source: researchfish
- BBSRC [BB/D524140/1] Funding Source: UKRI
- EPSRC [EP/I037229/1] Funding Source: UKRI
- ESRC [ES/G037205/1] Funding Source: UKRI
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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.
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