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

Bagley, Mark C., Baashen, Mohammed, Paddock, Victoria L., Kipling, David Glyn and Davis, Terence ORCID: https://orcid.org/0000-0003-2780-0262 2013. 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. Tetrahedron 69 (39) , pp. 8429-8438. 10.1016/j.tet.2013.07.055

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Abstract

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.

Item Type:	Article
Date Type:	Publication
Status:	Published
Schools:	Medicine
Subjects:	R Medicine > R Medicine (General) R Medicine > RZ Other systems of medicine
Uncontrolled Keywords:	Heterocycles; JNK1; Microwaves; P38 MAPK; Pyrazoles
Publisher:	Elsevier
ISSN:	0040-4020
Last Modified:	14 Dec 2022 02:18
URI:	https://orca.cardiff.ac.uk/id/eprint/75383

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