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Synthesis of new 1H-indazoles through Diels-Alder transformations of 4-styrylpyrazoles under microwave irradiation conditions

AuthorsSilva, V. L. M.; Silva, A. M. S.; Pinto, Diana C. G. A.; Elguero, José ; Cavaleiro, José A. S.
Issue Date2009
PublisherJohn Wiley & Sons
CitationEuropean Journal of Organic Chemistry: 4468- 4479 (2009)
AbstractMicrowave irradiation under solvent-free conditions induces 1-acetyl-4-styrylpyrazoles to undergo Diels-Alder cycloaddition reactions with N-methyl- or N-phenylmaleimide to give tetrahydroindazoles in good yields and with high selectivities, With conventional heating, these reactions either do not occur or afford only traces of the cycloadducts. These cycloadducts were then converted into the corresponding 1Hindazoles by dehydrogenation with DDQ in dry 1,2,4-trichlorobenzene under microwave irradiation or classical heating conditions, The structures of all new derivatives and the stereochemistries of the cycloadducts were assigned by NMR spectroscopy. © 2009 Wiley-VCH Verlag GmbH & Co. KGaA.
Publisher version (URL)http://dx.doi.org/10.1002/ejoc.200900513
Identifiersdoi: 10.1002/ejoc.200900513
issn: 1434-193X
e-issn: 1099-0690
Appears in Collections:(IQM) Artículos
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