First Diels-Alder Reaction of Pyrazolyl Imines under Microwave Irradiation

Angel Díaz-Ortiz; JoséR. Carrillo; María J. Gómez-Escalonilla; Antonio de la Hoz; Andrés Moreno; Pilar Prieto

doi:10.1055/s-1998-1881

Synlett 1998; 1998(10): 1069-1070
DOI: 10.1055/s-1998-1881

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First Diels-Alder Reaction of Pyrazolyl Imines under Microwave Irradiation

Angel Díaz-Ortiz^* , José R. Carrillo, María J. Gómez-Escalonilla, Antonio de la Hoz, Andrés Moreno, Pilar Prieto

^*Facultad de Química, Universidad de Castilla-La Mancha, 13071-Ciudad Real, Spain

Abstract

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Microwave irradiation in solvent-free conditions induces pyrazolyl 2-azadienes to undergo Diels-Alder cycloadditions with nitroalkenes within 5-10 min to give good yields of pyrazolo[3,4-b]pyridines. This is the first example of a [4 + 2] cycloaddition of a 2-azadiene involving a pryazole ring. By classical heating, these reactions do not occur or afford only traces of the products.

2-azadiene - pyrazolyl derivative - Diels-Alder - nitroalkene - microwave

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