Synthesis of Polysubstituted 3-Methylisoquinolines through the 6?-Electron Cyclization/Elimination of 1-Azatrienes derived from 1,1-Dimethylhydrazine

Artículo

Autoría

Vargas Vargas, Didier Farley ; LARGHI, ENRIQUE LEANDRO ; KAUFMAN, TEODORO SAUL

Fecha

2018

Editorial y Lugar de Edición

Wiley VCH Verlag

Revista

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, vol. 2018 (pp. 5605-5614) Wiley VCH Verlag

Resumen Información suministrada por el agente en SIGEVA

A convenient one pot microwave-assisted 6?-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The... A convenient one pot microwave-assisted 6?-electron cyclization/aromatization approach toward 3-methylisoquinolines is reported. The starting 1-azatriene derivatives were prepared in situ by reaction of 2-propenylbenzaldehydes with 1,1-dimethylhydrazine, which exhibited superior performance when compared with other hydrazine derivatives. Minor amounts of the related 3,4-dihydro isoquinolines were formed concomitantly with the isoquinolines, and a mechanism for their generation was proposed. The reaction conditions were optimized, and its scope and limitations were explored. In general, the transformation proceeded in moderate to good yields.

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Palabras Clave

ELECTRON CYCLIZATIONBENZOTRIFLUORIDE3-METHYLISOQUINOLINENITROGEN HETEROCYCLESHYDRAZONES

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http://hdl.handle.net/11336/87135