Tetrahedron p. 6821 - 6826 (1992)
Update date:2022-08-04
Topics:
Gonsalves, Antonio M. d'A. Rocha
Melo, Teresa M. V. D. Pinho e
Benzyne has been generated from benzenediazonium-2-carboxylate in the presence of several 1,2,4-triazines 1 and isoquinolines 2 have been isolated in moderate yield. 1-Aminobenzotriazole was also used as the source of benzyne and isoquinolines were again isolated in moderate yield from these reactions. 4-Methylbenzyne, which was generated from 5-methylanthranilic acid, reacted unselectively with the triazines to give mixtures of 6- and 7-methylisoquinolines 3 and 4.On the other hand reactions of 3-methylbenzyne with the triazines 1d and 1e proceeded with high regioselectivity, giving only the 5-methylisoquinoline 5a and the 8-methylisoquinoline 6b, respectively.
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