Regioselective synthesis of novel substituted indazole-5,6-diamine derivatives |
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Authors: | Laurent Gavara Emmanuelle Saugues Fabrice Anizon Pascale Moreau |
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Institution: | a Clermont Université, Université Blaise Pascal, Laboratoire SEESIB, BP 10448, F-63000 Clermont-Ferrand, France b CNRS, UMR 6504, SEESIB, F-63177 Aubière, France |
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Abstract: | The synthesis of a series of novel indazole-5,6-diamine derivatives is described. This indazole ring system was incorporated in an octahydropyrrolo3,4-b]phenazine scaffold and was diversely and regioselectively substituted on the nitrogen atoms at the 5- and 10-positions. Thus, the nitrogen atom at the 5-position was found to be more reactive toward electrophiles than the one at the 10-position. This difference of reactivity could be attributed to the electronic effect of the pyrazole moiety. Moreover, an unexpected tetrahydropyran protecting group migration was observed from the N-1 atom to the C-11 position of the octahydropyrrolo3,4-b]phenazine scaffold. |
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Keywords: | Indazole Phenazine Regioselective alkylation |
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