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Article Dans Une Revue Tetrahedron Année : 2011

Regioselective synthesis of novel substituted indazole-5,6-diamine derivatives

Résumé

The synthesis of a series of novel indazole-5,6-diamine derivatives is described. This indazole ring system was incorporated in an octahydropyrrolo[3,4-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 octahydropyrrolo[3,4-b]phenazine scaffold.
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Dates et versions

hal-00566169 , version 1 (15-02-2011)

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  • HAL Id : hal-00566169 , version 1

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Laurent Gavara, Emmanuelle Saugues, Fabrice Anizon, Pascale Moreau. Regioselective synthesis of novel substituted indazole-5,6-diamine derivatives. Tetrahedron, 2011, 67, pp.1633-1639. ⟨hal-00566169⟩
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