1,4-Dioxane-2,3-diol → 4-Hydroxyacridine

Beteiligte Stoffe

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Charts A1-A3 summarise the routes used in the synthesis of a series of pyrido[3,2-d]pyrimidin-4-ol derivatives. The preparation of the derivatives of [1,7]naphthyridin-8-ol is described in Charts B1-B2. Compound B1 was prepared following the literature method2 for the synthesis of a similar compound. The synthesis of the pyrido[2,3-d]pyridazin-8-ol itself and derivatives C1 and C2 followed the method previously described3 by Brzezinski and coworkers. Further derivatives in this series were prepared following the routes summarised in Charts C1-C4. Charts D1-D2 show the routes to a series of [1,6]naphthyridin-8-ol derivatives. The synthesis of compound D1 used the method4 of Blanco and coworkers. Other members in this series have been prepared following the routes shown in Charts D1-D2. Chart E1 describes the route to a series of pyrido[3,4-b]pyrazin-5-ol derivatives. Condensation of 1,2,3-triaminopyridine with 2,3-dihydroxy-1,4-dioxan gave pyrido[3,4-b]pyrazin-5-ol (E1), the parent compound in this series; the same reaction employing 2,3,4-triaminopyridine as starting material (Chart F1) gave pyrido[3,4-b]pyrazin-8-ol (F1). Further derivatives in the pyrido[3,4-b]pyrazin-5-ol and pyrido[3,4-b]pyrazin-8-ol classes were prepared using the routes shown in Charts E1 and F1. Charts G1-G2 show the routes employed in the synthesis of a range of [1,5]naphthyridin-4,8-diol and [1,5]naphthyridin-8-ol derivatives. The synthesis of compound G1, the precursor to the parent compound, [1,5]naphthyridin-4,8-diol, followed the route described5 by Brown and Dewar. Pyrido[4,3-d]pyrimidin-8-ol (H1) was prepared4 following the route shown in Chart H1, employing 4,5-pyrimidinedicarboxylic acid as starting material. Further derivatives in this class were prepared using routes as shown in Charts H1 and H2.

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