Synthesis of acronycine isosters

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Abstract
The synthesis of the two key intermediates 6,8-dihydroxy-10-methylbenzo[b][1,8]naphthyridin-5(10H)-one (4b) and 6,8-dihydroxy-5H-[1]benzopyrano[2,3-b]pyridin-5-one (4d) for the synthesis of acronycine isosteres is described. The condensation of (4b) with 3-chloro-3-methylbut-1-yne afforded three isomers (5), (6), and (7), from which it was possible to distinguish between the angular isomer (5) and the linear isomer (6) with the aid of 13C n.m.r. spectroscopy. The condensation of (4d) with 3-chloro-3-methylbut-1-yne yielded only one product (8). The action of dimethyl sulphate on 6-hydroxy-3,3-dimethyl-3H-pyrano[2′,3′ : 7,8]chromeno[2,3-b]pyridin-7-one (8) as well as on 6,8-dimethoxy-5H-[1]benzopyrano[2,3-b]pyridin-5-one (3b) is also reported.

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