A benzyne type reaction of 1‐bromo‐3,4‐dimethoxybenzene (V) with 3,4‐dihydro‐6,7‐methylenedioxy‐I(2H)naphthalenone (VI) gave the tetralone derivative VII, which was converted into the amine IX via the oxime VIII. A Mannich reaction of IX afforded the benzo[c]phen‐anthridine II which was then transformed into oxynitidine (I) and nitidine (IV).
A benzyne reaction of 1 -(2-bromo-4.5-methylenedioxybenzyl) -1.2.3.4-tetrahydro-7-hydroxy-6-methoxy-2-methylisoquinoline (4) with sodium amide in liquid ammonia afforded amurine (1 0) and domesticine (1 3). The same reaction was carried out in the presence of potassium ferricyanide to give amurine (1 0) and 1.2.3.4-tetrahydro-7-hydroxy-I -(3-hydroxybenzyl)-6-methoxy-2-methylisoquinoline (6).
Synthesis of 1‐(2‐tetrahydrol'uryl)‐5‐fluorouracil [Ftorafur] (1) which is well known as an antitumor agent from 5‐fluorouracil (2) with 2‐alkoxytetrahydrofurans (4) is described. Among these reactions, the best yield was obtained by using 2‐t‐butoxytetrahydrofuran (4h).
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