Abstract
Diazo coupling of 3,4‐dimethoxyfuran with aryl diazonium ions3,4‐Dimethoxyfuran (1) easily reacts with aryl diazonium chloride in aqueous pyridine in an expected 1, 4‐addition reaction. From the isolable primary addition product pyridine is displaced by alcohols, phenols or thiols to yield 4‐alkoxy‐ or 4‐phenoxy‐ or 4‐thiophenoxy‐derivatives of 2,3‐dimethoxy‐2‐buten‐4‐olide (3). Attempts to convert them into azo compounds by a base catalysed 1, 6‐elimination reaction failed. Oxidation of 3a and 3c with DDQ results in the formation of the mono p‐nitrophenylhydrazone of 3, 4‐dimethoxymaleic acid anhydride. On the other hand, the thiophenoxy compound 3g is smoothly converted by MnO2 into the authentic furan‐2‐azobenzene derivative 5.
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