Zhang Yan
2012
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Chemical Reagents
Abstract
2-Formyl(acetyl)-3-methylindole derivatives are important intermediates for the synthesis of fulgide photochromic dyes.3-Methylindoles were first N-alkylated to form 1-methyl or methoxyethyl compounds,then one formyl was introduced via Vilsmeier-Haack reaction.Two intermediates were prepared by this strategy.The total yields are 55% and 35% respectively.The trial to acetylated of 2-position of indoles did not afford desired products.ZnCl2 was used as Lewis acid,3-methylindoles could react with acetyl chloride in 2-position of indoles to form 2-acetyl-3-formyl indoles.The reactions are mild without protection and deprotection.A series of 2-acetyl-3-methyl indloes were prepared,their yields are 34%~89%.Four of these compounds were not reported in the literature.The structures were confirmed by 1HNMR,13CNMR,MS and element analysis.