Bromination of dimethyl 1-substituted indole-2,3-dicarboxylates
Bromination of dimethyl 1-substituted indole-2,3-dicarboxylates
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1-取代吲哚-2,3-二甲酸二甲酯的溴化
DOI：
10.3987/com-06-10796
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发表时间：
2006
期刊：
影响因子：
0.6
通讯作者：
Y. Aoki
中科院分区：
文献类型：
--
作者：
Y. Miki*;Hideaki Umemoto;Maiko Nakamura;H. Hibino;Noriko Ohkita;Akiko Kato;Y. Aoki
5-溴吲哚-2，3-二甲酸二甲酯在Lewis酸存在下与氢溴化吡啶或溴反应，得到唯一产物5-溴吲哚-2，3-二甲酸二甲酯。以类似的方式，1-苄基和L-苯磺酰基-吲哚-2，3-二羧酸二甲酯提供了相应的5-溴吲哚和6-溴吲哚衍生物的混合物。然而，甲基l-trifluoromethanesulfonylindole-2，3-dicarboxylate以甲基6-bromo-1-trifluoromethanesulfonylindole-2，3-dicarboxylate为主要产品。
Treatment of dimethyl indole-2,3-dicarboxylate with pyridinium hydrobromide perbromide or bromine in the presence of Lewis acid gave dimethyl 5-bromoindole-2,3-dicarboxylate as the sole product. In a similar manner, dimethyl 1-benzyl- and l-benzenesulfonyl-indole-2,3-dicarboxylates provided a mixture of the corresponding 5-bromoindole and 6-bromoindole derivatives. However, methyl l-trifluoromethanesulfonylindole-2,3-dicarboxylate gave methyl 6-bromo-1-trifluoromethanesulfonylindole-2,3-dicarboxylate as a major product.