TiCl4/t-BuNH2-promoted hydroamination/annulation of δ-keto-acetylenes:: Synthesis of novel pyrrolo[1,2-a]indol-2-carbaldehydes

被引:54
作者
Abbiati, Giorgio [1 ]
Casoni, Alessandro [1 ]
Canevari, Valentina [1 ]
Nava, Donatella [1 ]
Rossi, Elisabetta [1 ]
机构
[1] Univ Milan, Fac Farm, Ist Chim Organ Alessandro Marchesini, I-20133 Milan, Italy
关键词
D O I
10.1021/ol061872u
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] An original TiCl4/t-BuNH2-mediated hydroamination/annulation domino reaction of delta-keto-acetylenes is described. The synthesis of pyrrolo[ 1,2-a] indole-2-carbaldehydes, starting from 2-carbonyl-1-propargyl-1H-indoles runs under mild reaction conditions. A conceivable mechanism is also discussed. TiCl4 has proved to be an effective multiactivity reagent: catalyst/Lewis acid/water scavenger. Some unpublished 2-carbonyl-1-propargyl- 1H-indoles are prepared by means of Suzuki- and Negishi-type reactions.
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页码:4839 / 4842
页数:4
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