Reaction with Enamines

With an attempt to develop a synthetic method for pyrrolo[2,3-fr]indoles having a C - C bond at the 3a-position like 160, TsCl (or MsCl) is added to a mixture of 1-hydroxymelatonin (161), 1-(4-morpholinyl)cyclohexene (162), and Et3NinCHCl3. An unusual reaction has occurred, though it's based on the nature of 1-hydroxyindole skeletons: products are Nb-acetyl-3-hydroxy-5-methoxy-2-(4-morpholinyl)-3ff-indole-3-ethanamine (163a, 37%), 2-[3-(2-acetylaminoethyl)-5-methoxy-3ff-indol-3-yl]cyclohexanone (164, 4%), and melatonin (64, 8%) (Scheme 21) [40]. The same reaction of 1-hydroxy-Nb-methoxycarbonylindole-3-ethanamine (52) provides 3-hydroxy-Nb-methoxy-carbonyl-2-(4-morpholinyl)-3ff-indole-3-ethanamine (163b, 44%) and Nb-methoxycarbonyl-6-tosyloxyindole-3-ethanamine (165, 11%).

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