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Aromatization of 1,6,7,7a-Tetrahydro-2H-indol-2-ones by a Novel Process. Preparation of Key-Intermediate Methyl 1-Benzyl-5-methoxy-1H-indole-3-acetate and the Syntheses of Serotonin, Melatonin, and Bufotenin

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Laboratoire de Chimie Organique, CNRS (ESA 7084), ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France, and URCOM, Université du Havre, Faculté des Sciences et Techniques, 25 rue Philippe Lebon BP 540, 76058 Le Havre Cedex, France
Cite this: J. Org. Chem. 2002, 67, 7, 2252–2256
Publication Date (Web):March 7, 2002
https://doi.org/10.1021/jo0110597
Copyright © 2002 American Chemical Society
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Abstract

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Imine 7 of 1,4-cyclohexanedione mono-ethylene ketal 6 was reacted with maleic anhydride, affording the cyclized adduct 8. Methyl esterification of 8, accompanied by transacetalization, led to the dihydrooxindole derivative 10. Aromatization of 10 was then accomplished with POCl3, leading directly to the key-intermediate title compound 11 in 74% yield from ketone 6. Serotonin, melatonin, and bufotenin were then obtained by standard reactions.

†

 Laboratoire de Chimie Organique, CNRS (ESA 7084).

‡

 URCOM, Université du Havre.

*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

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1H and 13C NMR spectra of compounds 1, 2, 3, 7, 8, 9, 10, 10a, 10b, 11, 12, 13, 14, 15, 16, 17; 1H spectra of the dipicrate of 3, picrate of 17. This material is available free of charge via the Internet at http://pubs.acs.org.

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  18. Yu-Yun Wang, Chinpiao Chen. Synthesis of a deuterium-labelled standard of bufotenine (5-HO-DMT). Journal of Labelled Compounds and Radiopharmaceuticals 2007, 50 (14) , 1262-1265. https://doi.org/10.1002/jlcr.1459
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  20. T.O.G. Costa, R.A.V. Morales, J.P. Brito, M. Gordo, A.C. Pinto, C. Bloch. Occurrence of bufotenin in the Osteocephalus genus (Anura: Hylidae). Toxicon 2005, 46 (4) , 371-375. https://doi.org/10.1016/j.toxicon.2005.02.006
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  22. Valentine G. Nenajdenko, Eugene P. Zakurdaev, Eugene V. Prusov, Elizabeth S. Balenkova. Convenient synthesis of melatonin analogues: 2- and 3-substituted -N-acetylindolylalkylamines. Tetrahedron 2004, 60 (51) , 11719-11724. https://doi.org/10.1016/j.tet.2004.10.006
  23. Stéphane Le Gac, Nicolas Monnier-Benoit, Lionel Doumampouom Metoul, Samuel Petit, Ivan Jabin. Stereoselective synthesis of new classes of atropisomeric compounds through a tandem Michael reaction–azacyclization process. Part 2. Tetrahedron: Asymmetry 2004, 15 (1) , 139-145. https://doi.org/10.1016/j.tetasy.2003.10.025
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