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

Gilbert Revial; Ivan Jabin; Sethy Lim; Michel Pfau

doi:10.1021/jo0110597

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

J Org Chem. 2002 Apr 5;67(7):2252-6. doi: 10.1021/jo0110597.

Authors

Gilbert Revial¹, Ivan Jabin, Sethy Lim, Michel Pfau

Affiliation

¹ Laboratoire de Chimie Organique, CNRS (ESA 7084), ESPCI, 10 rue Vauquelin, 75231 Paris Cedex 05, France.

PMID: 11925236
DOI: 10.1021/jo0110597

Abstract

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 POCl(3), 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.

MeSH terms

Bufotenin / chemical synthesis*
Catalysis
Chemistry, Organic / methods
Chromatography, Thin Layer
Cyclization
Imines / chemistry
Indoleacetic Acids / chemical synthesis*
Indoleacetic Acids / chemistry
Indoles / chemical synthesis*
Indoles / chemistry
Melatonin / chemical synthesis*
Molecular Structure
Picrates / chemistry
Serotonin / chemical synthesis*

Substances

Imines
Indoleacetic Acids
Indoles
Picrates
methyl-1-benzyl-5-methoxy-1H-indole-3-acetate
Bufotenin
Serotonin
Melatonin