Journal of Organic Chemistry 2002-04-05

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

文献索引：J. Org. Chem. 67 , 2252, (2002)

摘要

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.

结构式	名称/CAS号	分子式	全部文献
	1,4-环己二酮单乙二醇缩酮 CAS:4746-97-8	C₈H₁₂O₃
	蟾蜍色胺 CAS:487-93-4	C₁₂H₁₆N₂O

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[Aldrichimica Acta 12 , 40, (1979)]

[Tetrahedron 50 , 731, (1994)]

[Synlett , 81, (1994)]

[Synth. Commun. 24 , 799, (1994)]

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.

摘要

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