Palladium-catalyzed reactions in the synthesis of 3- and 4-substituted indoles. 4

Journal Article · Fri Aug 18 04:00:00 EDT 1989 · Journal of Organic Chemistry; (USA)

DOI:https://doi.org/10.1021/jo00278a029· OSTI ID:7196823

Hegedus, L S; Sestrick, M R; Michaelson, E T; Harrington, P J ^[1]

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1. Colorado State Univ., Fort Collins (USA)

4-Bromo-1-tosylindole (1) was converted to tricyclic indole enone 11, a potential intermediate in the synthesis of tetracyclic ergot alkaloids, by a series of palladium-catalyzed processes. Attempts to construct the ergot D ring by the hetero-Diels-Alder reaction of enone 11 and 1-azabutadiene 12 produced not the expected (4 + 2) adduct 13 but the benz(cd)indoline derivative 14 resulting from attack of the aza diene at the indole 2-position. The thermodynamic stability of the naphthol nucleus makes enone 11 generally susceptible to attack at the indole 2-position, as evidenced by the attack of hydride and methyl cuprate nucleophiles at this portion forming indolines 16 and 17, respectively.

• OSTI ID: 7196823
• Journal Information: Journal of Organic Chemistry; (USA), Journal Name: Journal of Organic Chemistry; (USA) Vol. 54:17; ISSN JOCEA; ISSN 0022-3263
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
AROMATICS
AZAARENES
AZOLES
CATALYSTS
DATA
DATA ANALYSIS
ELEMENTS
EXPERIMENTAL DATA
HETEROCYCLIC COMPOUNDS
INDOLES
INFORMATION
MEASURING INSTRUMENTS
MEASURING METHODS
METALS
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC NITROGEN COMPOUNDS
PALLADIUM
PLATINUM METALS
PYRROLES
SYNTHESIS
TRANSITION ELEMENTS