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Digitale Medien

Cyclization Studies with N-Mannich bases of 2-substituted indoles (1989)

Burger, Ulrich ; Bringhen, Alain O.

New York, NY : Wiley-Blackwell

Helvetica Chimica Acta 72 (1989), S. 93-100

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Details

ISSN: 0018-019X

Schlagwort(e): Chemistry ; Organic Chemistry

Quelle: Wiley InterScience Backfile Collection 1832-2000

Thema: Chemie und Pharmazie

Notizen: The synthesis of the indoles 7, 15, 16 with a 3-methoxyphenyl group, attached via an α-side chain of 1,2,or 3 CH2 units, is reported. These compounds, after appropriate protection at C(3), were transformed into the N-[(dimethylamino)methyl]indoles 22, 23, and 24, respectively. When treated with AcCl, these N-Mannich bases gave, in two cases, stable N-(chloromethyl)indoles 25 and 26. In the presence of SnCl4, ring closure occurred via electrophilic attack of 1-methylideneindolium ions on the methoxyphenyl group. Formation of seven-membered rings (→ 27, 28) and eight-membered rings (→ 29) was found to be a favorable process. Cyclization to six-membered rings did not occur within this series.

Materialart: Digitale Medien

URL: http://dx.doi.org/10.1002/hlca.19890720112

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