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Cyclization Studies with N-Mannich bases of 2-substituted indoles

✍ Scribed by Ulrich Burger; Alain O. Bringhen

Book ID: 102856984
Publisher: John Wiley and Sons
Year: 1989
Tongue: German
Weight: 513 KB
Volume: 72
Category: Article
ISSN: 0018-019X
DOI: 10.1002/hlca.19890720112

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✦ Synopsis

The synthesis of the indoles 7,15,16 with a 3-methoxyphenyl group, attached via an a-side chain of 1,2, or 3 CH, 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 AcCI, these N-Munnich bases gave, in two cases, stable N-(chloromethy1)indoles 25 and 26. In the presence of SnCI,, 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.

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