Scientific article

Cyclization Studies with N-Mannich Bases of 2-Substituted Indoles

Published inHelvetica Chimica Acta, vol. 72, no. 1, p. 93-100
Publication date1989

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.

  • Swiss National Science Foundation - 2005-5.376
Citation (ISO format)
BURGER, Ulrich, BRINGHEN, Alain Olivier. Cyclization Studies with <i>N-Mannich</i> Bases of 2-Substituted Indoles. In: Helvetica Chimica Acta, 1989, vol. 72, n° 1, p. 93–100. doi: 10.1002/hlca.19890720112
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Article (Published version)
ISSN of the journal0018-019X

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