en
Scientific article
English

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

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

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.

Funding
  • 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
Main files (1)
Article (Published version)
accessLevelRestricted
Identifiers
ISSN of the journal0018-019X
135views
0downloads

Technical informations

Creation07/08/2021 3:57:00 PM
First validation07/08/2021 3:57:00 PM
Update time03/16/2023 12:52:31 AM
Status update03/16/2023 12:52:31 AM
Last indexation01/17/2024 1:40:08 PM
All rights reserved by Archive ouverte UNIGE and the University of GenevaunigeBlack