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Updated: Feb 13, 2026

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SeCl2-Mediated Approach Toward Indole-Containing Polysubstituted Selenophenes.

Guilherme M Martins1, Davi F Back1, Teodoro S Kaufman2

  • 1Departamento de Química , Universidade Federal de Santa Maria , Santa Maria , RS 97105-900 , Brazil.

The Journal of Organic Chemistry
|March 3, 2018
PubMed
Summary
This summary is machine-generated.

This study introduces a new method using selenium tetrachloride (SeCl2) for synthesizing 3-selenophen-3-yl-1H-indoles. The efficient process involves a unique rearrangement and cyclization at room temperature.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry
  • Heterocyclic Chemistry

Background:

  • Indole derivatives are crucial in medicinal chemistry.
  • Developing efficient synthetic routes for functionalized indoles is an ongoing challenge.
  • Selenium-containing heterocycles offer unique chemical properties and biological activities.

Purpose of the Study:

  • To develop a novel and efficient method for synthesizing 3-selenophen-3-yl-1H-indoles.
  • To explore a new chalcogenative cyclization strategy using selenium tetrachloride.
  • To investigate the mechanism of the proposed selenirenium-induced rearrangement.

Main Methods:

  • Reaction of substituted propargyl indoles with selenium tetrachloride (SeCl2).
  • Electrophilic addition to the alkyne followed by a 1,2-indolyl shift.
  • Intramolecular cyclization to form the 3-selenophen-3-yl-1H-indole core.

Main Results:

  • A novel SeCl2-mediated chalcogenative cyclization strategy was established.
  • The reaction proceeds via a selenirenium intermediate and a 1,2-indolyl shift.
  • The synthesis is efficient, selective, and tolerant of various functional groups, occurring at room temperature.

Conclusions:

  • The described method provides a facile route to 3-selenophen-3-yl-1H-indoles.
  • The reaction mechanism involves unprecedented selenirenium-induced rearrangement.
  • This strategy offers a valuable tool for constructing selenium-containing indole derivatives.