FISCHER INDOLE SYNTHESIS OF 3-BENZYL-1<i>H</i>-INDOLE VIA CONDUCTIVE AND DIELECTRIC HEATING

Authors

  • Jesco Panther Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf
  • Julian Rechmann Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf
  • Thomas J. J. Müller Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf

DOI:

https://doi.org/10.1007/3380

Keywords:

indole, acid catalysis, condensation, Fischer indole synthesis, Heck isomerization, microwave-assisted reactions, one-pot reactions, thermal reactions

Abstract

As a part of designing one-pot synthesis conditions for a combination of Heck isomerization and Fischer indolization (HIFI sequence), a model reaction was studied using 3-phenylpropanal and phenylhydrazine to furnish 3-benzyl-1H-indole under conductive and dielectric heating. While Amberlyst® 15 as an acidic catalyst or T3P® (propylphosphonic acid cyclic anhydride) as a condensation agent gave high yields of 3-benzyl-1H-indole under both conductive and dielectric heating, these agents were not compatible with the conditions of the initial Heck isomerization. However, the catalyst-free thermal process for the indolization step proceeded with good yields in conjunction with the preceding Heck isomerization in a one-pot process under dielectric heating in N-methylpyrrolidone as a solvent.

 

Author Biography

Thomas J. J. Müller, Institute of Organic and Macromolecular Chemistry, Heinrich Heine University Düsseldorf, Universitätsstrasse 1, D-40225 Düsseldorf

Institut für Organische Chemie und Makromolekulare Chemie

Institute director and chair of organic chemistry

Downloads

Published

2016-12-02

Issue

Vol. 52 No. 11 (2016): Non-classical methods of activation in chemistry of heterocyclic compounds

Section

Original Papers