Jump to main content
Jump to site search

Issue 14, 2015
Previous Article Next Article

TiCl4-promoted condensation of methyl acetoacetate, isobutyraldehyde, and indole: a theoretical and experimental study

Author affiliations

Abstract

The mechanism of the TiCl4-promoted condensation of methyl acetoacetate, isobutyraldehyde, and indole was studied by a combination of theoretical and experimental techniques. The energy profile of plausible reaction paths was evaluated by DFT calculations, and various reaction intermediates were isolated or observed in solution by NMR spectroscopy. Theoretical and experimental results indicate that the reaction proceeds in three steps, all promoted by titanium: (1) formation of the enolate ion of methyl acetoacetate, (2) Knoevenagel condensation of the enolate ion and aldehyde, and (3) Michael addition of indole to the Knoevenagel adduct. The study sheds light on the role of titanium in the reaction, providing a mechanistic model for analogous reactions.

Graphical abstract: TiCl4-promoted condensation of methyl acetoacetate, isobutyraldehyde, and indole: a theoretical and experimental study

Back to tab navigation

Supplementary files

Publication details

The article was received on 20 Nov 2014, accepted on 20 Feb 2015 and first published on 09 Mar 2015


Article type: Paper
DOI: 10.1039/C4CP05412A
Author version
available:
Download author version (PDF)
Phys. Chem. Chem. Phys., 2015,17, 8964-8972

  •   Request permissions

    TiCl4-promoted condensation of methyl acetoacetate, isobutyraldehyde, and indole: a theoretical and experimental study

    A. Renzetti, A. Marrone, S. Gérard, J. Sapi, H. Nakazawa, N. Re and A. Fontana, Phys. Chem. Chem. Phys., 2015, 17, 8964
    DOI: 10.1039/C4CP05412A

Search articles by author

Spotlight

Advertisements