TiCl4-promoted condensation of methyl acetoacetate, isobutyraldehyde, and indole: a theoretical and experimental study-Reference-Cited by-同舟云学术

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

Published:2015 Issue:14 Volume:17 Page:8964-8972
ISSN:1463-9076
Container-title:Physical Chemistry Chemical Physics
language:en
Short-container-title:Phys. Chem. Chem. Phys.

Author:

Renzetti Andrea¹²³⁴,Marrone Alessandro⁵⁶⁷⁸,Gérard Stéphane⁹¹⁰¹¹¹²¹³,Sapi Janos⁹¹⁰¹¹¹²¹³,Nakazawa Hiroshi¹²³⁴,Re Nazzareno⁵⁶⁷⁸,Fontana Antonella⁵⁶⁷⁸

Affiliation:

1. Department of Chemistry

2. Osaka City University

3. 558-8585 Osaka

4. Japan

5. Dipartimento di Farmacia

6. Università “G. d'Annunzio” di Chieti-Pescara

7. I-66100 Chieti

8. Italy

9. Institut de Chimie Moléculaire de Reims

10. UMR CNRS 7312

11. Université de Reims Champagne-Ardenne

12. Faculté de Pharmacie

13. F-51096 Reims

Abstract

A combined DFT and experimental study of the title reaction points to a three-step mechanism: (1) titanium enolate formation, (2) Knoevenagel condensation of enolate and aldehyde, and (3) Michael addition of indole.

Publisher

Royal Society of Chemistry (RSC)

Subject

Physical and Theoretical Chemistry,General Physics and Astronomy

Link

http://pubs.rsc.org/en/content/articlepdf/2015/CP/C4CP05412A

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