Jump to main content
Jump to site search
Publishing
Advanced

Issue 10, 2008
Previous Article Next Article

Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles†

Yosu Vara,a   Eneko Aldaba,b   Ana Arrieta,a   José L. Pizarro,c   María I. Arriortuac  and  Fernando P. Cossío*a  
Author affiliations

* Corresponding authors

a Kimika Fakultatea, Kimika Organika I Saila, Universidad del País Vasco – Euskal Herriko Unibertsitatea, Manuel de Lardizabal Etorbidea 3, San Sebastián-Donostia, Spain
E-mail: fp.cossio@ehu.es
Fax: +34 943 015270
Tel: +34 943 015442

b Ikerchem Ltd, Tolosa Etorbidea 72, San Sebastián-Donostia, Spain

c Zientzia eta Teknologia Fakultatea, Mineralogia eta Petrologia Saila, Universidad del País Vasco – Euskal Herriko Unibertsitatea, Bilbao, Spain

Abstract

The scope and regioselectivity of the Bischler (or Bischler–Möhlau) reaction between aromatic amines and α-bromoketones has been studied by computational and experimental techniques. It has been found that in many cases the reaction yields are improved under microwave irradiation and working in the absence of solvent. When di- and trisubstituted amines are used as substrates the regioselectivity of the reaction is different to that obtained with the corresponding primary anilines. The reaction between benzene-1,2-diamine and α-bromoacetophenones under the same conditions yields 2-substituted quinoxalines instead of indoles. Finally, when pyridin-2-amines and pyrimidine-2-amines are allowed to react with the corresponding α-bromoacetophenones, the corresponding imidazo[1,2-a]pyridines and imidazo[1,2-a]pyrimidines are obtained, respectively.

Graphical abstract: Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles

Back to tab navigation
Download options Please wait...

Supplementary files

Article information

https://doi.org/10.1039/B719641E
Submitted
20 Dec 2007
Accepted
22 Feb 2008
First published
25 Mar 2008
Org. Biomol. Chem., 2008,6, 1763-1772
Article type
Paper
Permissions
Request permissions

Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles

Y. Vara, E. Aldaba, A. Arrieta, J. L. Pizarro, M. I. Arriortua and F. P. Cossío, Org. Biomol. Chem., 2008, 6, 1763
DOI: 10.1039/B719641E

If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using Copyright Clearance Center. Go to our Instructions for using Copyright Clearance Center page for details.

Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.
  • For reproduction of material from PCCP:
    Reproduced from Ref. XX with permission from the PCCP Owner Societies.
  • For reproduction of material from PPS:
    Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.
  • For reproduction of material from all other RSC journals and books:
    Reproduced from Ref. XX with permission from The Royal Society of Chemistry.

If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

In all cases the Ref. XX is the XXth reference in the list of references.

If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

Reproduced material should be attributed as follows:

  • For reproduction of material from NJC:
    [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC
  • For reproduction of material from PCCP:
    [Original citation] - Reproduced by permission of the PCCP Owner Societies
  • For reproduction of material from PPS:
    [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
  • For reproduction of material from all other RSC journals:
    [Original citation] - Reproduced by permission of The Royal Society of Chemistry

If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Social activity

Search articles by author

Spotlight

Advertisements