Issue 10, 2008
From the journal:

Organic & Biomolecular Chemistry

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  

* 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

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Article information

DOI
https://doi.org/10.1039/B719641E
Article type
Paper
Submitted
20 Dec 2007
Accepted
22 Feb 2008
First published
25 Mar 2008

Org. Biomol. Chem., 2008,6, 1763-1772

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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

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