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Issue 10, 2008
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Regiochemistry of the microwave-assisted reaction between aromatic amines and α-bromoketones to yield substituted 1H-indoles

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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


Submitted
20 Dec 2007
Accepted
22 Feb 2008
First published
25 Mar 2008

Org. Biomol. Chem., 2008,6, 1763-1772
Article type
Paper

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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