Journal
TETRAHEDRON
Volume 67, Issue 5, Pages 936-942Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.12.003
Keywords
4,7-Disubstituted-tetrahydro-5-azaindoles; Diastereoselective Pictet-Spengler reaction; 2-(Aryl)-2-(1H-pyrrol-2-yl)ethanamines; 4,7-Disubstituted-5-azaindoles
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Funding
- MOHE in Yemen
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Pictet-Spengler condensation of 2-(aryl)-2-(1H-pyrrol-2-yl)ethanamines using conventional acid catalysts like TMSCl or TFA resulted in the formation of substituted 5-azaindoles involving a tandem one pot four steps reaction sequence. By contrast use of glacial acetic acid furnished the targeted tetrahydro-5-azaindoles in diastereoselective manner. These were readily dehydrogenated to 5-azaindoles. (C) 2010 Elsevier Ltd. All rights reserved.
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