Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2005, Issue 11, Pages 2354-2367Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.200400845
Keywords
chemoselective Biginelli-type reaction; cycloalkanones; spiro heterotricyclic scaffolds
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The classical Biginelli reaction is considerably extended by use of cycloalkanones instead of 1,3-dicarbonyl compounds. Use of TMSC1 as a Lewis acid allowed one-pot chemoseleclive multicomponent Biginelli reactions between cycloalkanones, urea or thiourea, and aldehydes. Under similar reaction conditions, thiourea exhibited different behavior to urea, and aliphatic aldehydes showed lower reactivity than aromatic aldehydes. A possible mechanism to account for the reaction is proposed. (c) Wiley-VCH Verlag GmbH & Co.
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