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Note | Regular issue | Vol 65, No. 1, 2005, pp.133-142
Published online, 9th November, 2004
DOI: 10.3987/COM-04-10112
Chemoselective Multicomponent Condensation of 1,3-Cyclohexanedione, Urea or Thiourea with Aldehydes: One-Pot Synthesis of Two Families of Fused Heterobicyclic and Spiro-fused Heterobicyclic Aliphatic Rings

Yulin Zhu, Yuanjiang Pan,* and Shenlin Huang

*Department of Chemistry, Zhejiang University (YuQuan Campus), Hangzhou, 310027, China

Abstract

One-pot chemoselective condensation of 1,3-cyclohexanedione, urea or thiourea with aldehydes has been performed by using TMSCl as a Lewis acid in DMF/MeCN. This extended Biginelli-type reaction afforded two families of fused heterobicyclic and spiro-fused heterobicyclic compounds in excellent yields. para-Substituted benzaldehydes exhibited different chemical behaviors to ortho- or meta-substituted benzaldehydes and aliphatic aldehydes. The possible mechanism was discussed to account for experimental results.