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Synthesis 2000; 2000(8): 1117-1120
DOI: 10.1055/s-2000-6322
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The Superacid Induced Condensation of Quinolinecarboxaldehydes with Arenes

Douglas A. Klumpp* , Andre Jones, Siufu Lau, Sarah de Leon, Manuel Garza
  • *Department of Chemistry, California State Polytechnic University, 3801 West Temple Avenue, Pomona, California 91768, USA; Fax +1 (9 09) 8 69 43 96; E-mail: daklumpp@csupomona.edu
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Publication Date:
31 December 2000 (online)

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A variety of quinolinecarboxaldehydes have been reacted with arenes in the Brönsted superacid, CF3SO3H (triflic acid) to give condensation products in good to excellent yields (52-99%). The quinolinecarboxaldehydes are significantly more reactive than 2-naphthalenecarboxaldehyde. It is proposed that the increased reactivity is due to the formation of dicationic, electrophilic intermediates.

heterocycles - aldehydes - electrophilic aromatic substitutions - quinolines

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