Volume 29, Issue 40
Heterocyclic Compounds
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ChemInform Abstract: Lewis Acid Catalyzed Reaction of 2-Isopropenylaniline with Ketones: Improved Synthesis of 2,2,4-Trisubstituted 1,2-Dihydroquinolines.

J. P. EDWARDS

J. P. EDWARDS

Dep. Med. Chem., Ligand Pharm., Inc., San Diego, CA 92121, USA

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J. D. RINGGENBERG

J. D. RINGGENBERG

Dep. Med. Chem., Ligand Pharm., Inc., San Diego, CA 92121, USA

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T. K. JONES

T. K. JONES

Dep. Med. Chem., Ligand Pharm., Inc., San Diego, CA 92121, USA

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First published: 19 June 2010

Abstract

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ChemInform Abstract

BF3×OEt2-Mediated condensation of 2-isopropenylaniline (I) with ketones affords title compounds (III). Sterically hindered ketones such as (Ic) and (Id) give low or no yields. The reaction proceeds via initial formation of an imine which can be isolated in the case of benzophenone.

chemical structure image

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