Tris(pentafluorophenyl)borane-Catalyzed Three-Component Reaction for the Synthesis of 1,8-Dioxodecahydroacridines under Solvent-Free Conditions

Srivari Chandrasekhar; Yaragorla Srinivasa Rao; Lella Sreelakshmi; Bodugam Mahipal; Chada Raji Reddy

doi:10.1055/s-2008-1067039

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Synthesis 2008(11): 1737-1740
DOI: 10.1055/s-2008-1067039

PAPER

Tris(pentafluorophenyl)borane-Catalyzed Three-Component Reaction for the Synthesis of 1,8-Dioxodecahydroacridines under Solvent-Free Conditions

Srivari Chandrasekhar*, Yaragorla Srinivasa Rao, Lella Sreelakshmi, Bodugam Mahipal, Chada Raji Reddy
Organic Division I, Indian Institute of Chemical Technology, Hyderabad 500007, India
Fax: +91(40)27160512; e-Mail: srivaric@iict.res.in;

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Publication History

Received 8 January 2008
Publication Date:
29 April 2008 (online)

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Abstract

A mild and efficient method for the synthesis of 1,8-dioxodecahydroacridines has been developed. The synthesis proceeds via a three-component reaction of a 1,3-dione, an aldehyde and an amine, under solvent-free conditions, catalyzed by tris(pentafluorophenyl)borane [B(C₆F₅)₃]. The mildness of the catalyst was demonstrated by studying the reaction of 1,3-cyclohexanedione with various aldehydes and amines which gave the 1,8-dioxodecahydroacridines in high yields.

Key words

Hantzsch reaction - acridinediones - tris(pentafluorophenyl)borane - three-component reaction - Lewis acid

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