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Synthesis 2011(12): 1930-1935  
DOI: 10.1055/s-0030-1260048
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© Georg Thieme Verlag Stuttgart ˙ New York

Efficient Organocatalytic Dual Activation Strategy for Preparing the Versatile Synthons (2E)-1-(Het)Aryl/styryl-3-(dimethylamino)prop-2-en-1-ones and α-(E)-[(Dimethylamino)methylene]cycloalkanones

Sachin Bindal, Dinesh Kumar, Damodara N. Kommi, Sonam Bhatiya, Asit K. Chakraborti*
National Institute of Pharmaceutical Education and Research (NIPER), Sector 67, S. A. S. Nagar, Punjab 160062, India
Fax: +91(172)2214692; e-Mail: akchakraborti@niper.ac.in;
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Publication History

Received 30 March 2011
Publication Date:
17 May 2011 (online)

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Abstract

A novel organocatalytic dual activation strategy is reported for an efficient synthesis of the versatile synthons (2E)-1-aryl/heteroaryl/styryl-3-(dimethylamino)prop-2-en-1-ones and α-(E)-[(dimethylamino)methylene]cycloalkanones. 2-Guanidinoacetic acid (10 mol%) serves as an ambifunctional organocatalyst for the reaction of various aryl/heteroaryl/styryl methyl ketones and cyclic ketones having an α-methylene moiety with N,N-dimethyl­formamide dimethyl acetal at 100 ˚C for 1-3 hours under solvent-free conditions to afford the corresponding (2E)-3-(dimethylamino)prop-2-en-1-ones in 72-95% yields.

Key words

2-guanidinoacetic acid - organocatalyst - dual activation - 3-(dimethylamino)propenones - aryl methyl ketone - N,N-di­methylformamide dimethyl acetal