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

Bindal, Sachin ; Kumar, Dinesh ; Kommi, Damodara ; Bhatiya, Sonam ; Chakraborti, Asit K. (2011) 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 Synthesis, 2011 (12). pp. 1930-1935. ISSN 0039-7881

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Official URL: https://www.thieme-connect.de/DOI/DOI?10.1055/s-00...

Related URL: http://dx.doi.org/10.1055/s-0030-1260048

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.

Item Type:Article
Source:Copyright of this article belongs to Thieme Publishing.
Keywords:2-Guanidinoacetic Acid; Organocatalyst; Dual Activation; 3-(Dimethylamino)Propenones; Aryl Methyl Ketone; N,N-Di­methylformamide Dimethyl Acetal
ID Code:100390
Deposited On:20 Jan 2017 08:51
Last Modified:20 Jan 2017 08:51

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