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vol.56 issue1PHOTOACTIVE POLYACRYLONITRILE FIBERS COATED BY NANO-SIZED TITANIUM DIOXIDE: SYNTHESIS, CHARACTERIZATION, THERMAL INVESTIGATIONMODIFICATION OF BORON DOPED DIAMOND ELECTRODES WITH GLUCOSE OXIDASE, CHARACTERIZATION BY ELECTROCHEMICAL TECHNIQUES author indexsubject indexarticles search
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Journal of the Chilean Chemical Society

On-line version ISSN 0717-9707

Abstract

IMANZADEH, GHOLAMHASSAN; AGHAALIZADEH, TOORAN; ZAMANLOO, MOHAMMADREZA  and  MANSOORI, YAGOUB. SOLVENT-FREE MICROWAVE MICHAEL ADDITION OF ISATIN AND ANILINE SCHIFF BASE OF ISATIN TO α,β-UNSATURATED ESTERS. J. Chil. Chem. Soc. [online]. 2011, vol.56, n.1, pp.616-620. ISSN 0717-9707.  http://dx.doi.org/10.4067/S0717-97072011000100021.

The rapid, simple, microwave-assisted Michael addition of isatin and aniline Schiff base of isatin to a wide variety of alkyl and aryl acrylates in the presence of, tetrabutylammonium bromide (TBAB) and 1,4-diazabicyclo[2.2.2]octane (DABCO), under solvent-free conditions, is presented. Under these conditions the addition of isatin to some of alkyl and aryl acrylates afford both related Baylis-Hillman adducts as minor products and the corresponding Michael adducts as major products. Addition of isatin to ethyl acrylate leads to produce Baylis-Hillman/Michael adduct in good yield. This system dose not work on Michael acceptors of methyl acrylate and methyl methacrylate.

Keywords : Aza-Michael addition; Microwave; Isatin; Isatin Schiff base; α,β-unsaturated Esters.

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