2004
DOI: 10.1590/s0100-40422004000100019
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Síntese de enaminonas

Abstract: Recebido em 18/9/02; aceito em 13/6/03 SYNTHESIS OF ENAMINONES. The general term "enaminone" is applied to any compound bearing the conjugated system N-C=C-C=O. Enaminones are typical capto-dative ethylenes, showing particular properties due to π-electron delocalization. Their reactivity can be predicted by structural patterns of substitution, conformation and configuration, making them versatile synthetic building blocks. In this review, a variety of methods for the synthesis of enaminones is described. The m… Show more

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Cited by 31 publications
(20 citation statements)
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References 68 publications
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“…The most direct route for the synthesis of enamino compounds is the condensation of a primary amine and a REVIEW Jul-Aug 2004 463 1,3-diketone or 3-ketoester [1,2,21]. The reaction is usually facile when uncrowded primary amines are involved.…”
Section: Preparation Of Enaminoketonesmentioning
confidence: 99%
See 1 more Smart Citation
“…The most direct route for the synthesis of enamino compounds is the condensation of a primary amine and a REVIEW Jul-Aug 2004 463 1,3-diketone or 3-ketoester [1,2,21]. The reaction is usually facile when uncrowded primary amines are involved.…”
Section: Preparation Of Enaminoketonesmentioning
confidence: 99%
“…Enaminones of all types exist predominantly in the carbonyl form A and are stabilized by the contribution of the zwitterionic form (C - Figure 3) which can be solvated by water preventing hydrolysis of the formed enaminone. When the enaminone is formed, it is stabilized by resonance, blocking the formation of other products [26].The conjugate addition of benzyl carbamate 14 to α,β-unsaturated ketones 15 catalysed by Cu (II) -Cu(OTf) 2 complexes, leads to β-aminoketones 16 bearing a benzyloxy carbonyl moiety (Figure 10), which can easily undergo further conversions using well-established protective group chemistry [27].Synthesis of Enaminones Through Ring-opening of Isoxazoles.Isoxazoles are generally considered as useful synthons in organic synthesis, and 5-alkyl or 5-aryl isoxazole in the presence of iron dichloride, as catalyst, undergo reductive cleavage to enaminoketones [21,28]. Reduction of isoxazoles gave enaminoketones as the only products.…”
mentioning
confidence: 99%
“…Among these heterocycles, the pyrrolizidines, indolizidines and pyrroloazepines are important classes of alkaloids from the medicinal chemistry and chemical ecology point of views. 1 We disclosure herein our results concerning the formal aza-[3+2] and formal aza-[3+3] cycloaddition reactions of cyclic enaminones, including a chiral one, with maleic anhydride and N-aryl-maleimides, wherein pyrrolizidines, indolizidines and pyrroloazepines could be selectively obtained.…”
Section: Introductionmentioning
confidence: 99%
“…For this reason, enaminones have found a wide application in the synthesis of various heterocycles, dyes and drugs. 22,[30][31][32] Specifically, we have described the synthesis of N- [1-aryl(alkyl)-3-oxo-4,4,4-trifluoro(chloro) 29 The purpose of this paper is to report the complete results of the reactions of 4-alkoxy-4-alkyl(aryl/heteroaryl)-1,1,1-trifluoroalk-3-en-2-ones (1a-j) with 1,3-phenylenediamine to obtain a wide series of ten examples of trifluoroacetyl substituted 1,3-phenylene-bis-enamines (2a-j) and also to investigate the chemical behavior of alkyl, aryl and heteroaryl-substituted enamino intermediates (2) for their application in the simultaneous regioselective synthesis of new 2,8-or 4,8-bis(trifluoromethyl)-2,10-bis-alkyl(aryl)-1,7-phenanthrolines (3) and the respective 4-(trifluoromethyl)-7-aminoquinolines (4) under similar reaction conditions as described previously.…”
Section: Introductionmentioning
confidence: 99%