Synthesis and Reactivity of β-Amino α,β -Unsaturated Ketones and Esters Using K-10 Montmorillonite

Braibante, Mara Elisa Fortes; Braibante, Hugo S.; Missio, Lauri J.; Andricopulo, Adriano D.

doi:10.1055/s-1994-25595

Cited by 97 publications

(42 citation statements)

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“…The yields of these compounds were 70-97%, an improvement when compared to the previously described procedure without microwave radiation. 11 The stereochemistry of compounds 1 and 2 is Z, as shown by the intramolecular hydrogen bonding in the 1 H NMR spectra that contain a typical N-H chemical shifts (8.45-12.47 ppm).…”

Section: Resultsmentioning

confidence: 99%

“…For compounds 4a,e and f, a mixture of E/Z isomers was observed based in the 1 H NMR spectra which showed N-H chemical shifts (9.04-10.04 ppm for E and 5.02-5.90 ppm for Z configuration) different from those observed for 1 and 2 (see Table 1). 11 For the preparation of the β-enamino ketones with fixed configurations, the cyclic 1,3-diketone (dimedone) 5 was chosen. The literature describes that dimedone enaminones have a complex reactivity that depends on the conditions employed, 14 which emphasizes the importance of the preparation of these compounds without by-products.…”

Section: Resultsmentioning

confidence: 99%

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Preparation of beta-enamino carbonylic compounds using microwave radiation/K-10

Braibante¹,

Braibante²,

Rosso³

et al. 2003

J. Braz. Chem. Soc.

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A preparação de uma série de β-enamino cetonas e ésteres empregando a metodologia de reações em suporte sólido associada à irradiação de microondas é descrita. As reações dos compostos β-dicarbonílicos cíclicos, acíclicos e α-cloro-substituídos, frente a aminas primárias ou aos acetatos de amônio correspondentes, foram efetuadas usando K-10 como suporte sólido e forno de microondas doméstico como fonte de irradiação, obtendo-se os β-enamino compostos com ótimos rendimentos.The preparation of β-enamino ketones and esters using the methodology of the reactions on solid support coupled with microwave irradiation is described. The reaction of cyclic, acyclic and α-chloro-substituted β-dicarbonyl compounds with amines or their corresponding ammonium acetates was carried out using K-10 as solid support and a domestic microwave oven as the radiation source to give β-enamino carbonylic compounds in good yields.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Preparation of beta-enamino carbonylic compounds using microwave radiation/K-10

Braibante¹,

Braibante²,

Rosso³

et al. 2003

J. Braz. Chem. Soc.

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show abstract

“…Bekanntermaßen reagieren N-Arylenamincarboxylate bevorzugt am a-C-Atom mit Elektrophilen; [15] dies wurde kürzlich auch bei einer Palladium-katalysierten Kupplung von Enaminonen mit Arylboraten beobachtet. [16] Ein plausibler Mechanismus (Schema 2) beginnt daher mit einer elektrophilen Palladierung am nucleophilen Enamin-Kohlenstoffatom, [17] gefolgt von Deprotonierung.…”

Section: Methodsunclassified

Palladium‐katalysierte oxidative Cyclisierung von N‐Aryl‐Enaminen: von Anilinen zu Indolen

et al. 2008

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“…[12][13][14] The use of K-10 or KSF as solid support avoids the use of the organic acids that favour the formation of by-products or cause the hydrolysis of the enamino carbonylic compounds.…”

Section: Methodsmentioning

confidence: 99%