- Heterogeneous Catalysis with Basic Compounds to Achieve the Synthesis and C-N Cleavage of Azetidin-2-ones under Microwave Irradiation
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The synthesis of azetidin-2-ones with a completely heterogeneous catalysis is reported. The use of basic compounds as solid catalysts allowed for the synthesis of azetidin-2-ones under microwave irradiation without organic additives such as triethylamine. An excellent catalyst for this transformation was Mg-Al hydroxide (MAH). The present methodology offers the advantages of non-hazardous reaction conditions, short reaction times, high yields, and catalyst reusability. Different substitution groups were tested on the imines and acyl chlorides to explore the scope of the reaction. Unconventional N-C4 bond cleavage was detected in azetidin-2-ones. MAH was characterized by N 2 adsorption-desorption, X-ray diffraction (XRD), scanning electron microscopy (SEM), and high-resolution transmission electron microscopy (HR-TEM).
- Alcaraz, Yolanda,Cruz, Francisco,De La Cruz, Fabiola N.,Delgado, Francisco,Domínguez, José Manuel,Galván, Adriana,Gomez, Clarisa Villegas,Martínez, Merced,Vázquez, Miguel A.
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p. 3625 - 3637
(2019/09/30)
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- Biological activity of 3-chloro-azetidin-2-one derivatives having interesting antiproliferative activity on human breast cancer cell lines
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Resveratrol (3,4′,5 tri-hydroxystilbene), a natural plant polyphenol, has gained interest as a non-toxic agent capable of inducing tumor cell death in a variety of cancer types. However, therapeutic application of these beneficial effects remains very lim
- Chimento, Adele,Sala, Marina,Gomez-Monterrey, Isabel M.,Musella, Simona,Bertamino, Alessia,Caruso, Anna,Sinicropi, Maria Stefania,Sirianni, Rosa,Puoci, Francesco,Parisi, Ortensia Ilaria,Campana, Carmela,Martire, Emilia,Novellino, Ettore,Saturnino, Carmela,Campiglia, Pietro,Pezzi, Vincenzo
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p. 6401 - 6405
(2013/11/19)
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- ELECTROCHEMICAL STUDIES ON Β-LACTAMS. PART 4. ELECTROACETYLATION OF Β-LACTAMS.
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Electroreduction of 3-bromo- and 3,3-dichloro-β-lactams 1 carried out at the potential of the first voltammetric peak and in the presence of acetic anhydride gives 3-acetyl-β-lactams 2.The electrosynthesis is highly stereoselective, as only the acetyl der
- Casadei, Maria Antonietta,Inesi, Achille,Moracci, Franco Micheletti,Occhialini, Donatella
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p. 6885 - 6890
(2007/10/02)
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- Electrochemical Studies on β-Lactams. Part 1. Electroreduction of 3-Halogeno-β-lactams
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The electrochemical reduction in aprotic solvents of 3-halogeno-β-lactams (1a-c) and (2a-c), with or without added proton donors or/and electrophiles, has been investigated.Without added substrates, the carbanion arising from the cleavage of the carbon-halogen bond undergoes protonation (mainly from the 'parent'molecule) and, completely, ring-opening reactions yielding the corresponding dehalogenated β-lactam and α,β-unsaturated amide.In the presence of proton donors (CH3CO2H) or electrophiles (CO2), the protonation and coupling reactions, respectively, become largely predominant, and the dehalogenated or carboxylated β-lactams are the main products.In the presence of BrCH2CH2CN the protonation reaction is preferred, and the dehalogenated β-lactam predominates over the substitution product.The high yields of 3-carboxy-β-lactams, a class of compounds not easily accessible by chemical methods, are noteworthy from a synthetic point of view.
- Casadei, Maria Antonietta,Moracci, Franco Micheletti,Inesi, Achille
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p. 419 - 424
(2007/10/02)
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- Reactions of (E)-1-Methoxy-1-trimethylsiloxyprop-1-ene with Acyl Isocyanates and Acyl Isothiocyanates
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Reaction of aryl acyl,and alkyl acyl isocyanates with (E)-1-methoxy-1-trimethylsiloxyprop-1-ene affords high yields of various methyl 3-acylamino-2-methyl-3-oxopropanoates.The corresponding acyl isothiocyanates give a variety of products depending on the structure of the isothiocyanate.
- Cambie, Richard C.,Davis, Paul F.,Rutledge, Peter S.,Woodgate, Paul D.
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p. 2073 - 2084
(2007/10/02)
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