Person: Lázaro Milla, Carlos
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First Name
Carlos
Last Name
Lázaro Milla
Affiliation
Universidad Complutense de Madrid
Faculty / Institute
Ciencias Químicas
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Item Estudio de la reactividad de sistemas insaturados frente a zwitteriones tipo koshar. Aplicaciones sintéticas(2020) Lázaro Milla, Carlos; Alcaide Alañón, Benito; Almendros Requena, PedroKoshar’s zwitterions have not been studied since 1976. Fortunately, in 2013 Yanai’s group rediscovered them, improving their synthesis and performing a deep analysis of their properties and characteristics. This work was the starting point of a new research line in our group and hasled to the present PhD Thesis. The in situ formation of the molecule Tf2C=CH2 in solution, from Koshar’s zwitterions, made us consider the study of its behavior and synthetic utility with different unsaturated groups and heterocyclic systems. On the other hand, the development of cyclization methodologies to obtain highly tensioned rings is of great interest. Cyclobutenes, cyclobutenones and cyclobutenols are included in this group. These four-membered carbocycles are molecules with great synthetic utility but difficult to access; and particularly if their formation is required with chemo-, regio- and stereoselectivity...Item Cobalt(I)-Catalyzed (3 + 2 + 2) Cycloaddition between Alkylidenecyclopropanes, Alkynes, and Alkenes(Organic letters, 2023) Da Concepción, Eduardo; Mascareñas, José L.; López, Fernando; Lázaro Milla, Carlos; Fernández López, IsraelCobalt(I) catalysts equipped with bisphosphine ligands can be used to promote formal (3 + 2 + 2) intramolecular cycloadditions of enynylidenecyclopropanes of type 1. The method provides synthetically appealing 5,7,5-fused tricyclic systems in good yields and with complete diastereo- and chemoselectivity. Interestingly, its scope differs from that of previously reported annulations based on precious metal catalysts, specifically rhodium and palladium. Noticeably, density functional theory calculations confirm that the mechanism of the reaction is also different from those proposed for these other catalysts.Item Synthesis of polycyclic aromatic hydrocarbons decorated by fluorinated carbon acids/carbanions(Chemistry a European Journal, 2021) Hoshikawa, Shoki; Yanai, Hikaru; Martín‐Mejías, Irene; Lázaro Milla, Carlos; Aragoncillo Abanades, Cristina; Almendros Requena, Pedro; Matsumoto, TakashiThe carboarylation reaction of biphenyl‐alkynes was successfully triggered by electrophilic attack of 1,1‐bis(triflyl)ethylene on the alkyne moiety to give polycyclic aromatic hydrocarbons (PAHs) decorated by superacidic carbon acid functionality. Neutralisation of thus obtained acids with NaHCO3 yielded the corresponding sodium salts, which showed improved solubility in both aqueous and organic solvents.Item Transition metal-free controlled synthesis of bis[(trifluoromethyl)sulfonyl]ethyl-decorated heterocycles(Organic Chemistry Frontiers, 2018) Almendros Requena, Pedro; Yanai, Hikaru; Hoshikawa, Shoki; Aragoncillo Abanades, Cristina; Lázaro Milla, Carlos; Toledano-Pinedo, Mireia; Matsumoto, Takashi; Alcaide Alañón, BenitoSeveral heterocycles reacted with shelf-stable 2-(2-fluoropyridinium-1-yl)-1,1-bis[(trifluoromethyl)sulfonyl] ethan-1-ide, a latent Tf2CvCH2 source, to give rise in a mild and controllable way to adducts via direct C–H bis[(trifluoromethyl)sulfonyl]ethylation reactions. This metal- and irradiation-free protocol is convenient. Besides, the volatile side-product 2 fluoropyridine can be smoothly eliminated under vacuum, which facilitates purification. The substrate scope survey discloses that exquisite chemo- and regioselectivities are achieved in a variety of heterocyclic systems. Of particular interest are the late-stage structural modification of known pharmaceuticals, such as the marketed drugs Phenazone (Antipyrine) and Edaravone, and the development of a water soluble fluorescent dye.Item Straightforward Synthesis of Bis[(trifluoromethyl)sulfonyl]ethylated Isocoumarins from 2-Ethynylbenzoates(Journal of Organic Chemistry, 2023) Petcu, Sonia; Lázaro Milla, Carlos; Rodríguez, Javier; Iriepa, Isabel; Bautista-Aguilera, Óscar ; Aragoncillo Abanades, Cristina; Alonso Gómez, José Miguel; Almendros Requena, PedroHerein, we report a facile isocoumarin and isoquinolone preparation by taking advantage of an initial bis(triflyl)ethylation [triflyl = (trifluoromethyl)sulfonyl] reaction, followed by heterocyclization, which contrasts with our previous results on cyclobutene formation. The efficiency of the catalyst- and irradiation-free heterocyclization/bis(triflyl)ethylation sequence showed exquisite dependence on the electronic nature of the substituents at the 2-ethynylbenzoate(benzamide) precursors. Molecular docking of model bis(triflyl)ethylated isocoumarins on human acetylcholinesterase (hAChE) revealed promising biological activities through selective coordination on both the catalytic active site and peripheral active site.