71 research outputs found

    A Baker–Venkataraman retro-Claisen cascade delivers a novel alkyl migration process for the synthesis of amides

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    A simple extension of the carbamoyl Baker-Venkataraman rearrangement has been developed. If residual water in the reaction is not strictly excluded a Baker-Venkataraman retro-Claisen cascade takes place, giving amide products, in which an alkyl group apparently migrates between two functionalities of the substrate

    ortho-Lithiation Reactions of O-(3,n-Dihalophenyl) N,N-Diethylcarbamates: Synthesis of Dihalosalicylamides and 2,3,n-Trihalophenol Derivatives

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    New dihalosalicylamides and trihalophenol derivatives have been synthesized from easily available O-(3,n-dihalophenyl) N,N-diethylcarbamates by using a directed ortho-metalation (DoM) strategy. The o-lithiation reactions with sBuLi take place regioselectively at the doubly activated C-2 position, which demonstrates the ability of O-carbamates as directed metalating groups. In addition, highly functionalized arylnitriles were accessed from organolithium intermediates by using a tandem transnitrilation/SNAr reaction sequence.Junta de Castilla y LeĂłn (ConsejerĂ­a de EducaciĂłn) and FEDER (BU237U13 and BU076U16) as well as the Ministerio de EconomĂ­a y Competitividad (MINECO) and FEDER (CTQ2013-48937-C2-1-P

    Bifunctional acid-base ionic liquid for the one-pot synthesis of fine chemicals: thioethers, 2H-chromenes and 2H-quinoline derivatives

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    A bifunctional organocatalyst with ionic liquid properties and with an optimized distance between the acid and basic sites efficiently activates electron deficient olefins for 1,4 conjugated addition, which can be incorporated in different one-pot transformations for the preparation of cyclic and acyclic compounds of biological and synthetic interest. More specifically, the catalyst can be successfully applied for different carbon–carbon (Csingle bondC) and carbon–heteroatom (Csingle bondN, Csingle bondO, Csingle bondS) bond forming reactions integrated in a cascade sequence. The activity of the organocatalyst has been compared with that of structurally related monofunctional and bifunctional catalysts. The most attractive features of this procedure are the high atom economy and the use of inexpensive starting materials as well as the use of an environmentally friendly catalyst that can be easily recovered due to its ionic liquid properties.Financial support by Consolider-Ingenio 2010 (project MULTICAT), Spanish MICINN (Projects MAT2011-28009 and CTQ-201127550) and Program Severo Ochoa are gratefully acknowledged.Climent Olmedo, MJ.; Iborra Chornet, S.; Sabater Picot, MJ.; Vidal Castro, JD. (2014). Bifunctional acid-base ionic liquid for the one-pot synthesis of fine chemicals: thioethers, 2H-chromenes and 2H-quinoline derivatives. Applied Catalysis A: General. 481:27-38. https://doi.org/10.1016/j.apcata.2014.05.004S273848

    Fragment-Based Screening of the Bromodomain of ATAD2

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    Cellular and genetic evidence suggest that inhibition of ATAD2 could be a useful strategy to treat several types of cancer. To discover small-molecule inhibitors of the bromodomain of ATAD2, we used a fragment-based approach. Fragment hits were identified using NMR spectroscopy, and ATAD2 was crystallized with three of the hits identified in the fragment screen
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