25 research outputs found

    Direct Access to Fluorinated Thiadiazolo[3,2-a]pyrimidin-7-one Systems

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    International audienceA mild, simple method for the regioselective synthesis of thiadiazolo[3,2-a]pyrimidin-7-ones bearing a perfluoroalkyl group is reported. In order to study the core reactivity, various nucleophile substitutions were performed involving the reactive carbon-bromide bond via a one-pot strategy

    Mild and Direct Access to 7-Substituted-4-trifluoromethylpyrimido[1,2-b]pyridazin-2-one Systems

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    International audienceNew and efficient methods for the synthesis of 7-substituted-4-trifluoromethylpyrimido[1,2-b]pyridazin-2-one derivatives using either two-step Suzuki/heterocyclization, or two-step heterocyclization/substitution sequences are developed. A variety of substituted products are obtained in good to excellent yields from 3-amino-6-chloropyridazine and ethyl 4,4,4-trifluorobut-2-ynoate

    An Easy Stereoselective Copper(I)-Catalyzed Synthesis of (E)-3-Trifluoromethylbut-2-en-3-ynoate via Palladium-Free Stille Coupling Reaction

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    International audienceA general and efficient Cu(I)-catalyzed cross-coupling reaction of alkynyl bromides and beta-tributylstannyl-alpha, beta-unsaturated ester bearing a trifluoromethyl group in beta-position was developed under very mild conditions. This method provides easy access to a variety of 2,3-enynoate bearing a trifluoromethyl group from good to excellent yields with excellent stereoselectivity. This procedure does not require the use of any expensive supplementary additives and is palladium-free

    Gold-silver catalyzed straightforward one pot synthesis of pyrano[3,4- b]pyrrol-7(1H)-ones

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    CommunicationInternational audiencePyrano[3,4-b]pyrrol-7(1H)-one is a bicyclic structure that is rarely described in the literature but found in numerous polycyclic natural products as Lamellarins. This work presents an one-pot synthesis of pyrano[3,4-b]pyrrol-7(1H)-one substituted in 2-and 5-position. The reaction proceeds via a one-pot two steps 5-endo-dig and 6-endo-dig cyclizations catalyzed by a cationic gold complex with high regioselectivity

    Short and convenient synthesis of two natural phthalides by a copper(I) catalysed Sonogashira/oxacyclisation copper(I) process

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    International audienceTotal synthesis of (+/-)-herbaric acid and (+/-)-(4-methoxybenzyl)-5,7-dimethoxyphthalide, two natural phthalide products, was achieved in 8 steps and 5 steps, respectively, starting from commercially available 3,5-dimethoxyaniline. The key step of the sequence included a copper-catalysed tandem cross-coupling and oxacylisation reaction of terminal alkynes and 2-iodobenzok acid derivatives via 5-exo-dig cyclisation with high stereo-, regio- and chemoselectivities. This straightforward method allows the preparation of diverse phthalides, which belong to a group of pharmacologically important compounds
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