40296-92-2Relevant articles and documents
Original antileishmanial hits: Variations around amidoximes
Tabélé, Clémence,Fai?es, Viviane dos S.,Grimaud, Fabien,Torres-Santos, Eduardo Caio,Khoumeri, Omar,Curti, Christophe,Vanelle, Patrice
, p. 154 - 164 (2018/02/20)
In continuation to our previous findings on amidoximes' antiparasitic activities, a new series of 23 original derivatives was designed and obtained by convergent synthesis. First, new terminal alkenes were synthesized by cross-coupling reaction. Then, cyclization was performed between terminal alkenes and β-ketosulfones using manganese(III) acetate reactivity. Twenty-three amidoximes were tested for their in vitro activity against Leishmania amazonensis promastigotes and their toxicity on murine macrophages. Seven of the tested compounds exhibited an antileishmanial activity at lower than 10 μM with moderate to low toxicity. Six of these molecules showed activity at lower than 10 μM against promastigotes and toxicity at higher than 50 μM were selected and evaluated for their activity against intracellular Leishmania amazonensis amastigotes. Modulating chemical substituents in position 2 of dihydrofuran highly influenced their antileishmanial activities. The introduction of a methyl or trifluoromethyl group on the benzene ring of the benzyl group had a positive influence on activity without significantly increasing toxicity (52, 59, 60).
Ligandless iron-catalyzed desulfinylative C-C allylation reactions using Grignard reagents and alk-2-enesulfonyl chlorides
Volla, Chandra M. R.,Markovic, Dean,Dubbaka, Srinivas Reddy,Vogel, Pierre
experimental part, p. 6281 - 6288 (2011/02/28)
Alk-2-enesulfonyl chlorides 1-4 were synthesized by the BCl3-promoted ene reaction of alkenes with SO2. These sulfonyl chlorides were then used as electrophilic partners in iron-catalyzed desulfinylative cross-coupling reactions with different Grignard reagents (aromatic, aliphatic, and heteroaromatic). The reaction can be catalyzed with even 2 mol-% of the simple iron salt Fe(acac)3. The regioselectivity of these allylations was studied by using sulfonyl chlorides 3 and 4 with aryl Grignard reagents. The scope of these allylations was further extended by the coupling of ester-substituted alk-2-enesulfonyl chloride 10 with aromatic Grignard reagents. Symmetrical products were synthesized by double C-C allylation with the use of 2-methylidenepropane-1,3-disulfonyl chloride (12). Wiley-VCH Verlag GmbH & Co. KGaA.
Palladium Complexes Containing Rigid Bidentate Nitrogen Ligands as Catalysts for Carbon-Carbon Bond Formation
Asselt, Rob van,Elsevier, Cornelis J.
, p. 323 - 334 (2007/10/02)
Zerovalent Pd(Ar-BIAN)(dimethyl fumarate) and divalent PdCl2(Ar-BIAN) complexes containing the rigid bidentate nitrogen ligand bis(arylimino)acenaphthene (Ar-BIAN; Ar = C6H5, p-MeC6H4, p-MeOC6H4) are efficient catalysts for the cross coupling reaction of various organic halides (including acyl-, allyl-, aryl-, benzyl-, vinyl- and 1,2-dienylhalides) with organomagnesium, -zinc and -tin reagents.Coupling reactions of organic halides with one equivalent of organomagnesium and -zinc reagents, in the presence of 1 mol percent of a Pd(Ar-BIAN) catalyst, generally proceed smoothly in THF at 20 degC, giving complete conversion of the starting halide within 1-16 hours.Good isolated yields of carbon-carbon coupled products are obtained and the ratio cross/homo coupling varies between 98/2 and 0/100, depending on the substrates used.Reactions employing organotin reagents proceed best in DMF or HMPA and need longer reaction times and/or higher temperatures, as compared to organomagnesium and -zinc reagents, to go to completion.The selectivity for cross coupling is high (generally >99 percent) and high isolated yields of cross coupled products can be obtained.In the presence of carbon monoxide (1-5 bar) ketones can be formed with excellent selectivity and in good yields, as was demonstrated for the carbonylative coupling of benzyl bromide with tetramethyltin or (p-tolyl)trimethyltin.Comparison of some Pd(Ar-BIAN) catalyzed reactions with Pd-phosphine catalyzed reactions reveals that these reactions complement each other: for example, when a Pd(Ar-BIAN) catalyst was employed, the coupling of 2-methylallyl chloride with phenyltributyltin was much faster, whereas the coupling of iodobenzene with vinyltrimethyltin was much slower, as compared to the Pd(PPh3)n catalyzed reactions.
