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Wordingham, Synthesis, This allows for straightforward construction of complex polyaryl systems, an attractive method for library synthesis of drug targets containing functionalized pyridine moieties. A recyclable, convenient, and efficient catalytic system allows the C-acylation of 1,3-dicarbonyl compounds and malononitrile with acid chlorides in moderate to excellent yields under mild conditions.
The key to accelerate such a double Reformatsky reaction is considered to be a complex-induced proximity effect of the in situ generated zinc alkoxide coordinated with a bidentate amine.
A convenient two-step preparation of alkylidenepyrrolidines is reported. A feature of the reaction system is its high tolerance of functional groups due to the moderate nucleophilicity of organozinc reagents. Addition of ammonia to 7 followed by dehydration via 8 generates the imine intermediate 9.
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A particularly simple and efficient acylation with N-acylbenzotriazoles and O-Pfp esters can be conducted in untreated, reagent-grade CH2Cl2 open to the air. Related A short, mild, and highly chemoselective addition of organolithium reagents to BF2 complexes of 3-oxopropanoates allows a straightforward preparation 1,3-diketones.
The reaction provides valuable dithianes with controlled formation of a new C-C bond and a C-O bond via a radical coupling pathway. Reactions of both aromatic and aliphatic acid chlorides and bis acid chlorides were conducted. Various 1,3,5-tricarbonyl derivatives were prepared by a mild reaction of 1,3-bis silyl enol ethers with acid chlorides.
Additionally, electron-withdrawing groups and electron-donating groups on the incoming aryl substituents are both well tolerated. InTu and coworkers developed a 3 fragment, one-pot combinatorial strategy for developing 3-cyanoterpyridines 34and 1-aminoacylterpyridines This methodology would also be advantageous for biological assays and screening experiments.
The benzylic position of 41 was methylated and subsequent SnAr reaction with potassium diphenylphosphide to generate ligand The pyridinium cation is then eliminated to form hydroxy-dienamine These acyl pyridine are attractive intermediates because they have an electrophilic handle that allows for additional functionality to be incorporated into the molecule.
For example, the Chichibabin synthesis requires 2 equivalents of unsaturated starting material. Aromatization of 12 via subsequent loss of water generates the 1 3 dicarbonyl synthesis pyridine heterocycle