21615-74-7Relevant articles and documents
Application of a new solid-phase resin: Benzamide ortho-lithiation and the synthesis of a phthalide library
Garibay, Patrick,Toy, Patrick H.,Hoeg-Jensen, Thomas,Janda, Kim. D.
, p. 1438 - 1440 (1999)
The utility of new polytetrahydrofuran cross-linked polystyrene resins is demonstrated through the solid-phase synthesis of a phthalide library. The phthalides are synthesized via directed ortho-lithiation of resin bound benzamides and isolated via cyclat
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Ferrari et al.
, p. 1247,1251 (1965)
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Chatterjea et al.
, p. 3409 (1972)
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Efficient One-Pot Synthesis of 3-Substituted Phthalides via Additive Arylation of Organozinc Intermediate
Hasan, Mohsin,Tonk, Rajiv Kumar,Yadav, Vivek
, p. 783 - 789 (2022/02/17)
In recent years, substitution at the third position on phthalides has been proven a valua-ble synthetic intermediate for developing active molecules. We reported a direct and efficient one-pot method for the synthesis of 3-aryl Phthalides performed by adding organo-zinc reagent on methyl-2-formylbenzoate; reagent formed in-situ by the reaction between diethylzinc and different aryl boronic acid derivatives without using any ligand. The possible mechanism involved a coordi-nated zinc carbonyl transition state, arylation, and followed by the intramolecular cyclization. The substituents groups in boronic having different electronic and steric properties played an important role in the reaction completion time and yield. The structure elucidation and confirmation of the synthesized compounds were done by using H-NMR analytical data. The method can be useful for synthesizing various scaffolds and intermediates in search of potentially active compounds.
Transition-Metal-Free Synthesis of Polyfunctional Triarylmethanes and 1,1-Diarylalkanes by Sequential Cross-Coupling of Benzal Diacetates with Organozinc Reagents
Wei, Baosheng,Ren, Qianyi,Bein, Thomas,Knochel, Paul
supporting information, p. 10409 - 10414 (2021/03/26)
A variety of functionalized triarylmethane and 1,1-diarylalkane derivatives were prepared via a transition-metal-free, one-pot and two-step procedure, involving the reaction of various benzal diacetates with organozinc reagents. A sequential cross-coupling is enabled by changing the solvent from THF to toluene, and a two-step SN1-type mechanism was proposed and evidenced by experimental studies. The synthetic utility of the method is further demonstrated by the synthesis of several biologically relevant molecules, such as an anti-tuberculosis agent, an anti-breast cancer agent, a precursor of a sphingosine-1-phosphate (S1P) receptor modulator, and a FLAP inhibitor.
