RESUMEN
In recent years, isoquinoline-1,3(2H,4H)-dione compounds have attracted extensive attention from synthetic chemists, with the aim of finding simple, mild, green and efficient synthetic methods. In this review, we summarize the diverse range of synthetic methods employing acryloyl benzamides as key substrates to furnish isoquinoline-1,3-diones using different radical precursors, such as those containing carbon, sulphur, phosphorus, nitrogen, silicon and bromine. This will stimulate the interest of readers to engage in research in this field.
Asunto(s)
Bromo , Silicio , Isoquinolinas/química , Benzamidas/química , Nitrógeno , Fósforo , Azufre , CarbonoRESUMEN
A Cu(i)-catalyzed cross-coupling of primary amines with 2,2'-dibromo-1,1'-biphenyl for the synthesis of polysubstituted carbazole has been achieved. This protocol provides an efficient strategy for the synthesis of carbazole using cheap copper catalysts with diamine ligand, and it provides convenient access to a series of carbazole derivatives in moderate yields.
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Nitrogen-containing heterocycles are ubiquitous fragments of numerous natural products, pharmaceuticals, designed bioactive drug candidates and agrochemicals. During the past few decades, these compounds have received considerable attention from the synthetic chemistry community, and great efforts have been focused on the development of concise and efficient methods for the synthesis of these heterocyclic skeletons. In this review, we summarize a diverse range of synthetic methods employing ß-aminovinyl esters(ketones) as key CîC-N-synthons to furnish useful bioactive heterocyclic frameworks, such as quinolines, pyridines, pyrazines, pyrroles, indoles, oxazoles, imidazoles, thiazoles, isothiazoles, pyrazoles, triazoles, and azepines, thus offering new opportunities and expanding the toolbox of synthetic chemistry reactions.
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Phosphoramide, as an important framework of many biologically active molecules, has attracted widespread attention in recent decades. It is not only widely used in pharmaceuticals because of its excellent biological activities, but it also shows good performance in organic dyes, flame retardants and extractors. Thus, it is of great significance to develop effective and convenient methods for the synthesis of phosphoramides. In this review, the recent advancements made in the synthesis routes and applications of phosphoramides are discussed. The synthetic strategies of phosphoramides can be separated into five categories: phosphorus halides as the substrate, phosphates as the substrate, phosphorus hydrogen as the substrate, azides as the substrate and other methods. The latest examples of these methods are provided and some representative mechanisms are also described.
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An effient tandem process consisting of palladium-catalyzed double-bond isomerization of long-chain olefins and subsequent intramolecular cyclization promoted by B2(OH)2 for the synthesis of aromatic oxazaheterocycles is disclosed. This strategy can also provide rapid access to pyrido[3,4-b]indoles, trans-2-olefins, and eneamides bearing various functional groups with high regio- and stereoselectivity.
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Indoles , Paladio , Alquenos , Catálisis , Ciclización , Isomerismo , Estructura MolecularRESUMEN
The palladium-N-heterocyclic carbene (NHC)-catalyzed allylic alkylation of various pronucleophiles with alkynes has been accomplished under mild conditions. The protocol exhibits broad functional group compatibility and high atom economy. Moreover, the catalytic process avoids the use of external oxidants and acid as additives.
RESUMEN
A new and efficient catalytic approach to the synthesis of 3-acylindoles under Pd-Cu-cocatalyzed oxidative conditions is demonstrated. tert-Butyl hydroperoxide (TBHP) acts not only as the oxidant, but also as an oxygen source in the approach. The process allows quick and atom-economical assembly of 3-acylindoles from readily available starting materials and tolerates a broad range of functional groups.
Asunto(s)
Cobre/química , Indoles/química , Paladio/química , Catálisis , Ciclización , Indoles/síntesis química , Acoplamiento OxidativoRESUMEN
Highly substituted benzene derivatives, including alkoxy-, iodoalkoxy-, and diiodo-substituted benzenes, can be selectively synthesized via Brønsted acid catalyzed and iodine-promoted tandem carbocyclization respectively. This reaction involved a direct process for C-C bond formation from 5,2-enyn-1-ones, and different reaction systems (Brønsted acids/electrophiles with solvents) afforded different substituted benzenes. Furthermore, the halogenated moiety and alkoxy group can be readily introduced into the benzene in a position which has not been easily obtained previously.
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Ácidos/química , Alquenos/química , Alquinos/química , Benceno/síntesis química , Yodo/química , Cetonas/química , Benceno/química , Catálisis , Ciclización , Estructura MolecularRESUMEN
A domino reaction via palladium-catalyzed Sonogashira coupling of benzimidoyl chlorides with 1,6-enynes and then cyclization to form quinoline derivatives has been developed. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed. The procedure is simple, rapid, and general, and the substrates are readily available.
Asunto(s)
Alquinos/química , Benzamidas/química , Paladio/química , Quinolinas/síntesis química , Catálisis , Ciclización , Espectroscopía de Resonancia Magnética , Estructura Molecular , Quinolinas/química , Relación Estructura-ActividadRESUMEN
A mild and direct process for C-C bond formation from propargylic alcohols and olefin has been developed in the presence of a silver catalyst. In this reaction, trace amounts of water were necessary and allene alcohols 2 and 1,3-dienes 3 were obtained selectively.
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Alquenos/química , Alquinos/química , Carbono/química , Propanoles/química , Antimonio/química , Catálisis , Cristalografía por Rayos X , Ciclización , Estructura Molecular , Plata/químicaRESUMEN
Ag-catalyzed cyclization of 2-alkynyl benzyl azides offers a novel and efficient method for the synthesis of substituted isoquinoline. The reaction proceeds smoothly in moderate to good yields and tolerates considerable functional groups. The reaction conditions and the scope of the process are examined, and a plausible mechanism is proposed.
Asunto(s)
Azidas/química , Benceno/química , Isoquinolinas/síntesis química , Plata/química , Alquilación , Catálisis , Ciclización , Electrones , Isoquinolinas/química , Estructura MolecularRESUMEN
A facile and efficient synthesis of 1,3-diaryl-5-spirohexahydropyrimidines via a one-pot condensation of anilines, formaldehyde, and cyclohexanones is reported. In this one-pot, three-component reaction, six molecules of reactants are involved and six new covalent bonds are generated. Bicyclic products are obtained from the starting materials in one pot using readily available starting materials and catalysts.