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1.
Org Biomol Chem ; 20(40): 7861-7885, 2022 10 19.
Artigo em Inglês | MEDLINE | ID: mdl-36185038

RESUMO

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.


Assuntos
Bromo , Silício , Isoquinolinas/química , Benzamidas/química , Nitrogênio , Fósforo , Enxofre , Carbono
2.
RSC Adv ; 12(37): 24232-24236, 2022 Aug 22.
Artigo em Inglês | MEDLINE | ID: mdl-36128530

RESUMO

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.

3.
Org Biomol Chem ; 20(2): 282-295, 2022 01 05.
Artigo em Inglês | MEDLINE | ID: mdl-34877952

RESUMO

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 CC-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.

4.
Org Biomol Chem ; 19(47): 10296-10313, 2021 12 08.
Artigo em Inglês | MEDLINE | ID: mdl-34812834

RESUMO

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.

5.
J Org Chem ; 86(15): 10032-10042, 2021 08 06.
Artigo em Inglês | MEDLINE | ID: mdl-34279106

RESUMO

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.


Assuntos
Indóis , Paládio , Alcenos , Catálise , Ciclização , Isomerismo , Estrutura Molecular
6.
Org Lett ; 21(19): 7956-7960, 2019 Oct 04.
Artigo em Inglês | MEDLINE | ID: mdl-31513418

RESUMO

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.

7.
Chem Commun (Camb) ; 49(14): 1410-2, 2013 Feb 18.
Artigo em Inglês | MEDLINE | ID: mdl-23310929

RESUMO

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.


Assuntos
Cobre/química , Indóis/química , Paládio/química , Catálise , Ciclização , Indóis/síntese química , Acoplamento Oxidativo
8.
J Org Chem ; 77(20): 9029-37, 2012 Oct 19.
Artigo em Inglês | MEDLINE | ID: mdl-22991941

RESUMO

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.


Assuntos
Ácidos/química , Alcenos/química , Alcinos/química , Benzeno/síntese química , Iodo/química , Cetonas/química , Benzeno/química , Catálise , Ciclização , Estrutura Molecular
9.
J Org Chem ; 75(4): 1305-8, 2010 Feb 19.
Artigo em Inglês | MEDLINE | ID: mdl-20088585

RESUMO

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.


Assuntos
Alcinos/química , Benzamidas/química , Paládio/química , Quinolinas/síntese química , Catálise , Ciclização , Espectroscopia de Ressonância Magnética , Estrutura Molecular , Quinolinas/química , Relação Estrutura-Atividade
10.
Org Lett ; 11(15): 3206-9, 2009 Aug 06.
Artigo em Inglês | MEDLINE | ID: mdl-19572605

RESUMO

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.


Assuntos
Alcenos/química , Alcinos/química , Carbono/química , Propanóis/química , Antimônio/química , Catálise , Cristalografia por Raios X , Ciclização , Estrutura Molecular , Prata/química
11.
J Org Chem ; 74(7): 2893-6, 2009 Apr 03.
Artigo em Inglês | MEDLINE | ID: mdl-19271738

RESUMO

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.


Assuntos
Azidas/química , Benzeno/química , Isoquinolinas/síntese química , Prata/química , Alquilação , Catálise , Ciclização , Elétrons , Isoquinolinas/química , Estrutura Molecular
12.
J Org Chem ; 72(22): 8600-3, 2007 Oct 26.
Artigo em Inglês | MEDLINE | ID: mdl-17918899

RESUMO

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.


Assuntos
Cicloexanonas/química , Formaldeído/química , Piridinas/química , Pirimidinas/síntese química , Cristalografia por Raios X , Modelos Moleculares , Estrutura Molecular , Pirimidinas/química , Estereoisomerismo
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