A Convenient Methodology for the N-Alkylation of Isatin Compounds

Garden, Simon J.; Torres, Javier Rodríguez; Silva, Leonardo E. da; Pinto, Ângelo C.

doi:10.1080/00397919808006872

Cited by 66 publications

(37 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…N-Propargylisatins, obtained from isatin and propargyl halides 79,85 , can be converted to N-acetonylisatins through hydration with Hg(II) salts in acidic media 86 .…”

Section: N-alkylationmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

Self Cite

834

447

View full text Add to dashboard Cite

Isatinas (1H-indol-2,3-diona) são compostos de grande versatilidade sintética, podendo ser utilizados na obtenção de diversos sistemas heterociclos, como derivados indólicos e quinolínicos, o que as tornam importantes matérias-primas na síntese de fármacos. Isatinas também têm sido detectadas em tecidos de mamíferos, o que tem despertado o interesse em seu estudo como moduladores em diversos processos bioquímicos. Os avanços na aplicação de isatinas em síntese orgânica, bem como na compreensão de seus efeitos biológicos e farmacológicos nos últimos vinte e cinco anos encontram-se relatados nesta revisão e seus respectivos materiais suplementares.Isatins (1H-indole-2,3-dione) are synthetically versatile substrates, where they can be used for the synthesis of a large variety of heterocyclic compounds, such as indoles and quinolines, and as raw material for drug synthesis. Isatins have also been found in mammalian tissue and their function as a modulator of biochemical processes has been the subject of several discussions. The advances in the use of isatins for organic synthesis during the last twenty-five years, as well as a survey of its biological and pharmacological properties are reported in this review and in the accompanying supplementary information.

show abstract

“…N-Propargylisatins, obtained from isatin and propargyl halides 79,85 , can be converted to N-acetonylisatins through hydration with Hg(II) salts in acidic media 86 .…”

Section: N-alkylationmentioning

confidence: 99%

The chemistry of isatins: a review from 1975 to 1999

Silva¹,

Garden²,

Pinto³

2001

J. Braz. Chem. Soc.

Self Cite

834

447

View full text Add to dashboard Cite

show abstract

“…The method has been applied successfully to anilines with electron-withdrawing substituents, such as 2-fluoroaniline (Smolders et al, 1982) (Scheme 1). Compounds 3,5,8, and 11 were produced via N-alkylation of corresponding starting material with CaH 2 in dimethyl formamide (DMF; Garden et al, 1998) in the presence of iodomethane. The reaction mixture was kept at 1008C for 4 h. After treatment with 0.5 M hydrochloric acid, the isatins were obtained in 90%, 85%, 88%, and 92% yields, respectively.…”

Section: Visual Inspection Of the Minimized Ligand-protein Complexesmentioning

confidence: 99%

“…N-methylisatins (Garden et al, 1998) and N-acetylisatins (Sumpter and Jones, 1943) were prepared from their corresponding isatins by methods described in the literature.…”

Section: General Proceduresmentioning

confidence: 99%

Design, synthesis, and biological evaluation of new 3-hydroxy-2-oxo-3-trifluoromethylindole as potential HIV-1 reverse transcriptase inhibitors

et al. 2007

View full text Add to dashboard Cite

The trifluoromethyl group (CF 3 ) is present in commercially available drugs of various therapeutic classes owing to its ability to modify and frequently improve their biological activities. Efavirenz is a trifluoromethylated inhibitor of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase (RT) that shows good results in anti-HIV chemotherapy. With the objective of developing efficient non-nucleoside compounds, we have designed and synthesized some new 3-hydroxy-2-oxo-3-trifluoromethylindole as potential RT inhibitors. We used different substituted isatins as starting materials. The final products contain the group CF 3 , present in Efavirenz, and a pharmacophoric group, oxoindole. We have used molecular docking with HIV-1 RT as a tool to design putative non-nucleoside reverse transcriptase inhibitors (NNRTIs). Based on the calculation results obtained, a series of new 3-hydroxy-2-oxo-3-trifluoromethylindoles were synthesized as a novel class of potential RT inhibitors. The results showed that these compounds are capable of important interactions with the NNRT binding site, which encouraged us

show abstract

“…The method also allows the preparation of alkyl-(entries 13-16) or acyl-(entry 12) N-substituted anthranilic acids. It should be noted that N-alkylation of isatins is a simple process (Wang et al 2012, Garden et al 1998, whereas anthranilic acid N-alkylation often requires drastic reaction conditions and the use of expensive catalysts (Hikawa and Yokoyama 2011). …”

Section: Introductionmentioning

confidence: 99%

Anthranilic acids from isatin: an efficient, versatile and environmentally friendly method

Rio

Silva

Martinez

et al. 2015

An. Acad. Bras. Ciênc.

Self Cite

View full text Add to dashboard Cite

This paper describes the preparation of a series of 16 anthranilic acids in yields ranging from 51 to 97%, by treating the isatins with NaOH and H 2 O 2 . Independently of the nature of the substituent on the aromatic ring, the reactions were complete in 15 min at room temperature, whereas those of isatins containing a substituent on the nitrogen atom required longer reaction time for completion (45 min) under the same reaction conditions.

show abstract

A Convenient Methodology for the N-Alkylation of Isatin Compounds

Cited by 66 publications

References 16 publications

The chemistry of isatins: a review from 1975 to 1999

The chemistry of isatins: a review from 1975 to 1999

Design, synthesis, and biological evaluation of new 3-hydroxy-2-oxo-3-trifluoromethylindole as potential HIV-1 reverse transcriptase inhibitors

Anthranilic acids from isatin: an efficient, versatile and environmentally friendly method

Contact Info

Product

Resources

About