Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Valois‐Escamilla, Ismael; Álvarez‐Hernández, Alejandro; Rangel-Ramos, Luis Felipe; Suárez‐Castillo, Oscar R.; Ayala-Mata, Francisco; Zepeda, L. Gerardo

doi:10.1016/j.tetlet.2011.05.040

Cited by 11 publications

(4 citation statements)

References 70 publications

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“…13 C{ 1 H} NMR (125 MHz, CDCl 3 /DMSO) δ 138.8, 137.9, 132.1, 128.9, 128.0, 127.7, 125.3, 123.1, 121.6, 115.2, 114.0, 99.3. The spectral data are in agreement with those reported in the literature …”

Section: Experimental Sectionsupporting

confidence: 91%

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

2020

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Imidoyl sulfoxonium ylides are presented for the first time as potential precursors to generate α-imino metal-carbene intermediates and applied in direct C–H functionalization reactions catalyzed by [Ir(cod)Cl]2 (4 mol %) to provide 2-substituted indoles (up to 70% yield) in just one step. This class of sulfur ylide is successfully obtained from imidoyl chloride and dimethylsulfoxonium methylide (23 new examples in 45–85% yield) or by imino group formation from the corresponding β-keto sulfoxonium ylides and anilines in the presence of TiCl4 as a Lewis acid (9 examples in 33–94% yield).

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Section: Experimental Sectionsupporting

confidence: 91%

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

2020

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“…Synthesis of Methyl 5‐Bromo‐2‐iodobenzoate (Procedure A): , 2‐Iodobenzoic acid (6.20 g, 25.0 mmol, 1.00 equiv.) was taken up in concentrated H 2 SO 4 (50 mL), and heated to 60 °C.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Characterization, and Reaction of a Both Inter‐ and Intramolecularly Coordinated Pseudocyclic Iodosylbenzene–Trifluoroacetic Acid Complexes

et al. 2018

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An ortho‐substituted ether‐oxygen‐coordinated pseudocyclic iodosylbenzene‐trifluoroacetic acid (pcISB‐TFA) complex was synthesized and characterized by X‐ray crystallographic analysis. TFA suppresses the disproportionation by both coordination of the oxygen atom to the iodine(III) center through secondary bonding and by hydrogen bonding to the oxygen anion. This bench‐stable reagent is highly soluble in common organic solvents and reacts with various organic substrates under mild reaction conditions to give the corresponding products in good yields.

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“…Anal. (C 23 H 20 FNO 3 S (409.47)) C, H, F, N, S.7-Methoxy-2-phenyl-3-((3,4,5-trimethoxyphenyl)thio)-1H-indole(42). Synthesized as 6, starting from 7-methoxy-2-phenyl-1H-indole(61).…”

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confidence: 99%

New indolylarylsulfones as highly potent and broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitors

Famiglini

Regina

Coluccia

et al. 2014

European Journal of Medicinal Chemistry

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New indolylarylsulfone HIV-1 NNRTIs were synthesized to evaluate unexplored substitutions of the benzyl/phenylethyl group linked at the indole-2-carboxamide. Against the NL4-3 HIV-1 WT strain, 17 out 20 compounds were superior to NVP and EFV. Several compounds inhibited the K103N HIV-1 mutant strain at nanomolar concentration and were superior to EFV. Some derivatives were superior to EFV against the Y181C and L100I HIV-1 mutant strains. Against the NL4-3 HIV-1 strain, the enantiomers 24 and 25 showed small differences of activity. In contrast, 24 turned out significantly more potent than 25 against the whole panel of mutant HIV-1 strains. The docking studies suggested that the difference in the observed inhibitory activities of 24 and 25 against the K03N mutation could be due to a kinetic rather than affinity differences.

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Synthesis of 6-bromo-2-arylindoles using 2-iodobenzoic acid as precursor

Cited by 11 publications

References 70 publications

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

α-Imino Iridium Carbenes from Imidoyl Sulfoxonium Ylides: Application in the One-Step Synthesis of Indoles

Synthesis, Characterization, and Reaction of a Both Inter‐ and Intramolecularly Coordinated Pseudocyclic Iodosylbenzene–Trifluoroacetic Acid Complexes

New indolylarylsulfones as highly potent and broad spectrum HIV-1 non-nucleoside reverse transcriptase inhibitors

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