Alkenylation of 1-acylindoles with olefins bearing electron-withdrawing substituents and palladium acetate

Itahara, Toshio; Ikeda, Mizue; Sakakibara, T.

doi:10.1039/p19830001361

Cited by 88 publications

(30 citation statements)

References 2 publications

(4 reference statements)

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“…Although catalytic olefination of indoles using Pd(OAc) 2 and Ag(I) and Cu(II) salts as the reoxidants was reported as early as 1983 by Itahara (Scheme 9),[17] several recent studies have greatly advanced this chemistry. Notably, Stoltz’s work using molecular oxygen as the reoxidant in the intramolecular olefination of indoles was a significant development (Scheme 10).…”

Section: Olefination Of Sp2 C–h Bonds: Pd(ii)/pd(0) Catalysismentioning

confidence: 99%

Palladium(II)‐Catalyzed CH Activation/CC Cross‐Coupling Reactions: Versatility and Practicality

et al. 2009

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In the past decade, palladium-catalyzed C-H activation/C-C bond forming reactions have emerged as promising new catalytic transformations; however, development in this field is still at an early stage compared to the state of the art in cross-coupling reactions using aryl and alkyl halides. This Review begins with a brief introduction of four extensively investigated modes of catalysis for forming C-C bonds from C-H bonds: Pd(II)/Pd(0), Pd(II)/Pd(IV), Pd(0)/Pd(II)/Pd(IV) and Pd(0)/ Pd(II) catalysis. More detailed discussion is then directed towards the recent development of Pd(II)-catalyzed coupling of C-H bonds with organometallic reagents through a Pd(II)/Pd(0) catalytic cycle. Despite much progress made to date, improving the versatility and practicality of this new reaction remains a tremendous challenge.

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Section: Olefination Of Sp2 C–h Bonds: Pd(ii)/pd(0) Catalysismentioning

confidence: 99%

Palladium(II)‐Catalyzed CH Activation/CC Cross‐Coupling Reactions: Versatility and Practicality

et al. 2009

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“…2,6-dichlorobenzamido-1 H -indole ( 5 ): MP: 125–127 °C, MP lit [193]: 131–131 °C. 1 H NMR (500 MHz, CDCl 3 ): δ 8.67 (d, J = 8.0 Hz, 1H), 7.62 (d, J = 8.0 Hz, 1H), 7.45–7.52 (m, 4H) 7.40 (m, 1 H) 6.84 (d, J = 3.5 Hz, 1H), 6.65 (d, J = 0.2 Hz, 1H) consistent with the literature [193].…”

Section: Experimental Materials and Methodsmentioning

confidence: 99%

Identification of HIV Inhibitors Guided by Free Energy Perturbation Calculations

Acevedo¹,

Ambrose²,

Flaherty³

et al. 2012

CPD

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Free energy perturbation (FEP) theory coupled to molecular dynamics (MD) or Monte Carlo (MC) statistical mechanics offers a theoretically precise method for determining the free energy differences of related biological inhibitors. Traditionally requiring extensive computational resources and expertise, it is only recently that its impact is being felt in drug discovery. A review of computer-aided anti-HIV efforts employing FEP calculations is provided here that describes early and recent successes in the design of human immunodeficiency virus type 1 (HIV-1) protease and non-nucleoside reverse transcriptase inhibitors. In addition, our ongoing work developing and optimizing leads for small molecule inhibitors of cyclophilin A (CypA) is highlighted as an update on the current capabilities of the field. CypA has been shown to aid HIV-1 replication by catalyzing the cis/trans isomerization of a conserved Gly-Pro motif in the N-terminal domain of HIV-1 capsid (CA) protein. In the absence of a functional CypA, e.g., by the addition of an inhibitor such as cyclosporine A (CsA), HIV-1 has reduced infectivity. Our simulations of acylurea-based and 1-indanylketone-based CypA inhibitors have determined that their nanomolar and micromolar binding affinities, respectively, are tied to their ability to stabilize Arg55 and Asn102. A structurally novel 1-(2,6-dichlorobenzamido) indole core was proposed to maximize these interactions. FEP-guided optimization, experimental synthesis, and biological testing of lead compounds for toxicity and inhibition of wild-type HIV-1 and CA mutants have demonstrated a dose-dependent inhibition of HIV-1 infection in two cell lines. While the inhibition is modest compared to CsA, the results are encouraging.

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“…Itahara and others [79][80][81][82][83][84][85][86] have reported the palladium-assisted synthesis of these indoles.The heteroannulation of N-tosyl-2-iodoaniline with a variety of oxygen substituted 1,3 dienes has been described by Larock and Guo [87].…”

Section: Synthesis Of Indolinesmentioning

confidence: 99%

Recent Uses of Palladium Chemistry in Indole Synthesis

Buolamwini¹

2006

COS

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Alkenylation of 1-acylindoles with olefins bearing electron-withdrawing substituents and palladium acetate

Cited by 88 publications

References 2 publications

Palladium(II)‐Catalyzed CH Activation/CC Cross‐Coupling Reactions: Versatility and Practicality

Palladium(II)‐Catalyzed CH Activation/CC Cross‐Coupling Reactions: Versatility and Practicality

Identification of HIV Inhibitors Guided by Free Energy Perturbation Calculations

Recent Uses of Palladium Chemistry in Indole Synthesis

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