Palladium-catalysed cyclisation of 2-substituted halogenoarenes by dehydrohalogenation

Ames, D. E.; Opalko, A.

doi:10.1016/s0040-4020(01)91149-4

Cited by 238 publications

(111 citation statements)

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“…One of the earliest examples of intramolecular direct arylation of a heteroarene with one heteroatom bearing a (hetero)aryl halide tether was reported in 1984 by Ames and Opalko. [209] They described that treatment of 2-(2-bromophenoxy)pyridine (313) with 10 mol% PdA C H T U N G T R E N N U N G (OAc) 2 in DMA at 170 8C for 48 h in the presence of Na 2 CO 3 as the base gave benzofurano-A C H T U N G T R E N N U N G [2,3-b]pyridine (314) in 10% yield (Scheme 163). [209] Scheme 163.…”

Section: P(o)h Was Employed As the Prea C H T U N G T R E N N U N G Lmentioning

confidence: 99%

“…[209] They described that treatment of 2-(2-bromophenoxy)pyridine (313) with 10 mol% PdA C H T U N G T R E N N U N G (OAc) 2 in DMA at 170 8C for 48 h in the presence of Na 2 CO 3 as the base gave benzofurano-A C H T U N G T R E N N U N G [2,3-b]pyridine (314) in 10% yield (Scheme 163). [209] Scheme 163. Intramolecular Pd-catalyzed arylation of compound 313.…”

Section: P(o)h Was Employed As the Prea C H T U N G T R E N N U N G Lmentioning

confidence: 99%

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Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

et al. 2014

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In recent years, transition metal-catalyzed direct (hetero)arylation reactions of heteroarenes with (hetero)aryl halides and pseudohalides have received significant attention as eco-friendly and economic alternatives to classical methods for the construction of heteroaryl-(hetero)aryl C À C bonds by transition metal-catalyzed cross-couplings involving the use of stoichiometric amounts of organometallic reagents. This critical review with 430 references covers the results obtained in the period January 2009 to February 2013 in the area of the transition metal-catalyzed direct inter-and intramolecular (hetero)arylation reactions of heteroarenes containing one heteroatom. Particular attention has been given to illustrate chemo-and site selectivity aspects of these reactions as well applications of these C À C bond forming reactions in the synthesis of pharmaceutically relevant compounds, natural products and their analogues and precursors. The most recent advancements into the mechanism(s) of these reactions have also been briefly reported.

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Section: P(o)h Was Employed As the Prea C H T U N G T R E N N U N G Lmentioning

confidence: 99%

Section: P(o)h Was Employed As the Prea C H T U N G T R E N N U N G Lmentioning

confidence: 99%

Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

et al. 2014

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“…Os pesquisadores Ames e Opalko foram os primeiros a relatar a síntese de 1 por reações de desidro-halogenação de 2-halobenzoilanilinas ou de benzoil-2-haloanilinas catalisadas por paládio (Figura 2, C). 45 A abordagem utilizada é atualmente conhecida como um método de arilação direta 46 (intramolecular) e é um método bastante empregado para a síntese de derivados de fenantridinonas. Os métodos de arilação direta catalisada por sais de paládio aplicados à síntese de 1 tipicamente envolvem a reação de um haloareno (bromo e iodo derivados são Vol.…”

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Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

Costa¹,

Silva²,

Lucas³

et al. 2016

Química Nova

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publicado na web em 18/02/2015 SYNTHESIS OF PHENANTHRIDINONE DERIVATIVES BY DIRECT ARYLATION. CHARACTERIZATION OF THE ABSORPTION AND EMISSION SPECTRA FOR REPRESENTATIVE EXAMPLES. The phenanthridinone heterocyclic system has attracted considerable attention in recent years due to the diverse array of physical, chemical and pharmacological properties demonstrated by natural and synthetic derivatives. As a consequence there has been considerable development of synthetic methodology for the synthesis of this and related heterocyclic ring systems. The synthetic literature is discussed and is compared with a direct arylation methodology for the intramolecular cyclization of tertiary (2-iodo)benzoylamides to generate the biaryl bond of these compounds. The efficient methodology allowed the synthesis of a number of previously unknown phenanthridinone products. The photoluminescent properties of representative examples were characterized and it is proposed that the previously unknown compound 1s reveals dual fluorescence in a manner similar to the known compound 1r.

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“…10 This reaction afforded an unstable alcohol that was readily oxidized using manganese dioxide to generate ketone 13 in 86% yield over two steps, as shown in Scheme 4. An intramolecular Heck reaction 11 on bromo benzophenones 13a-13c cleanly provided azafluorenones 1, 2, and 3 in 53%, 47%, and 50% yields, respectively. Natural product 4 was isolated from the stem barks of Oncodostigma monosperma.…”

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Synthesis of Azafluorenone Antimicrobial Agents

Kraus

Kempema

2010

J. Nat. Prod.

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The azafluorenones constitute a growing class of alkaloids. 1 Representative natural products of this class include compounds 1-5 as shown. Onychine (1) was active against C. albicans B311 with a MIC of 3.12 µg per milliliter. 2 In addition, compound 1 also exhibited antimicrobial activity against S. aureus NCTC 8530, B. subtilis IFO 3007, Escherichia coli IFO 3545, and Saccharomyces cereVisiae IFO 0203 in the range 50 to >100 µg per milliliter. 3 Polyfothine (2) shows DNA-damaging activity. 4 Isoursuline (5) exhibited antimalarial activity against Plasmodium falciparum at micromolar concentrations. 5 Both compounds 1 and 2 have been synthesized by Koyama using an acid-catalyzed rearrangement of the oxime O-allyl ether of an indanone. 6 Compound 1 has also been synthesized by way of intramolecular Friedel-Crafts reactions and organometallic coupling reactions. 7,8 Of particular note is the novel boronic acid coupling developed by Snieckus and co-workers. 9

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Palladium-catalysed cyclisation of 2-substituted halogenoarenes by dehydrohalogenation

Cited by 238 publications

References 30 publications

Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

Cross‐Coupling of Heteroarenes by CH Functionalization: Recent Progress towards Direct Arylation and Heteroarylation Reactions Involving Heteroarenes Containing One Heteroatom

Synthesis of Phenanthridinone Derivatives by Direct Arylation. Characterization of the Absorption and Emission Spectra for Representative Examples

Synthesis of Azafluorenone Antimicrobial Agents

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