Halogenation with Copper(II). I. Saturated Ketones and Phenol

Kosower, Edward M.; Cole, Wayne; Guo-juan, WU; Cardy, D. E.; Meisters, George

doi:10.1021/jo01038a007

Cited by 96 publications

(26 citation statements)

References 2 publications

(3 reference statements)

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“…Methyl ethyl ketone 3 3 yielded 3-chlorobutanone 34 (Scheme 13), while methyl cyclopropyl ketone afforded both chloromethyl and dichloromethyl cyclopropyl ketone. When R = Ph, the reaction led tochloropropiophenone [31].…”

Section: Dmfmentioning

confidence: 99%

Versatile Reactivity and Catalytic Effects of Copper(II) Halides in Organic Syntheses

Csende¹,

Stájer

2005

COC

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Copper(II) salts are widely applied for the halogenation of aromatic and heteroaromatic systems, the halides. In coupling reactions, CuCl 2 has been used as a catalyst for the benzylation of aromates, the synthesis of alkanes, and the preparation of diacetylenes, cyclohexenones and symmetric biaryls. It has further proved suitable for stereoselective cyclization to lactones, carbon-nitrogen coupling and lactamization, and for the simple preparation of aroylaminohydrazones, the allylic amination of olefins, the carbonylation of alkylamines, and heterocyclizations to pyrrolidinones, pyridinones, pyrroles and dihydrofurans. The dehydrogenation of carbocycles and heterocycles can be used in the synthesis of gibberelic acid, for the aromatization of oestrogen derivatives and for the conversion of dihydrouracils to uracils. From tetrahydroisoquinolines, dihydro derivatives have been formed, while dihydropyridazines in the presence of Cu(II) salts yield pyridazines. Similarly, the oxidations of cyclohexane, adamantane and methylcatechol to benzoquinone, and amines to nitriles have been performed. The conversion of aldehydes to nitriles and benzyl radical cyclizations to butyrolactones have been achieved. Protection and deprotection, and various other Cu(II) halide-mediated reactions are also discussed.

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Section: Dmfmentioning

confidence: 99%

Versatile Reactivity and Catalytic Effects of Copper(II) Halides in Organic Syntheses

Csende¹,

Stájer

2005

COC

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“…In order to effect the bromination of XVII, an alternate method was utilized which gave ample quantities of bromoketone XX (32). The corresponding chloride derivatives (XXI and XXII) of XV and XVI were prepared by reaction with copper chloride and lithium chloride in N,N-dimethylformamide (33). The assignments of the α -configuration to the halogen atoms at C (6) were verified using known coupling constants from the Si NMR spectra which are correlated to the x-ray structure determination of XVIII (16,34-37)· In Scheme 3, the α-bromoketones XVIII and XIX were converted to lactones XXIII and XXIV by refluxing in collidine (4, 16,38).…”

Section: Chemical Synthesis Of Podocarpic Acid Derivativesmentioning

confidence: 99%

Synthesis and Fungistatic Activity of Podocarpic Acid Derivatives

Parish

Bradford

Geisler

et al. 1987

ACS Symposium Series

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As a class, octahydrophenanthrene lactones, podolactones, and related podocarpic acid derivatives have been reported to possess a wide variety of biological activities, including antileukemic activity, inhibition of plant cell growth, insect toxicity and antifungal properties. In the present study, a series of synthetic derivatives of podocarpic acid have been prepared by chemical synthesis and evaluated with respect to their ability to inhibit fungal growth. These compounds were evaluated against the Oomycetes-Phytophthora cactorum , Saprolesnia ferax, and Achlya bisexualis and the Ascomycetes-Gibberella fujikuroi. The results of these studies indicate that several of these new synthetic derivatives possess significant antifungal properties.

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“…Recently, various methods have been reported using NBS–NH 4 Oac, NBS‐photochemical, NBS–PTSA, NBS–silica supported sodium hydrogen sulfate, NBS–Amberlyst‐15, NBS–Lewis acids, NBS–ionic liquids, MgBr 2 ‐(hydroxy(tosyloxy)iodo) benzene‐MW[18], N‐methylpyrrolidin‐2‐one hydrotribromide (MPHT), (CH 3 ) 3 SiBr–KNO 3 , DMS, NaBr . Similarly, the α–monochlorination of ketones can be achieved by the reaction of aryl ketones with reagents like sulfuryl chloride, cupric chloride, and benzyltrimethylammoniumdichloroiodate …”

Section: Introductionmentioning

confidence: 99%

Microwave‐Assisted Nanocatalysed Synthesis of Phenacyl Halides as Future Anti‐Platelet Agents

et al. 2019

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An efficient, environmentally benign and novel method for the synthesis of phenacyl halides as antiplatelet agents has been reported in the presence of nanocatalyst (TiO2) by using N‐halosuccinimides (NXS, X=Cl, Br) as a source of halogen and tert‐Butyl Hydrogen Peroxide (TBHP) under microwave irradiation. Compound 2a showed best in vitro antiplatelet activity with 540 and 480 sec as clotting time in prothrombin time (PT) and activated partial thromboplastin time (APTT) assay respectively. Rest compounds showed good to moderate activity. Structures of all synthesized compounds were elucidated by IR, NMR and Mass spectrometry.

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Halogenation with Copper(II). I. Saturated Ketones and Phenol

Cited by 96 publications

References 2 publications

Versatile Reactivity and Catalytic Effects of Copper(II) Halides in Organic Syntheses

Versatile Reactivity and Catalytic Effects of Copper(II) Halides in Organic Syntheses

Synthesis and Fungistatic Activity of Podocarpic Acid Derivatives

Microwave‐Assisted Nanocatalysed Synthesis of Phenacyl Halides as Future Anti‐Platelet Agents

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