Kinetics of the Decarboxylative Elimination of Cinnamic Acid Dibromides

Trumbull, Elmer R.; Finn, Richard T.; Ibne‐Rasa, Khairat M.; Sauers, Carol K.

doi:10.1021/jo01054a012

Cited by 25 publications

(15 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For example, the 3-nitro-, 3-amino-, and 3-hydroxyquinolines 7a, 8a, and 9a were inactive. We also tested the parent 6,7-dimethoxyquinoline25 (21) and found it to lack inhibitory activity. When 8a or 9a were benzylated (i.e., compounds 19 and 20), activity was restored such that <100 nM IC50 values were obtained.…”

Section: Resultsmentioning

confidence: 99%

A New Series of PDGF Receptor Tyrosine Kinase Inhibitors: 3-Substituted Quinoline Derivatives

Maguire¹,

Sheets²,

McVety³

et al. 1994

J. Med. Chem.

429

197

View full text Add to dashboard Cite

A series of 63 3-substituted quinoline derivatives has been prepared and tested for inhibition of cell-free platelet derived growth factor receptor tyrosine kinase (PDGF-RTK) activity. The compounds were generally prepared either by a Friedlander condensation between an aryl-acetaldehyde and an o-aminobenzaldehyde or by a palladium-catalyzed coupling between an aryl bromide or triflate and an organostannane or organozinc chloride. The presence of 6,7-dimethoxy groups on the quinoline ring was found to be advantageous although not essential for potent inhibition of PDGF-RTK. A lipophilic group attached to the quinoline 3-position contributed substantially to activity. The lipophilic groups generally consisted of monocyclic aromatics or small alkynyl, alkenyl, and alkyl groups. Optimum activity of ca. < or = 20 nM (IC50) was observed when 6,7-dimethoxyquinoline was substituted in the 3-position with 4-methoxyphenyl (15d), 3-fluoro-4-methoxyphenyl (17m), 3-fluorophenyl (17b), 4-hydroxyphenyl (24), 6-methoxypyridin-3-yl (15o), 5-pyridin-2(1H)-one (23), trans-beta-styryl (15e), thiophene-3-yl (2e), 5-chlorothiophene-2-yl (15f), or cyclopentenyl (17n) groups. Most of the compounds in the series were tested for inhibition of cell-free epidermal growth factor receptor tyrosine kinase activity and found to be inactive.

show abstract

Section: Resultsmentioning

confidence: 99%

A New Series of PDGF Receptor Tyrosine Kinase Inhibitors: 3-Substituted Quinoline Derivatives

Maguire¹,

Sheets²,

McVety³

et al. 1994

J. Med. Chem.

429

197

View full text Add to dashboard Cite

show abstract

“…No evidence could be found for two primary processes. 22 Earlier, Trumbull and co-workers found that electron-withdrawing groups in 7b led to formation of cis-4, particularly in solvents of low ionizing power, whereas electron-donating groups X led to formation of the more stable trans-4.22 These results were interpreted in terms of a dual mechanism originally proposed by Cristol and Norris (i.e., mostly El for X = p -CH3O and mostly E2 for X = P-NO2). 14 Bordwell and Knipe interpreted these results in terms of an El process in which electrostatic participation by carboxylate was tight or loose (permitting internal rotation) depending on X and solvent.…”

mentioning

confidence: 99%

Substituent effects on bromodecarboxylation reactions

Kingsbury¹,

Max²

1978

J. Org. Chem.

View full text Add to dashboard Cite

“…Unless otherwise noted, reagents were from commercial suppliers. The following compounds were made by the literature procedures: Pt(dppf)Cl 2, p -MeOC 6 H 4 CH=CHBr, [Pt 2 (dppf) 2 H 3 ][BF 4 ] …”

Section: Methodsmentioning

confidence: 99%

Synthesis and Structure of a Cationic Diplatinum μ-Alkylidene μ-Hydride Complex

Zhuravel¹,

Glueck²,

Liable‐Sands³

et al. 1998

Organometallics

View full text Add to dashboard Cite

The dinuclear μ-alkylidene μ-hydride cation [Pt2(dppf)2(μ-CHCH2Ar)(μ-H)][Br] (2, dppf = Ph2PC5H4FeC5H4PPh2, Ar = p-MeOC6H4) was obtained unexpectedly from reaction of p-methoxybromostyrene (3) with Pt(dppf)Cl2/NaBH4/norbornene and crystallographically characterized. Solutions of the hydride [Pt(dppf)H]2 (7), prepared by deprotonation of the known cation [Pt2(dppf)2H3]+ (6) or by treatment of Pt(dppf)Cl2 with two equiv of LiBEt3H, deposit an insoluble precipitate formulated as [Pt(dppf)H] n (11), which also gives 2 on treatment with 3.

show abstract

Kinetics of the Decarboxylative Elimination of Cinnamic Acid Dibromides

Cited by 25 publications

References 0 publications

A New Series of PDGF Receptor Tyrosine Kinase Inhibitors: 3-Substituted Quinoline Derivatives

A New Series of PDGF Receptor Tyrosine Kinase Inhibitors: 3-Substituted Quinoline Derivatives

Substituent effects on bromodecarboxylation reactions

Synthesis and Structure of a Cationic Diplatinum μ-Alkylidene μ-Hydride Complex

Contact Info

Product

Resources

About