Novel nucleophilic substitution of alkyl bromo‐2(1<i>H</i>)‐pyridones

Pessolano, A. A.; Witzel, B. E.; Graham, Peter M.; Clark, Robert L.; Jones, Howard; Dorn, Conrad P.; Carty, Joanne; Shen, T. Y.

doi:10.1002/jhet.5570220205

Cited by 7 publications

(2 citation statements)

References 13 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…After drying under high vacuum, a white solid was obtained (5.25 g, 87%). 1 H NMR (CDCl 3 , 300 MHz) δ 6.32 (s, 1H, Ar-H), 2.45 (s, 3H, 6-Me), 2.27 (s, 3H, 4-Me); 13 C NMR ( d 6 -DMSO, 100 MHz) δ 161.6, 151.0, 144.5, 116.3, 102.2, 23.0, 20.2; mp 255−257 °C (lit . mp 257−259 °C).…”

Section: Methodsmentioning

confidence: 99%

Synthesis and Reactivity of Some 6-Substituted-2,4-dimethyl-3-pyridinols, a Novel Class of Chain-Breaking Antioxidants

et al. 2004

View full text Add to dashboard Cite

The synthesis and study of a series of 6-substituted-2,4-dimethyl-3-pyridinols having interesting antioxidant properties is reported. The general synthetic strategy leading to the compounds involved a low-temperature aryl bromide-to-alcohol conversion as the last step. 2,4-dimethyl-3-pyridinol (1a), 2,4,6-trimethyl-3-pyridinol (1b), and 2,4-dimethyl-6-(dimethylamino)-3-pyridinol (1d) were thus prepared from the corresponding 3-bromopyridine precursor. The methoxy derivative 2,4-dimethyl-6-(methoxy)-3-pyridinol (1c) was also prepared by an alternate route via a Baeyer-Villiger reaction on the substituted benzaldehyde precursor. Novel bicyclic pyridinols 2 and 3 required prior construction of the ring structure. Thus, 2 was prepared by the use of a 6-step intramolecular Friedel-Crafts strategy, and 3 required an 11-step sequence with a thermolytic intramolecular inverse-demand Diels-Alder reaction between a pyrimidine ring and an alkyne as the key step. Basicities of the pyridinols approached physiological pH with increasing electron density in the ring. Pyridinols 1a-d were found to be indefinitely stable to air oxidation while 2 and 3 decomposed upon extended exposure to the atmosphere. The reactivities of the pyridinols toward chain-carrying peroxyl radicals in homogeneous organic solution were examined by studying the kinetics of radical-initiated styrene autoxidations under controlled conditions. These experiments revealed that some of the newly synthesized pyridinols are the most effective phenolic chain-breaking antioxidants reported to date.

show abstract

Section: Methodsmentioning

confidence: 99%

Synthesis and Reactivity of Some 6-Substituted-2,4-dimethyl-3-pyridinols, a Novel Class of Chain-Breaking Antioxidants

et al. 2004

View full text Add to dashboard Cite

show abstract

“…From the exposed free carboxylic acids, a Curtius rearrangement yielded ureas and carbamates. The acid could also be decarboxylated using known procedures …”

Section: Resultsmentioning

confidence: 99%

Simple and Efficient Synthesis of 3,4-Dihydro-2-pyridones via Novel Solid-Supported Aza-Annulation

Wagman¹,

Wang²,

Nuss³

2000

J. Org. Chem.

View full text Add to dashboard Cite

A diverse array of 3,4-dihydro-2-pyridones 13 were produced utilizing the unique properties of solid-supported reactions to both drive the reactions to completion and isolate the desired products. The pyridones were synthesized in high purity by a simple sequence of novel steps commencing from an acetophenone-functionalized resin. The para-substituted acetophenone 9 could be anchored to the resin through either a sulfonamide or a carboxamide linkage. The sulfonamide resin 9a, which gave the best results, was treated with several aryl aldehydes and ethoxide to give a variety of chalcones 10a-k in excellent yield (82-99%) upon TFA cleavage. Addition of either methyl or allyl malonate and DBU to 10a-k afforded smoothly the Michael adducts 11a-j (70-99%) which were subsequently cyclized in one step employing acetic acid as a catalyst and several diverse amines to give pure 3,4-dihydro-2-pyridones 13a-p in moderate to excellent yields (30-98%).

show abstract

Halogenation of Carbonyl and Related Compounds

Larock

Zhang

2018

Comprehensive Organic Transformations

View full text Add to dashboard Cite

Aldehydes and Ketones Acetals Lactols Carboxylic Acids Acid Halides Esters and Lactones Amides and Lactams Imides and Related Compounds Nitriles

show abstract

Novel nucleophilic substitution of alkyl bromo‐2(1H)‐pyridones

Cited by 7 publications

References 13 publications

Synthesis and Reactivity of Some 6-Substituted-2,4-dimethyl-3-pyridinols, a Novel Class of Chain-Breaking Antioxidants

Synthesis and Reactivity of Some 6-Substituted-2,4-dimethyl-3-pyridinols, a Novel Class of Chain-Breaking Antioxidants

Simple and Efficient Synthesis of 3,4-Dihydro-2-pyridones via Novel Solid-Supported Aza-Annulation

Halogenation of Carbonyl and Related Compounds

Contact Info

Product

Resources

About