19006-63-4Relevant articles and documents
Mild and Regioselective N-Alkylation of 2-Pyridones in Water
Hao, Xin,Xu, Zhongmiao,Lu, Hongfu,Dai, Xuedong,Yang, Ting,Lin, Xichen,Ren, Feng
supporting information, p. 3382 - 3385 (2015/07/28)
A mild and regioselective N-alkylation reaction of 2-pyridones in water has been developed. Tween 20 (2% w/w) was added to create a micellar system for improved solubility of starting materials, which leads to enhanced reaction rates. The protocol demonstrated a wide substrate scope with good isolated yields (40-94%) for all of the 24 examples evaluated. High regioselectivity favoring N-alkylation over O-alkylation was observed for benzyl halides (>5:1), primary alkyl halides (>6:1), and bulky and less reactive secondary alkyl halides (>2.4:1).
Iron-catalyzed regioselective direct arylation at the C-3 position of N-alkyl-2-pyridone
Modak, Atanu,Rana, Sujoy,Maiti, Debabrata
, p. 296 - 303 (2016/09/09)
A number of pharmaceutical compounds possess an arylated 2-pyridone moiety. The existing reports using expensive starting materials and/or superstoichiometric metal salts have prompted us to explore a possible user-friendly method for their synthesis. In this report, we demonstrate an easy-to-handle reaction condition with an iron catalyst for the exclusive generation of C-3-arylated pyridone via C-H functionalization.
Homosecoiridoid alkaloids with amino acid units from the flower buds of lonicera japonica
Yu, Yang,Zhu, Chenggen,Wang, Sujuan,Song, Weixia,Yang, Yongchun,Shi, Jiangong
, p. 2226 - 2233 (2014/01/17)
Nine new homosecoiridoid alkaloids, named lonijaposides O-W (1-9), along with 19 known compounds, were isolated from an aqueous extract of the flower buds of Lonicera japonica. Their structures and absolute configurations were determined by spectroscopic data analysis and chemical methods. Lonijaposides O-W have structural features that involve amino acid units sharing the N atom with a pyridinium (1-5) or nicotinic acid (6-9) moiety. The absolute configurations of the amino acid units were determined by oxidation of each pyridinium ring moiety with potassium ferricyanide, hydrolysis of the oxidation product, and Marfey's analysis of the hydrolysate. This procedure was validated by oxidizing and hydrolyzing synthetic model compounds. The phenylalanine units in compounds 4, 5, and 9 have the d-configuration, and the other amino acid units in 1-3 and 6-8 possess the l-configuration. Compounds 1, 4, 6, and 9 and the known compounds 3,4-di-O-caffeoylquinic acid, 3,5-di-O-caffeoylquinic acid, and 5′-O-methyladenosine exhibited antiviral activity against the influenza virus A/Hanfang/359/95 (H3N2) with IC50 values of 3.4-11.6 μM, and 4 inhibited Coxsackie virus B3 replication with an IC50 value of 12.3 μM.
Microwave assisted rapid preparation of N-alkyl-2-pyridones under neutral conditions by Hilbert-Johnson reaction
Iida, Hirokazu,Suda, Machiko,Nakajima, Etsuko,Hakamatsuka, Hiroko,Nagashima, Yuka,Joho, Kouta,Amemiya, Kenta,Moromizato, Tatsuya,Matsumoto, Kiyoshi,Murakami, Yasuoki,Hamana, Hiroshi
scheme or table, p. 2057 - 2062 (2011/04/12)
The reactions of 2-methoxypyridine with haloalkanes without solvent and catalyst under microwave irradiation (100-200 °C, 5 min) yielded the corresponding N-alkyl-2(1H)-pyridones in good to moderate yields. However, the reactions were sensitive to length of haloalkanes. In contrast, the reactions of 2-alkoxypyridines with corresponding iodoalkanes under microwave irradiation (150 °C) proceeded rapidly without catalyst and solvent, and were complete within 5 min to afford N-alkyl-2(1H)-pyridones in good to excellent yields. The Japan Institute of Heterocyclic Chemistry.
Value of zeolites in asymmetric induction during photocyclization of pyridones, cyclohexadienones and naphthalenones
Sivasubramanian, Karthikeyan,Kaanumalle, Lakshmi S.,Uppili, Sundararajan,Ramamurthy
, p. 1569 - 1576 (2008/02/05)
Two strategies, namely chiral inductor and chiral auxiliary approaches, have been examined within zeolites with the aim of achieving asymmetric induction during the photocyclization of cyclohexadienone, naphthalenone and pyridone derivatives. Within zeoli
Intermolecular Photoaddition Reaction of Aliphatic tert-Amines to N-Alkyl-2-pyridones
Ohmiya, Shigeru,Noguchi, Masayo,Chen, Chin-Yuen,Murakoshi, Isamu,Otomasu, Hirotaka
, p. 2516 - 2518 (2007/10/02)
N-Alkyl-2-pyridones reacted on irradiation with aliphatic tert-amines, such as triethylamine and N-methylpiperidine, by way of addition of an α-C-H-bond of the amines to the pyridone nucleus, yielding 4-substituted 3,4-dihydropyridin-2(1H)-ones (4, 5 and 10) and 6-substituted 3,6-dihydropyridin-2(1H)-ones (3 and 9).Keywords - intermolecular photoaddition; N-alkyl-2-pyridone; aliphatic tert-amine; 3,4-dihydropyridin-2(1H)-one; 3,6-dihydropyridin-2(1H)-one