- A mild synthesis of substituted 1,8-naphthyridines
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A greener method for the synthesis of substituted 1,8-naphthyridines has been developed, which is supported by reaction metric analysis. Using 2-aminonicotinaldehyde as a starting material with a variety of carbonyl reaction partners, the Friedl?nder reac
- Anderson, Edward C.,Sneddon, Helen F.,Hayes, Christopher J.
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Read Online
- Synthesis of 1,8-naphthyridine and BF2-based isomers and their application in fluorogenic sensing Cd2+
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A series of isomers were synthesized and identified, two isomers of which were developed as the dual-channel fluorescent probe toward Cd2+. BF2 dissociates from the probe upon reaction with CdCl2, demonstrating a new approach for sensing Cd2+.
- Liu, Xingjiang,Chen, Mingxing,Liu, Ziping,Yu, Mingming,Wei, Liuhe,Li, Zhanxian
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Read Online
- Olefin oxygenation by water on an iridium center
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Oxygenation of 1,5-cyclooctadiene (COD) is achieved on an iridium center using water as a reagent. A hydrogen-bonding interaction with an unbound nitrogen atom of the naphthyridine-based ligand architecture promotes nucleophilic attack of water to the met
- Ghatak, Tapas,Sarkar, Mithun,Dinda, Shrabani,Dutta, Indranil,Rahaman, S. M. Wahidur,Bera, Jitendra K.
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Read Online
- High-selectivity fibroblast growth factor receptor inhibitor and application
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The invention discloses a high-selectivity fibroblast growth factor receptor inhibitor and application, and particularly relates to a compound shown in a formula (I) or a pharmaceutically acceptable salt, a solvate, a geometric isomer, a stereoisomer, a tautomer and any mixture thereof. The compound shown in the formula (I) or the pharmaceutically acceptable salt, the solvate and the pharmaceutical composition thereof can be applied to prevention or treatment of diseases related to FGFR4 activity or overexpression, and can also be combined with other medicines to be used for treating various related diseases, especially for treating various cancers, wherein the cancers may be liver cancer, lung cancer, gastric cancer, breast cancer, ovarian cancer, prostate cancer, renal cell carcinoma, skin cancer, colon cancer, bile duct cancer, glioma or sarcoma.
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Paragraph 0087-0091
(2021/07/08)
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- ALPHAvBETA1 INTEGRIN ANTAGONISTS
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The present disclosure provides pharmaceutical agents, including those of the formula: (I) wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such pharmaceutical agents. Methods of using the pharmaceutical agents are also provided. The compounds may be used for the inhibition or antagonism of integrins ανβ1 and/or α5β1. In some embodiments, the compounds provided herein exhibit reduced inhibitory or antagonistic activity of integrins ανβ3, ανβ5, ανβ6, ανβ8, and/or αIIbβ3.
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Paragraph 0173
(2020/01/31)
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- Cooperative H2 Activation on Dicopper(I) Facilitated by Reversible Dearomatization of an “Expanded PNNP Pincer” Ligand
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A naphthyridine-derived expanded pincer ligand is described that can host two copper(I) centers. The proton-responsive ligand can undergo reversible partial and full dearomatization of the naphthyridine core, which enables cooperative activation of H2 giving an unusual butterfly-shaped Cu4H2 complex.
- Kounalis, Errikos,Lutz, Martin,Broere, Dani?l L. J.
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supporting information
p. 13280 - 13284
(2019/10/28)
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- PYRROLOPYRAZINE DERIVATIVES AS ALPHA V INTEGRIN INHIBITORS
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The disclosure relates to compounds of formula I: Formula I which inhibit αv-containing integrins, and includes pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with dysregulation of αV-containing integrins, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders.
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Page/Page column 39
(2019/05/30)
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- Transition metal-free α-methylation of 1,8-naphthyridine derivatives using DMSO as methylation reagent
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A practical approach to the direct α-methylation of 1,8-naphthyridines under mild reaction conditions has been developed using simple and readily available DMSO as a convenient and environmentally friendly carbon source. This method is transition metal-free and highly chemoselective, shows good functional group tolerance, and uses DMSO as a methyl source, providing efficient and rapid access to an important compound class, 2-methyl-1,8-naphthyridines.
- Jiang, Shaohua,Yang, Zhihai,Guo, Ziyin,Li, Yibiao,Chen, Lu,Zhu, Zhongzhi,Chen, Xiuwen
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p. 7416 - 7424
(2019/08/15)
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- Diruthenium complexes with a 1,8-Naphthyridine-based Bis(silyl) supporting ligand: Synthesis and structures of complexes containing RuII2(μ-H)2 and RuI2 cores
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We designed a novel naphthyridine-based supporting ligand involving two silyl coordinating moieties at 2,7-positions, t-BuNBSi, for the synthesis of dinuclear metal complexes. Reaction of a ligand precursor t-BuNBSi(H)2 (1) with Ru3(CO)12 gave a di-μ-hydridodiruthenium(II,II) complex (t-BuNBSi)Ru2(μ-H)2(CO)4 (2). Photoirradiation to 2 resulted in the formation of a diruthenium(I,I) complex (t-BuNBSi)Ru2(CO)6 (3). The SiRuRuSi linkage of 2 takes a zigzag arrangement, whereas that of 3 adopts a roughly linear one.
- Kusuma, Indra,Komuro, Takashi,Tobita, Hiromi
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p. 400 - 403
(2018/03/27)
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- INTEGRIN ANTAGONISTS
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The present disclosure provides pharmaceutical agents, including those of the formula:(I) wherein the variables are defined herein. Also provided are pharmaceutical compositions, kits and articles of manufacture comprising such pharmaceutical agents. Meth
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Page/Page column 57
(2018/08/03)
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- A four-hydrogenated 1, 8 - naphthyridine apperception composition preparation method and its prepared chiral products
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The invention discloses a preparation method of a tetrahydro 1, 8-naphthyridine compound. The preparation method comprises the following steps: under the existence of a chiral catalyst, enabling a compound with the structure shown in the formula (1) (in the description) and hydrogen to be subjected to addition reaction, wherein the chiral catalyst is a coordination compound with the structure shown in the formula (2) (in the description). The invention further provides a chiral product of the tetrahydro 1, 8-naphthyridine compound, prepared through the preparation method. According to the invention, the proper compound with the structure shown in the formula (1) (in the description) is used as a substrate, and the proper coordination compound with the structure shown in the formula (2) (in the description) is used as the chiral catalyst to perform selective hydrogenation reduction on 1, 8-naphthyridine compound with the structure shown in the formula (1) by adopting hydrogen, so that the chiral product of the tetrahydro 1, 8-naphthyridine compound is prepared with low cost. The chiral product of the tetrahydro 1, 8-naphthyridine compound can be used as a biologically active compound and a structural building block of a chiral drug.
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Paragraph 0206; 0208
(2018/03/26)
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- PYRROLE AMIDES AS ALPHA V INTEGRIN INHIBITORS
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The present invention provides compounds of Formula (I) or stereoisomers, tautomers, or pharmaceutically acceptable salts or solvates thereof, wherein all the variables are as defined herein. These compounds are inhibitors to αv-containing integrins. This invention also relates to pharmaceutical compositions comprising these compounds and methods of treating a disease, disorder, or condition associated with dysregulation of αv-containing integrins, such as pathological fibrosis, transplant rejection, cancer, osteoporosis, and inflammatory disorders, by using the compounds and pharmaceutical compositions.
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Page/Page column 67
(2018/05/27)
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- Double Dehydrogenation of Primary Amines to Nitriles by a Ruthenium Complex Featuring Pyrazole Functionality
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A ruthenium(II) complex bearing a naphthyridine-functionalized pyrazole ligand catalyzes oxidant-free and acceptorless selective double dehydrogenation of primary amines to nitriles at moderate temperature. The role of the proton-responsive entity on the ligand scaffold is demonstrated by control experiments, including the use of a N-methylated pyrazole analogue. DFT calculations reveal intricate hydride and proton transfers to achieve the overall elimination of 2 equiv of H2.
- Dutta, Indranil,Yadav, Sudhir,Sarbajna, Abir,De, Subhabrata,H?lscher, Markus,Leitner, Walter,Bera, Jitendra K.
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supporting information
p. 8662 - 8666
(2018/07/09)
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- From Anilines to Quinolines: Iodide- and Silver-Mediated Aerobic Double C?H Oxidative Annulation–Aromatization
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Quinoline synthesis from easily accessible raw materials such as anilines is a valuable and meaningful task. Herein, we communicate an iodide- and silver-mediated C?H/C?H oxidative annulation–aromatization between anilines and allyl alcohols. This protocol provides a direct route to the synthesis of quinoline derivatives from inexpensive commodities. Various kinds of anilines, even heterocyclic anilines, were shown to be workable substrates, generating the corresponding multi-substituted quinolines in good yields.
- Wu, Jiwei,Liao, Zhixiong,Liu, Dong,Chiang, Chien-Wei,Li, Zheng,Zhou, Zhonghao,Yi, Hong,Zhang, Xu,Deng, Zixin,Lei, Aiwen
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supporting information
p. 15874 - 15878
(2017/10/23)
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- Highly active palladium catalysts containing a 1,10-phenanthroline analogue N-heterocyclic carbene for room temperature Suzuki-Miyaura coupling reactions of aryl chlorides with arylboronic acids in aqueous media
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Two new palladium (II) complexes containing a 1,10-phenanthroline analogue N-heterocyclic carbene (NHC) have been synthesized. The complexes were characterized by 1H and 13C NMR spectroscopy and elemental analysis and their structures were determined by single-crystal X-ray diffraction. The NHC-palladium complexes were employed as catalysts for Suzuki-Miyaura coupling reactions of aryl chlorides with arylboronic acids in aqueous media at room temperature. The cross-coupling reactions were highly efficient with low catalysts loadings.
- Liu, Guiyan,Liu, Chengxin,Han, Fangwai,Wang, Zhongliang,Wang, Jianhui
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supporting information
p. 726 - 731
(2017/03/31)
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- GLYCOSIDASE INHIBITORS
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Compounds of formula (I) wherein A, R, W, Q, n and m have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.
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Page/Page column 118; 119
(2017/09/15)
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- GLYCOSIDASE INHIBITORS
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Compounds of formula (I) wherein A, R, W, Q, n and m have the meaning according to the claims can be employed, inter alia, for the treatment of tauopathies and Alzheimer's disease.
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Page/Page column 102-103
(2017/09/15)
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- Selective synthesis of nitrogen bi-heteroarenes by a hydrogen transfer-mediated direct α,β-coupling reaction
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By an external hydrogen transfer-mediated activation mode, we herein demonstrate a new palladium-catalyzed direct α,β-coupling of different types of N-heteroarenes. Such a selective coupling reaction proceeds with the advantages of operational simplicity,
- Chen, Xiu-Wen,Zhao, He,Xiong, Biao,Jiang, Huan-Feng,Dixneuf, Pierre. H.,Zhang, Min
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supporting information
p. 6093 - 6097
(2017/08/02)
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- Method for preparing 1,8-naphthyridine and derivatives
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The invention provides a method for preparing 1,8-naphthyridine and derivatives. The method comprises the following steps of adding an oxidizing agent and a compound in formula (I) or salt thereof into acid, so as to obtain a reaction liquid; stirring and heating the reaction liquid, uniformly dripping a compound in formula (II) to react, cooling to the room temperature, neutralizing by an alkaline solution, and extracting a water phase by solvent, so as to obtain an organic phase; concentrating the organic phase under reduced pressure, and removing the solvent, so as to obtain a compound in formula (III). The method overcomes the defects of low yield and high cost when the 1,8-naphthyridine and derivatives are synthesized by a Skraup method.
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Paragraph 0029-0031
(2018/02/04)
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- 2-(2'-hydroxyl styryl) naphthyridine probe reagent and preparation and application thereof
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The invention discloses a 2-(2'-hydroxyl styryl) naphthyridine probe reagent and preparation and application thereof. The probe reagent is mainly prepared by concentrated sulfuric acid, sodium 3-nitrobenzene sulfonate, boric acid, FeSO4.7H2O, 2-amino-6-picoline, salicylide, glycerol and acetic anhydride. The 2-(2'-hydroxyl styryl) naphthyridine probe reagent has the advantages that the probe reagent can selectively detect various target ions, single-probe, multi-target and multi-mode identification and detection are achieved, and the probe reagent can be used for detecting Hg, Ag and F ions; a probe is simple in structure, low in preparation cost, diversified in detection and identification manners, high in detection sensitivity, good in selectivity, excellent in performance, easy in operation condition control and promising in application prospect.
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Paragraph 0109; 0110; 0111; 0112
(2017/05/02)
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- Synthesis of quinolines and naphthyridines: Via catalytic retro-aldol reaction of β-hydroxyketones with ortho -aminobenzaldehydes or nicotinaldehydes
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A Cu(i)-catalyzed retro-aldol reaction of β-hydroxyketones with ortho-aminobenzaldehydes and nicotinaldehydes is reported that produces a range of quinolines and naphthyridines with high efficiency and selectivity. This reaction uses β-hydroxyketones as a regiospecific ketone-protected enolate source via copper-catalyzed retro-aldol Cα-Cβ bond cleavage. The in situ generated copper enolate undergoes kinetically favorable cyclization with ortho-amino aryl aldehydes to produce quinolines and naphthyridines in a chemo- and regioselective manner. The mild and weakly basic reaction conditions also suppress possible side reactions of benzaldehydes under strongly basic conditions, resulting in improved reaction yields.
- Zhang, Song-Lin,Deng, Zhu-Qin
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supporting information
p. 8966 - 8970
(2016/10/05)
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- Borane-catalyzed metal-free hydrogenation of 2,7-disubstituted 1,8-naphthyridines
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Metal-free hydrogenation of 2,7-disubstituted 1,8-naphthyridines was successfully realized for the first time using in situ generated borane catalysts under mild conditions to furnish 1,2,3,4-tetrahydro-1,8-naphthyridine derivatives in 83-98% yields. Significantly, up to 74% ee was achieved for the corresponding asymmetric hydrogenation reactions.
- Wang, Wei,Feng, Xiangqing,Du, Haifeng
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supporting information
p. 6683 - 6686
(2016/07/21)
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- Ruthenium-Catalyzed Enantioselective Hydrogenation of 1,8-Naphthyridine Derivatives
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The first asymmetric hydrogenation of 2,7-disubstituted 1,8-naphthyridines catalyzed by chiral cationic ruthenium diamine complexes has been developed. A wide range of 1,8-naphthyridine derivatives were effectively hydrogenated to give 1,2,3,4-tetrahydro-1,8-naphthyridines with up to 99% ee and full conversions. The method provides a practical and facile approach to the preparation of valuable chiral heterocyclic building blocks and useful motifs for a new kind of P,N-ligand.
- Ma, Wenpeng,Chen, Fei,Liu, Youran,He, Yan-Mei,Fan, Qing-Hua
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p. 2730 - 2733
(2016/06/15)
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- Copper-catalyzed retro-aldol reaction of β-hydroxy ketones or nitriles with aldehydes: Chemo- and stereoselective access to (E)-enones and (E)-acrylonitriles
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A copper-catalyzed transfer aldol type reaction of β-hydroxy ketones or nitriles with aldehydes is reported, which enables chemo- and stereoselective access to (E)-α,β-unsaturated ketones and (E)-acrylonitriles. A key step of the in situ copper(i)-promoted retro-aldol reaction of β-hydroxy ketones or nitriles is proposed to generate a reactive Cu(i) enolate or cyanomethyl intermediate, which undergoes ensuing aldol condensation with aldehydes to deliver the products. This reaction uses 1.2 mol% Cu(IPr)Cl (IPr denotes 1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene) as the catalyst in the presence of 6.0 mol% NaOtBu cocatalyst at room temperature or 70 °C. A range of aryl and heteroaryl aldehydes as well as acrylaldehydes are compatible with many useful functional groups being tolerated. Under the mild and weakly basic conditions, competitive Cannizzaro-type reaction of benzaldehydes and side reactions of base-sensitive functional groups can be effectively suppressed, which show synthetic advantages of this reaction compared to classic aldol reactions. The synthetic potential of this reaction is further demonstrated by the one-step synthesis of biologically active quinolines and 1,8-naphthyridine in excellent yields (up to 91%). Finally, a full catalytic cycle for this reaction has been constructed using DFT computational studies in the context of a retro-aldol/aldol two-stage mechanism. A rather flat reaction energy profile is found indicating that both stages are kinetically facile, which is consistent with the mild reaction conditions.
- Zhang, Song-Lin,Deng, Zhu-Qin
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p. 7282 - 7294
(2016/08/05)
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- TRIAZOLO-PYRAZINE DERIVATIVES USEFUL IN THE TREATMENT OF DISORDERS OF THE CENTRAL NERVOUS SYSTEM
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Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes.
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Paragraph 00227
(2014/06/23)
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- Fluorinated 3-(2-Oxo-3-(3-Arylpropyl)Imidazolidin-1-yl)-3-Arylpropanoic Acid Derivatives
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The invention relates to fluorinated compounds and their use as integrin receptor antagonists. Novel fluorinated 3-(2-oxo-3-(3-arylpropyl)imidazolidin-1-yl)-3-arylpropanoic acid derivatives and pharmaceutically acceptable salts or solvates thereof and their use are described.
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Paragraph 0360
(2014/08/19)
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- HETEROARYL COMPOUNDS AND METHODS OF USE THEREOF
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Provided herein are heteroaryl compounds, methods of their synthesis, pharmaceutical compositions comprising the compounds, and methods of their use. In one embodiment, the compounds provided herein are useful for the treatment, prevention, and/or management of various disorders, such as CNS disorders and metabolic disorders, including, but not limited to, e.g., neurological disorders, psychosis, schizophrenia, obesity, and diabetes
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Page/Page column 127
(2011/12/14)
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- Palladium-catalyzed benzylic arylation of 2-methyl azaarenes
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A palladium-catalyzed benzylic sp3 direct arylation of electron-deficient heterocycles is reported. The method described enables the introduction of electron-rich and -poor aromatics at the benzylic position of heterocycles without the need for
- Burton, Paul M.,Morris, James A.
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body text
p. 5359 - 5361
(2011/02/25)
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- A one-pot method for the synthesis of naphthyridines via modified friedl?nder reaction
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A one-pot method for the preparation of 1,8-naphthyridine derivatives is reported. The method involves the dimetalation of an appropriate N-2-pyridylpivalamide or tert-butylcarbamate followed by reaction with a β-dimethylamino or β-alkoxyacrolein derivative. This method is also applicable to 1,6-naphthyridines. Georg Thieme Verlag Stuttgart.
- Zhichkin, Pavel,Beer, Catherine M. Cillo,Rennells, W. Martin,Fairfax, David J.
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p. 379 - 382
(2007/10/03)
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- Synthesis of pyrazoles and isoxazoles as potent αvβ3 receptor antagonists
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We describe a series of pyrazole and isoxazole analogs as antagonists of the αvβ3 receptor. Compounds showed low to sub-nanomolar potency against αvβ3, as well as good selectivity against αIIbβ3
- Penning, Thomas D.,Khilevich, Albert,Chen, Barbara B.,Russell, Mark A.,Boys, Mark L.,Wang, Yaping,Duffin, Tiffany,Engleman, V. Wayne,Finn, Mary Beth,Freeman, Sandra K.,Hanneke, Melanie L.,Keene, Jeffery L.,Klover, Jon A.,Nickols, G. Allen,Nickols, Maureen A.,Rader, Randall K.,Settle, Steven L.,Shannon, Kristen E.,Steininger, Christina N.,Westlin, Marisa M.,Westlin, William F.
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p. 3156 - 3161
(2007/10/03)
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- Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- Non-peptidic αvβ3 antagonists containing indol-1-yl propionic acids
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We describe the synthesis and structure/activity relationship of RGD mimetics that are potent inhibitors of the integrin αvβ 3. Indol-1-yl propionic acids containing a variety of basic moieties at the 5-position, as well as substitutions alpha and beta to the carboxy terminus were synthesized and evaluated. Novel compounds with improved potency have been identified.
- Leonard, Kristi,Pan, Wenxi,Anaclerio, Beth,Gushue, Joan M.,Guo, Zihong,DesJarlais, Renee L.,Chaikin, Marge A.,Lattanze, Jennifer,Crysler, Carl,Manthey, Carl L.,Tomczuk, Bruce E.,Marugan, Juan Jose
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p. 2679 - 2684
(2007/10/03)
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- Friedlaender reactions of triacetylmethane- unusual distribution of products-
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Friedlaender reactions of triacetylmethane with selected β-amino-α,β-unsaturated aldehydes afforded pyridoheterocycles and their 2-methyl derivatives instead of triheteroarylmethane.
- Rahman, A.F.M. Motiur,Kwon, Youngjoo,Jahng, Yurngdong
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p. 2777 - 2782
(2007/10/03)
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- NOVEL PROCESSES FOR THE SYNTHESIS OF CYCLOPROPYL COMPOUNDS
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This invention relates to processes for the preparation of cyclopropyl compounds of Formula: (I) wherein: x is an integer selected from the group consisting of 0, 1 and 2; R and R are independently selected from the group consisting of H, C1-C6 alkyl, and halo; and R, R, R, R and R are independently selected from the group consisting of H, C1-C6 alkyl, C1-C6 alkoxy, and halo.
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Page/Page column 29
(2010/02/11)
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- VITRONECTIN RECEPTOR ANTAGONISTS
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Compounds of formula (I) are disclosed which are vitronectin receptor antagonists and are useful in the treatment of osteoporosis wherein R is Het- or Ar; R is formula (a) or formula (b); or a pharmaceutically acceptable salt thereof.
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- PYRAZOLE COMPOUNDS AS INTEGRIN RECEPTOR ANTAGONISTS DERIVATIVES
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The present invention relates to pharmaceutical compositions comprising compounds of the Formula (I), and methods of selectively inhibiting or antagonizing the αVβ3 and/or the α Vβ5 integrin without significantly inhibitin
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- Cycloalkyl alkanoic acids as integrin receptor antagonists derivatives
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- Bicyclic alphavbeta3 antagonists
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αvβ3 and/or αvβ5 integrin.
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- Cycloalkyl alkanoic acids as integrin receptor antagonists
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The present invention relates to a class of compounds represented by the Formula I or a pharmaceutically acceptable salt thereof, pharmaceutical compositions comprising compounds of the Formula I, and methods of selectively inhibiting or antagonizing the αVβ3 and/or αVβ5 integrin.
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- A Search for Lone-Pair Interactions in Forward and Reverse Menschutkin Reactions of Some Diaza Heterocycles
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The rates of methylation (forward reaction) of phthalazine (1), 1,8-naphthyridine (2), 1,10-phenanthroline (3), and of some ring methyl derivatives are compared with the rates of demethylation of the corresponding N-methyl quaternary iodides.It was observed for (2), and especially for (3), that a nitrogen lone pair in place of a CH group (quinoline and 8-methylquinoline, respectively) aids the forward reaction but does not have a commensurate retarding effect on the reverse process.In contrast to (3), 2,2'-bipyridine showed behaviour typical of α-substituted pyridines.The introduction of a 2-methyl group into (3) had an appreciable rate-enhancing effect on methylation (at N 10) and this is interpreted as evidence for lone-pair cooperativity in the forward reaction
- Deady, Leslie W.
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p. 163 - 170
(2007/10/02)
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