- Corrigendum: Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles (Chemistry - A European Journal, (2017), 23, 57, (14167-14172), 10.1002/chem.201703642)
-
The authors have been alerted to an error that was unfortunately missed at the time of publication. Table was duplicated with Table 4. The correct version of Table 2 is shown below. The authors apologise for any inconvenience caused. Organo-photoredox catalyzed oxidative dehydrogenation of tetrahydroquinolines (THQ).[a,b] (Table presented.) [a] Reaction conditions: 1 (0.5 mmol), rose bengal (1.0 mol %), N,N-dimethylacetamide (2.0 mL), open air atmosphere under visible-light irradiation at room temperature for 24 h. [b] Isolated yields. [c] 0.1 mol % of photoredox catalyst for 28 h.
- Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
-
-
Read Online
- (Benzo[h])quinolinyl-substituted monoazatriphenylenes: Synthesis and photophysical properties
-
We propose a method for the synthesis of quinolinyl- and benzo[h]quinolinylmonoazatriphenylenes through 1,2,4-triazine intermediates with subsequent transformations in aza-Diels-Alder reaction. The photophysical properties of these new compounds were examined, and the effects due to additional fused aromatic rings were explored.
- Kopchuk,Khasanov,Kovalev,Kim,Nikonov,Zyryanov,Rusinov,Chupakhin
-
-
Read Online
- Structure-function studies on a synthetic guanosine receptor that simultaneously binds Watson-Crick and Hoogsteen sites
-
A series of receptors (11-16) designed to simultaneously bind the Watson-Crick and Hoogsteen sites of guanosine were synthesized, and their binding of guanosine tri-O-pentanoate (32) was probed via 1H NMR complexation studies in 5% DMSO-d6-chloroform-d. The guanosine receptors were synthesized with aminonaphthalene or aminoquinoline auxiliary groups tethered to N-4 of cytosine via a methylene or carbonyl group. A structure-function relationship was established allowing energetic contributions made by components of nucleoside analogues to be probed and more general design rules formulated that may guide the development of more efficacious DNA bases.
- Quinn, Jordan R.,Zimmerman, Steven C.
-
-
Read Online
- Rearrangements of 4-Quinolylcarbene, 3-Quinolylcarbene, and 2-Quinolylcarbene to 1-Naphthylnitrene and Cyanoindenes by Falling Solid Flash Vacuum Pyrolysis
-
The relationship between 4-quinolylcarbene 17, 3-quinolylcarbene 21, 2-quinolylcarbene 25, and 1-naphthylnitrene 35 has been explored experimentally and computationally. The diazomethylquinolines generated from (5-tetrazolyl)quinolines or 1,2,3-triazolo[1,5-a]quinoline by conventional flash vacuum pyrolysis (FVP) were observed by IR spectroscopy. The carbenes were generated by falling solid flash vacuum pyrolysis (FS-FVP). 4-Quinolylcarbene 17 was found to rearrange to 3-quinolylcarbene 21 and then to 2-quinolylcarbene 25, and finally via 1-naphthylnitrene 35 to 1-cyanoindene 36, which then isomerizes to 3- and 2-cyanoindenes 12 and 13. The thermal rearrangement of 2-quinolylcarbene to 1-naphthylnitrene was verified by ESR spectroscopy. The reaction mechanism has been elucidated with the help of calculations of the structures and energies of the quinolylcarbenes and 1-naphthylnitrene and the intervening aza-benzobicyclo[4.1.0]heptatrienes, aza-benzocycloheptatetraenes, and aza-benzocycloheptatrienylidenes and the transition states connecting them at the B3LYP/6-31G? level. The nonobserved 1,2-hydrogen shifts in aza-benzocycloheptatetraenes/aza-benzocycloheptatrienylidenes are found to have very high activation barriers.
- Aylward, Nigel,Kvaskoff, David,Becker, Jürgen,Wentrup, Curt
-
-
Read Online
- One-pot synthesis of nitriles from aldehydes and hydroxylamine hydrochloride over silica gel, montmorillonites K-10, and KSF catalysts in dry media under microwave irradiation
-
A rapid and facile one-pot synthesis of nitriles has been carried out from the corresponding aldehydes and hydroxylamine hydrochloride in the presence of environmentally benign silica gel (84-95%), Mont K-10 (85-96%), and Mont KSF clay (88-98%) catalysts in dry media under microwave irradiation.
- Dewan, Sharwan K.,Singh, Ravinder,Kumar, Anil
-
-
Read Online
- Regioselective direct oxidative C-H cyanation of quinoline and its derivatives catalyzed by vanadium-containing heteropoly acids
-
A direct oxidative C-H cyanation of quinoline and its derivatives using trimethylsilyl cyanide as the cyano source and molecular oxygen as the terminal oxidant has been developed. In the presence of catalytic amounts of vanadium-containing heteropoly acids, e.g., H7PV4Mo8O40, cyanation of various quinoline and its derivatives preferentially took place at the 4-position, affording the corresponding substituted 4-cyanoquinolines as the major products.
- Yamaguchi, Kazuya,Xu, Ning,Jin, Xiongjie,Suzuki, Kosuke,Mizuno, Noritaka
-
-
Read Online
- Triselenium dicyanide (TSD) as a new cyanation reagent: Synthesis of cyano pterins and quinoxalines along with library of cyano N-heterocyclic compounds
-
Triselenium dicynide (TSD) has been reported for the first time to be a novel cyanation reagent for the microwave-assisted one-pot synthesis of a series of various types of cyano N-heterocycles such as pterin, deazapterin, quinoxaline, naphthyridine, and
- Goswami, Shyamaprosad,Maity, Annada C.,Das, Nirmal K.,Sen, Debabrata,Maity, Sibaprasad
-
-
Read Online
- Highly chemoselective deoxygenation of N-heterocyclic: N -oxides under transition metal-free conditions
-
Because their site-selective C-H functionalizations are now considered one of the most useful tools for synthesizing various N-heterocyclic compounds, the highly chemoselective deoxygenation of densely functionalized N-heterocyclic N-oxides has received much attention from the synthetic chemistry community. Here, we provide a protocol for the highly chemoselective deoxygenation of various functionalized N-oxides under visible light-mediated photoredox conditions with Na2-eosin Y as an organophotocatalyst. Mechanistic studies imply that the excited state of the organophotocatalyst is reductively quenched by Hantzsch esters. This operationally simple technique tolerates a wide range of functional groups and allows high-yield, multigram-scale deoxygenation. This journal is
- Kim, Se Hyun,An, Ju Hyeon,Lee, Jun Hee
-
supporting information
p. 3735 - 3742
(2021/05/04)
-
- Metal-Free Deoxygenation of Amine N-Oxides: Synthetic and Mechanistic Studies
-
We report herein an unprecedented combination of light and P(III)/P(V) redox cycling for the efficient deoxygenation of aromatic amine N-oxides. Moreover, we discovered that a large variety of aliphatic amine N-oxides can easily be deoxygenated by using only phenylsilane. These practically simple approaches proceed well under metal-free conditions, tolerate many functionalities and are highly chemoselective. Combined experimental and computational studies enabled a deep understanding of factors controlling the reactivity of both aromatic and aliphatic amine N-oxides.
- Lecroq, William,Schleinitz, Jules,Billoue, Mallaury,Perfetto, Anna,Gaumont, Annie-Claude,Lalevée, Jacques,Ciofini, Ilaria,Grimaud, Laurence,Lakhdar, Sami
-
p. 1237 - 1242
(2021/06/01)
-
- Regioselective Cyanation of Six-Membered N-Heteroaromatic Compounds Under Metal-, Activator-, Base- and Solvent-Free Conditions
-
A regioselective cyanation of heteroaromatic N-oxides with trimethylsilyl cyanide has been developed to obtain 2-substituted N-heteroaromatic nitrile without the requirement of any external activator-, metal-, base-, and solvent. The present protocol is a straightforward, one-pot heteroaromatic C?H cyanation process, and proceeds smoothly in conventional heating but also under microwave irradiation with shorter reaction times. This approach now allows access to a broad class of quinoline N-oxides and other heteroarene N-oxides with high to good yields and can also be scaled up to obtain gram quantities. Further application of this process was observed and utilized in late-stage cyanation of the anti-malarial drug quinine as well as transformation of the 2-cyanoazines to a series of biologically important molecules. Based on the experimental observations, a plausible mechanism has also been proposed highlighting the dual role of trimethylsilyl cyanide as a nitrile source and as an activating agent. (Figure presented.).
- Sarmah, Bikash Kumar,Konwar, Monuranjan,Bhattacharyya, Dipanjan,Adhikari, Priyanka,Das, Animesh
-
supporting information
p. 5616 - 5625
(2019/11/22)
-
- Hypervalent Iodine(III)-Mediated Regioselective Cyanation of Quinoline N-Oxides with Trimethylsilyl Cyanide
-
A regioselective cyanation of quinoline N-oxides with trimethylsilyl cyanide was developed by using (Diacetoxyiodo) benzene (PIDA) as mediated hypervalent iodine(III) reagent under metal-free and base-free reaction conditions to obtain 2-cyanoquinolines. The efficient PIDA reagent could play the role of an activator of the substrates and an accelerator of N?O bond cleavage. The reaction system featured a wide range of substrate suitability and high yields. The procedure was enlarged gram-scale to synthesize the tuberculosis (TB) inhibitor. Finally, according to some experimental results, a plausible mechanism for the cyanation reaction is proposed. (Figure presented.).
- Xu, Feng,Li, Yuqin,Huang, Xin,Fang, Xinjie,Li, Zhuofei,Jiang, Hongshuo,Qiao, Jingyi,Chu, Wenyi,Sun, Zhizhong
-
p. 520 - 525
(2018/12/13)
-
- Cascade Process for Direct Transformation of Aldehydes (RCHO) to Nitriles (RCN) Using Inorganic Reagents NH2OH/Na2CO3/SO2F2 in DMSO
-
A simple, mild, and practical process for direct conversion of aldehydes to nitriles was developed feathering a wide substrate scope and great functional group tolerability (52 examples, over 90% yield in most cases) using inorganic reagents (NH2OH/Na2CO3/SO2F2) in DMSO. This method allows for transformations of readily available, inexpensive, and abundant aldehydes to highly valuable nitriles in a pot, atom, and step-economical manner without transition metals. This protocol will serve as a robust tool for the installation of cyano-moieties to complicated molecules.
- Fang, Wan-Yin,Qin, Hua-Li
-
p. 5803 - 5812
(2019/05/14)
-
- Synthesis method of 2-cyanoquinoline derivative
-
The invention discloses a synthesis method of a 2-cyanoquinoline derivative, and belongs to the technical field of synthesis methods of chinoline and derivatives thereof. The synthesis method includes: adopting a compound represented as in formula (I) and trimethylsilyl cyanide as raw materials, dissolving the raw materials in an organic solvent, catalyzing with H-diethyl phosphite and carbon tetrachloride, and adopting alkali as a deacid reagent to prepare a compound represented as in formula (II). The synthesis method of the 2-cyanoquinoline derivative has the advantages that the adopted catalysts are low in cost and easy to obtain, the raw materials are easy to store, reaction conditions are mild, experimental operations are simple, the obtained 2-cyanoquinoline derivative products are easy to purify, high yield and applicability to industrial production are realized, and a novel synthesis method for preparing the 2-cyanoquinoline derivative is provided.
- -
-
Paragraph 0024-0028
(2019/10/04)
-
- Corresponding amine nitrile and method of manufacturing thereof
-
The invention relates to a manufacturing method of nitrile. Compared with the prior art, the manufacturing method has the characteristics of significantly reduced using amount of an ammonia source, low environmental pressure, low energy consumption, low production cost, high purity and yield of a nitrile product and the like, and nitrile with a more complex structure can be obtained. The invention also relates to a method for manufacturing corresponding amine from nitrile.
- -
-
-
- Dehydration of Amides to Nitriles under Conditions of a Catalytic Appel Reaction
-
A highly expedient protocol for a catalytic Appel-type dehydration of amides to nitriles has been developed that employs oxalyl chloride and triethylamine along with triphenylphosphine oxide as a catalyst. The reactions are usually complete in less than 10 min with only a 1 mol % catalyst loading. The reaction scope includes aromatic, heteroaromatic, and aliphatic amides, including derivatives of α-hydroxy and α-amino acids.
- Shipilovskikh, Sergei A.,Vaganov, Vladimir Yu.,Denisova, Elena I.,Rubtsov, Aleksandr E.,Malkov, Andrei V.
-
supporting information
p. 728 - 731
(2018/02/09)
-
- Quinoline triazole rare-earth compound as well as preparation method and application thereof
-
The invention discloses a quinoline triazole rare-earth compound as well as a preparation method and application thereof. The quinoline triazole rare-earth compound has a structural formula shown as aformula (I) in the description. In the formula (I), the R1 is selected from hydrogen, alkyl, halogenated alkyl or aryl; the Ln is selected from any one kind of materials from yttrium, lanthanum, cerium, praseodymium, neodymium, samarium, europium, gadolinium, terbium, dysprosium, holmium, erbium, thulium, ytterbium and lutecium. Meanwhile, the invention also discloses the preparation method of the quinoline triazole rare-earth compound, and also discloses the application of the quinoline triazole rare-earth compound. Through the preparation of a series of organic ligands simultaneously havingquinoline structures and triazole structures, the rare-earth compound is further prepared; the novel rare-earth compound combining the characteristics of two kinds of structures of quinoline and triazole inherits the characteristics of the two structures in aspects of luminescence property and stability; the goal of improving the performance of the rare-earth organic luminous material is achieved.
- -
-
Paragraph 0075-0077; 0098-0100
(2018/07/30)
-
- Improved Substrate Scope in the Potassium Hexacyanoferrate(II)-Based Cyanation for the Synthesis of Benzonitriles and Their Heterocyclic Analogues
-
The use of Pd(DPEPhos)Cl2 (P26) as a catalyst for the formation of benzonitriles and their heterocyclic analogues provides excellent complementarity to existing catalysts, allowing highly electron-deficient heterocyclic aryl halides to be effic
- Richardson, Jeffery,Mutton, Simon P.
-
p. 4922 - 4931
(2018/05/22)
-
- Preparation method of aromatic nitrile compound or heteroaromatic nitrile compound
-
The invention discloses a preparation method of an aromatic nitrile compound or a heteroaromatic nitrile compound. The preparation method comprises: under the protection of an inert gas, in a solvent,under the actions of a nickel catalyst, a ligand, metal zinc and an additive, carrying out a reaction on a cyanation reagent and halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon. According to the present invention, by using the inexpensive and easily-available nickel catalyst and the ligand, the halogenated aromatic hydrocarbon or halogenated heteroaromatic hydrocarbon,especially the chlorinated aromatic hydrocarbon or chlorinated heteroaromatic hydrocarbon with characteristics of low price, easy obtaining and low reaction activity can mildly and efficiently react with the cyanation reagent with low toxicity to prepare the aromatic nitrile compound or heteroaromatic nitrile compound; and the preparation method has advantages of simple operation, mildness, high efficiency and the like, and further has characteristics of good functional group compatibility, good universality of substrate and the like.
- -
-
Paragraph 0043; 0045; 0198-0200
(2018/11/03)
-
- Organo-Photoredox Catalyzed Oxidative Dehydrogenation of N-Heterocycles
-
We report here for the first time the catalytic oxidative dehydrogenation of N-heterocycles by a visible-light organo-photoredox catalyst with low catalyst loading (0.1–1 mol %). The reaction proceeds efficiently under base- and additive-free conditions with ambient air at room temperature. The utility of this benign approach is demonstrated by the synthesis of various pharmaceutically relevant N-heteroarenes such as quinoline, quinoxaline, quinazoline, acridine, and indole.
- Sahoo, Manoj K.,Jaiswal, Garima,Rana, Jagannath,Balaraman, Ekambaram
-
supporting information
p. 14167 - 14172
(2017/10/16)
-
- General and Mild Nickel-Catalyzed Cyanation of Aryl/Heteroaryl Chlorides with Zn(CN)2: Key Roles of DMAP
-
A new and general nickel-catalyzed cyanation of hetero(aryl) chlorides using less toxic Zn(CN)2 as the cyanide source has been developed. The reaction relies on the use of inexpensive NiCl2·6H2O/dppf/Zn as the catalytic system and DMAP as the additive, allowing the cyanation to occur under mild reaction conditions (50-80 °C) with wide functional group tolerance. DMAP was found to be crucial for successful transformation, and the reaction likely proceeds via a Ni(0)/Ni(II) catalysis based on mechanistic studies. The method was also successfully extended to aryl bromides and aryl iodides.
- Zhang, Xingjie,Xia, Aiyou,Chen, Haoyi,Liu, Yuanhong
-
supporting information
p. 2118 - 2121
(2017/04/27)
-
- C?H Cyanation of 6-Ring N-Containing Heteroaromatics
-
Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.
- Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Johnson, Tarn C.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,MacCoss, Malcolm,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.,Dixon, Darren J.
-
supporting information
p. 14733 - 14737
(2017/10/07)
-
- Synthesis of nitriles from aldehydes with trimethylphenylammonium tribromide and ammonium acetate
-
Various aromatic and heterocyclic aldehydes were easily converted to respective nitriles with the combination of trimethylphenylammonium tribromide and ammonium acetate in good yields at room temperature.
- Sayama, Shinsei
-
p. 1796 - 1802
(2016/11/06)
-
- Luminogenic and fluorogenic compounds and methods to detect molecules or conditions
-
A method to detect the presence or amount of at least one molecule in a sample which employs a derivative of luciferin or a derivative of a fluorophore is provided.
- -
-
Paragraph 0222; 0223
(2016/07/27)
-
- Iodine-catalyzed ammoxidation of methyl arenes
-
The development of organic transformation using cheap and readily available substrates under mild conditions will be pivotal for green and sustainable synthetic organic chemistry. Concerning our continued interest in the cyanation reaction, a metal-free direct ammoxidation of readily available methyl arenes leading to nitriles was established under mild conditions. A series of aryl methanes especially heteroaryl methanes (30 examples) were applicable in moderate to good yields with good functionality tolerance.
- Guo, Songjin,Wan, Gen,Sun, Song,Jiang, Yan,Yu, Jin-Tao,Cheng, Jiang
-
supporting information
p. 5085 - 5088
(2015/03/30)
-
- The synthesis of tetrazoles in nanometer aqueous micelles at room temperature
-
A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature. We have designed a new nonionic amphiphile (GPGS-1500) for the synthesis of tetrazoles in water at room temperature. The reaction conditions were optimized, and the size of the micelles formed by GPGS-1500 in water was measured by dynamic light scattering. Copyright
- Xie, Aming,Cao, Meiping,Liu, Yangyang,Feng, Liandong,Hu, Xinyu,Dong, Wei
-
p. 436 - 441
(2014/01/23)
-
- The Synthesis of Tetrazoles in Nanometer Aqueous Micelles at Room Temperature
-
A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature.
- Xie, Aming,Cao, Meiping,Liu, Yangyang,Feng, Liandong,Hu, Xinyu,Dong, Wei
-
p. 436 - 441
(2015/10/05)
-
- (Benzo[h])quinolinyl-substituted monoazatriphenylenes: Synthesis and photophysical properties
-
We propose a method for the synthesis of quinolinyl- and benzo[h]quinolinylmonoazatriphenylenes through 1,2,4-triazine intermediates with subsequent transformations in aza-Diels-Alder reaction. The photophysical properties of these new compounds were examined, and the effects due to additional fused aromatic rings were explored.
- Kopchuk,Khasanov,Kovalev,Kim,Nikonov,Zyryanov,Rusinov,Chupakhin
-
p. 864 - 870
(2015/09/28)
-
- Rollover cyclometalation with 2-(2′-pyridyl)quinoline
-
Rollover cyclometalation of 2-(2′-pyridyl)quinoline, L, allowed the synthesis of the family of complexes [Pt(L-H)(X)(L′)] and [Pt(L)(X)(L′)][BF4] (X = Me, Cl; L′ = neutral ligand), the former being the first examples of Pt(II) rollover complexes derived from the ligand L. The ligand L* is a C,N cyclometalated, N-protonated isomer of L, and can also be described as an abnormal-remote pyridylene. The corresponding [Pt(L-H)(Me)(L′)]/[Pt(L)(Me)(L′)]+ complexes constitute an uncommon Bronsted-Lowry acid-base conjugated couple. The species obtained were investigated in depth through NMR and UV-vis spectroscopy, cyclic voltammetry, and density functional theory (DFT) methods to correlate different chemico-physical properties with the nature of the cyclometalated ligand (e.g., L vs bipy or L* vs L) and of the neutral ligand (DMSO, CO, PPh3). The crystal structures of [Pt(L-H)(Me)(PPh3)], [Pt(L-H)(Me)(CO)] and [Pt(L)(Me)(CO)][BF 4] were determined by X-ray powder diffraction methods, the latter being the first structure of a Pt(II)-based, protonated, rollover complex to be unraveled. The isomerization of [Pt(L)(Me)(PPh3)]+ in solution proceeds through a retro-rollover process to give the corresponding adduct [Pt(L)(Me)(PPh3)]+, where L acts as a classical N,N chelating ligand. Notably, the retro-rollover reaction is the first process, among the plethora of Pt-C bond protonolysis reactions reported in the literature, where a Pt-C(heteroaryl) bond is cleaved rather than a Pt-C(alkyl) one.
- Zucca, Antonio,Cordeschi, Diletta,Maidich, Luca,Pilo, Maria Itria,Masolo, Elisabetta,Stoccoro, Sergio,Cinellu, Maria Agostina,Galli, Simona
-
p. 7717 - 7731
(2013/07/26)
-
- Manganese oxide promoted liquid-phase aerobic oxidative amidation of methylarenes to monoamides using ammonia surrogates
-
In the presence of amorphous MnO2, various methylarenes (even with two or more methyl groups) could be selectively converted into the corresponding primary monoamides in moderate to high yields. The observed catalysis was truly heterogeneous, and the retrieved amorphous MnO2 catalyst could be reused without an appreciable loss of its catalytic performance. Copyright
- Wang, Ye,Yamaguchi, Kazuya,Mizuno, Noritaka
-
supporting information; experimental part
p. 7250 - 7253
(2012/08/28)
-
- Sulfate additives generate robust and highly active palladium catalysts for the cyanation of aryl chlorides
-
The use of sulfate additives such as H2SO4 greatly increases the reactivity of palladium catalysts for the cyanation of aryl and heteroaryl chlorides and renders them more robust toward adventitious air. Using this method, a wide variety of aromatic and heteroaromatic nitriles were prepared in high yield.
- Shevlin, Michael
-
experimental part
p. 4833 - 4836
(2010/10/02)
-
- Synthesis of quinolinyl and isoquinolinyl phenyl ketones as novel agonists for the cannabinoid CB2 receptor
-
A series of quinolinyl and isoquinolinyl phenyl ketones was synthesized and their CB2 receptor-dependent G-protein activities were determined using the [35S]GTPγS binding assay. Both quinoline and isoquinoline derivatives exhibited similar CB2 receptor agonist activity, the most potent ligands being the 2-(Me2N)-phenyl substituted derivatives, which were also full agonists at the CB2-receptor.
- Reux, Bastien,Nevalainen, Tapio,Raitio, Katri H.,Koskinen, Ari M.P.
-
experimental part
p. 4441 - 4447
(2009/11/30)
-
- 8-substituted-6-trifluoromethyl-9-pyrido[3,2-g]quinoline compounds as androgen receptor modulators
-
Non-steroidal compounds and compositions which are agonists, partial agonists, and antagonists for androgen receptors and methods of preparation for the non-steroidal compounds and compositions.
- -
-
-
- Palladium-catalyzed cyanation of aryl and heteroaryl iodides with copper(i) cyanide
-
The palladium-catalyzed cyanation of aryl and heteroaryl iodides or bromides using copper(i) cyanide as a cyano group source afforded the corresponding aryl and heteroaryl cyanides in good yields.
- Sakamoto, Takao,Ohsawa, Kazutoshi
-
p. 2323 - 2326
(2007/10/03)
-
- PREPARATION OF HETEROARENECARBONITRILES BY REACTION OF HETEROARENE N-OXIDES WITH TRIMETHYLSILYL CYANIDE IN THE PRESENCE OF DBU
-
Several heteroarenecarbonitriles were prepared from the corresponding heteroarene N-oxides by treatment with trimethylsilylcyanide (TMSCN) in the presence of a base in tetrahydrofuran (THF). 1,8-Diazabicyclo-7-undecene (DBU) was found to be an effective base for the cyanation.
- Miyashita, Akira,Kawashima, Touru,Iijima, Chihoko,Higashino, Takeo
-
p. 211 - 218
(2007/10/02)
-
- Sels de N-Alcoxyquinoleinium et de N-Alcoxyisoquinoleinium Porteurs d'une Fonction Ester dans leur Chaine Alcoxyle: Synthese et Reactivite vis-a-vis des Ions Cyanure
-
Reaction of ethyl α-bromoisobutyrate on quinoline 1 oxide and isoquinoline 2-oxide in the presence of silver perchlorate leads to the corresponding N-alkoxyl salts 1 and 2.On treatment with potassium cyanide, these salts are converted into 2-cyanoquinoline and 1-cyanoisoquinoline according to mode B of the Katritzky's classification concerning the reaction of nucleophiles on N-alkoxypyridinium salts.When the reaction of canide ions were performed on salt 1 at 0 deg C in aqueous solution the dihydro aromatic adduct 4 was isolated.This result confirms the addition-elimination mechanism of the reaction studied.
- Sliwa, Henri,Randria-Raharimanana, Clarisse,Ouattara, Lassina
-
p. 627 - 630
(2007/10/02)
-
- Photochemical Reaction of Ethoxycarbonyl-Substituted Quinolines
-
The photochemical reactions of the quinoline derivatives substituted by an ethoxycarbonyl group at the 2-, 3-, and 4-positions of a quinoline nucleus have been investigated in several alcohols and cyclohexane.Irradiation of ethyl 4-quinolinecarboxylate (1) yielded ethyl 2-hydroxyalkyl-4-quinolinecarboxylates (4a-c) in alcohols and ethyl 2-cyclohexyl-4-quinolinecarboxylate (4d) in cyclohexane in a good yield, respectively.The photochemical reactions of ethyl 3-quinolinecarboxylate (2) showed remarkable solvent dependency.Irradiation in methanol and cyclohexane afforded a solvent-additive product, ethyl 4-hydroxymethyl-1,4-dihydro-3-quinolinecarboxylate (5a) and ethyl 4-cyclohexyl-1,4-dihydro-3-quinolinecarboxylate (5b), while such photoaddition of the solvent did not proceed in ethanol and 2-propanol but instead ethyl 1,4-dihydro-3-quinolinecarboxylate (6) and dimeric compounds were formed, both of which were unstable and finally reverted to 2 at room temperature in air.In the case of ethyl 2-quinolinecarboxylate two types of the products, ethyl 4-hydroxyalkyl-1,4-dihydro-2-quinolinecarboxylate (7) and ethyl 1,4-dihydro-2-quinolinecarboxylate (8) were obtained in ethanol and 2-propanol but the yields of those products were poor.On the basis of triplet quenching experiments, the photochemical reactions of those ethyl quinolinecarboxylates are suggested to occur through hydrogen abstraction from the solvents by the ring nitrogen in the S1 state.
- Ono, Isao,Hata, Norisuke
-
p. 2891 - 2898
(2007/10/02)
-
- Angiotensin converting enzyme inhibitors: N-substituted monocyclic and bicyclic amino acid derivatives
-
The synthesis of N-(3-mercaptopropionyl)-N-arylglycines (14a-x), -N-arylalanines (15a,b), -N-cycloalkylglycines (16a-k), and -1,2,3,4-tetrahydroisoquinoline-3-carboxylic acids (17a-d), -1,2,3,4-tetrahydroquinoline-2-carboxylic acids (18a-f), and -indoline-2-carboxylic acids (19a-k) is described. In vitro inhibition of angiotensin converting enzyme (ACE) is reported for each compound, and the structure-activity relationship for each series is discussed. The in vivo inhibition of ACE and antihypertensive effects of representative compounds from each series are discussed. The most potent compound, 19d, had an in vitro ACE IC50 of 2.6 x 10-9 M and lowered blood pressure in spontaneous hypertensive rats 85 mm at a dose of 10 mg/kg po.
- Stanton,Gruenfeld,Babiarz,Ackerman,Friedmann,Yuan,Macchia
-
p. 1267 - 1277
(2007/10/02)
-
- NEW METHODS AND REAGENTS IN ORGANIC SYNTHESIS. 12. REACTION OF DIETHYL PHOSPHOROCYANIDATE (DEPC) WITH AROMATIC AMINE OXIDES. A MODIFIED REISSERT-HENZE REACTION
-
Diethyl phosphorocyanidate (DEPC) reacts with aromatic amine oxides in the presence of triethylamine to give α-cyanated compounds; the reaction may be called a modified Reissert-Henze reaction.
- Harusawa, Shinya,Hamada, Yasumasa,Shioiri, Takayuki
-
p. 981 - 984
(2007/10/02)
-
- Photoinitiated Radical-Forming Reactions of 2-Quinolinecarbonitrile At 77 and 331 K
-
The photoinitiated dimerization of 2-quinolinecarbonitrile (1) in HCl-acidified 2-propanol/water (4:1) has been studied at 77 and 331 K at 250, 300 and 350 nm in unsensitized and benzophenone- and biphenyl-sensitized reactions.One principal product, a dimer lactam (5), is formed at all wavelengths through a triplet state of 1.ESR spectra taken in ethanol at 77 K show a signal for ethyl radical which is formed by a biphotonic process with 1 in acid solution.A mechanism is proposed for the reaction at 331 K which involves an electron transfer from 2-propanol to an upper triplet state of 1.
- Caronna, Tullio,Morrocchi, Sergio,Vittimberga, Bruno M.
-
-
- Trichloromethylquinolines: Synthesis and Reaction with Trimethyl Phosphite
-
Heating of methylquinolines (1, 3, 6, and 12) with phosphorus pentachloride in phosphoryl chloride gave the corresponding trichloromethylquinoline derivatives (2, 4, 9, and 14).Similar treatment of 4-chloro-2-methyl-3-nitroquinoline (16) gave 4-chloro-2-dichloromethyl-3-nitroquinoline (17), 4-chloro-3-nitro-2-trichloromethylquinoline (18), and 3,4-dichloro-2-cyanoquinoline (19).The reaction of 2-trichloromethylquinolines (2, 9, and 18) with trimethyl phosphite gave the corresponding methylated products, 2-(1,1-dichloroethyl)quinolines (21, 24, and 27).However, 4-trichloromethylquinolines (4 and 14) reacted with trimethyl phosphite under similar conditions to give 4-dichloromethylquinolines (23 and 13).Keywords - chlorination; dichloromethylquinolines; trichloromethylquinolines; phosphorus pentachloride, phosphoryl chloride, trimethyl phosphite; methylation; phosphorylation; 2-(1,1-dichloroethyl)quinolines.
- Kato, Tetsuzo,Katagiri, Nobuya,Wagai, Akihiro
-
p. 1069 - 1075
(2007/10/02)
-
- Synthetic Applications of N-N Linked Heterocycles. Part 10. Preparation of Novel N-N Linked Biheteroaryl Monocations, their Reactions with Nucleophiles, and Electrophilic Reactions of some Dihydro-derivatives
-
Novel N-N linked biheteroaryl monocations are prepared from N-aminopyridinium, -quinolinium, or -isoquinolinium salts, with dehydroacetic acid, cyclic anhydrides, hexane-2,4-dione, or the benzoxazinone (15).Reactions of dihydro-derivatives (from reduction of the cations with sodium borohydride or sodium dithionite) with electrophiles are investigated.Reactivity towards nucleophiles was studied to evaluate, (a) the regioselectivity of nucleophilic addition, and (b) the ease of decomposition of the resulting adducts into 4-substituted pyridines.
- Katritzky, Alan R.,Ibrahim, M. Hussain,Valnot, Jean-Yves,Sammes, Michael P.
-
p. 859 - 881
(2007/10/02)
-
- Air oxidation of Reissert compounds
-
Reissert compounds undergo autoxidation in basic solution giving rise to isoquinaldo- or quinaldonitriles.Under the same reaction conditions, dihydroisoquinoline Reissert compounds undergo oxidative decyanation to dihydroisocarbostirils.The intermediacy of α-peroxycyanides is proposed in this transformation.
- Rozwadowska, Maria,Brozda, Danuta
-
p. 1239 - 1242
(2007/10/02)
-