- Palladium-Catalyzed Reductive Aminocarbonylation of Benzylammonium Triflates with o-Nitrobenzaldehydes for the Synthesis of 3-Arylquinolin-2(1 H)-ones
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A palladium-catalyzed straightforward procedure for the synthesis of 3-arylquinolin-2(1H)-ones has been developed. The synthesis proceeds through a palladium-catalyzed reductive aminocarbonylation reaction of benzylic ammonium triflates with o-nitrobenzaldehydes, and a wide range of 3-arylquinolin-2(1H)-ones was obtained in moderate to good yields with very good functional group compatibility.
- Liu, Yongzhu,Qi, Xinxin,Wu, Xiao-Feng
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p. 13824 - 13832
(2021/10/12)
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- Palladium-catalyzed carbonylative synthesis of 3-arylquinolin-2(1H)-ones from benzyl chlorides and o-nitrobenzaldehydes
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A palladium-catalyzed carbonylative cyclization of benzyl chlorides with o-nitrobenzaldehydes has been developed for the synthesis of 3-arylquinolin-2(1H)-ones. Mo(CO)6 played a dual role as both a CO surrogate and a reductant in this carbonylative transformation.
- Hou, Chen-Yang,Liu, Jian-Li,Qi, Xinxin,Wu, Xiao-Feng
-
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- Solvent-Dependent Cyclization of 2-Alkynylanilines and ClCF2COONa for the Divergent Assembly of N-(Quinolin-2-yl)amides and Quinolin-2(1 H)-ones
-
Herein, we present an expedient Cu-catalyzed [5 + 1] cyclization of 2-alkynylanilines and ClCF2COONa to divergent construction of N-(quinolin-2-yl)amides and quinolin-2(1H)-ones by regulating the reaction solvents. Notably, nitrile acts as a solvent and performs the Ritter reactions. ClCF2COONa is used as a C1 synthon in this transformation, which also represents the first example for utilization of ClCF2COONa as an efficient desiliconization reagent. The current protocol involves in situ generation of isocyanide, copper-activated alkyne, Ritter reaction and protonation.
- Wang, Ya,Zhou, Yao,Ma, Xingxing,Song, Qiuling
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p. 5599 - 5604
(2021/08/01)
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- Preparation method of 3-aryl quinoline-2 (1H) ketone derivative
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The invention discloses a preparation method of a 3-aryl quinoline-2 (1H) ketone derivative. The method comprises the following steps: carrying out a reaction on palladium acetate, S)-1, 1'-binaphthyl-2, 2'-diphenylphosphine, carbonyl molybdenum, triethylamine, water, benzisoxazole and a benzyl chloride compound at 100 DEG C for 26 hours, and after the reaction is completed, carrying out post-treatment to obtain the 3-aryl quinoline-2 (1H) ketone derivative. According to the preparation method, benzisoxazole is used as a nitrogen source and a formyl source, the operation is simple, the reaction initial raw materials are cheap and easy to obtain, the tolerance range of substrate functional groups is wide, and the reaction efficiency is high; and various 3-aryl quinoline-2 (1H) ketone derivatives can be synthesized according to actual needs, and the practicability of the method is widened while the operation is convenient.
- -
-
Paragraph 0032-0040
(2021/07/01)
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- Palladium-catalyzed carbonylative cyclization of benzyl chlorides with anthranils for the synthesis of 3-arylquinolin-2(1: H)-ones
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An efficient carbonylative procedure for the synthesis of 3-arylquinoin-2(1H)-ones has been established. Through a palladium-catalyzed aminocarbonylation of benzyl chlorides with anthranils, a variety of 3-arylquinoin-2(1H)-one products were obtained in moderate to excellent yields with good functional group tolerance. This journal is
- Liu, Jian-Li,Xu, Ren-Rui,Wang, Wei,Qi, Xinxin,Wu, Xiao-Feng
-
supporting information
p. 3584 - 3588
(2021/05/04)
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- Regio- And Stereoselective Synthesis of Diverse 3,4-Dihydro-2-quinolones through Catalytic Hydrative Cyclization of Imine- And Carbonyl-Ynamides with Water
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Transition-metal-catalyzed alkyne hydration reaction has attracted considerable interest in the past decades because this approach would lead to the facile and efficient formation of synthetically useful carbonyls. However, transition-metal-catalyzed alky
- Zhu, Bo-Han,Zhang, Ying-Qi,Xu, Hao-Jin,Li, Long,Deng, Guo-Cheng,Qian, Peng-Cheng,Deng, Chao,Ye, Long-Wu
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p. 1706 - 1713
(2021/02/09)
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- Palladium-Catalyzed C-C Bond Activation of Cyclopropenone: Modular Access to Trisubstituted α,β-Unsaturated Esters and Amides
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Strain-driven palladium/N-heterocyclic carbene-catalyzed C-C bond activation of diphenylcyclopropenone (DPC) has been explored for one-step access to trisubstituted α,β-unsaturated esters and amides. The designed transformation works under mild conditions providing exclusively a single stereoisomer. Mechanistic studies support the oxidative addition of the C-C bond of cyclopropenone to in-situ-generated Pd(0) intermediate. We have proved that vinylic hydrogen in the product is coming from phenol/aniline through deuterium-labeling studies. Late-stage functionalization of bioactive molecules such as procaine, estrone, and hymecromone demonstrates the robustness of this protocol.
- Nanda, Tanmayee,Biswal, Pragati,Pati, Bedadyuti Vedvyas,Banjare, Shyam Kumar,Ravikumar, Ponneri Chandrababu
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p. 2682 - 2695
(2021/02/01)
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- Supported Palladium Nanoparticles-Catalyzed Synthesis of 3-Substituted 2-Quinolones from 2-Iodoanilines and Alkynes Using Oxalic Acid as C1 Source
-
3-Aryl/alkyl-2-quinolones were synthesized employing microwave assisted multicomponent reaction of 2-iodoanilines, terminal alkynes and oxalic acid dihydrate ((CO2H)2 ? 2H2O) under polystyrene supported palladium (Pd@PS) nanoparticles-catalyzed conditions. The use of a heterogeneous palladium catalyst was explored first time for 2-quinolone synthesis involving carbonylation reaction employing (CO2H)2 ? 2H2O as a solid and bench stable carbon monoxide (CO) source. The reaction exhibited good substrate generality for 2-iodoanilines and alkynes with wide functional group tolerance and good regio-selectivity. The ligand free operation, recyclability of heterogeneous Pd@PS catalyst and use of bench stable C1 source are the invaluable merits of the protocol. (Figure presented.).
- Thakur, Vandna,Sharma, Ajay,Yamini,Sharma, Nishtha,Das, Pralay
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p. 426 - 431
(2018/12/13)
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- Sulfinates and thiocyanates triggered 6-endo cyclization of o-alkynylisocyanobenzenes
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Diverse 2-sulfonyl- and 2-thiocyanato-3-substituted quinolines were synthesized from o-alkynylisocyanobenzenes by nucleophilic addition of the respective sulfinate sodium salts and ammonium thiocyanate to the isocyanide moiety followed by cyclization. The salient features of the methodology include metal-free, ambient temperature and mild reaction conditions, ease of reagent handling, and broad functional group tolerance.
- Khaikate, Onnicha,Meesin, Jatuporn,Pohmakotr, Manat,Reutrakul, Vichai,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
-
supporting information
p. 8553 - 8558
(2018/12/01)
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- Synthesis of 3-substituted quinolin-2(1H)-ones via the cyclization of o-alkynylisocyanobenzenes
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A facile synthesis of various functionalized 3-substituted quinolin-2(1H)-ones through Ag(i) nitrate-catalyzed cyclization of o-alkynylisocyanobenzenes is described. The reaction allows rapid and convenient access to 3-substituted quinolin-2(1H)-one scaffolds in moderate to good yields.
- Charoenpol, Ailada,Meesin, Jatuporn,Khaikate, Onnicha,Reutrakul, Vichai,Pohmakotr, Manat,Leowanawat, Pawaret,Soorukram, Darunee,Kuhakarn, Chutima
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p. 7050 - 7054
(2018/10/17)
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- Regioselective C-3 arylation of coumarins with arylhydrazines via radical oxidation by potassium permanganate
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An efficient protocol for oxidative C-3 arylation of coumarins with arylhydrazine has been developed using potassium permanganate as an oxidant. The arylated coumarins with different electronic properties were obtained in moderate to good yields. The deve
- Yuan, Jin-Wei,Li, Wei-Jie,Yang, Liang-Ru,Mao, Pu,Xiao, Yong-Mei
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p. 1115 - 1123
(2016/11/16)
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- Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study
-
Combined experimental and theoretical investigations into the phenyliodine bis(trifluoroacetate) (PIFA)-mediated reaction of N-arylcinnamamide to produce 3-arylquinolin-2-one derivatives have been conducted. High regioselectivity during the aryl migration process was observed in 3,3-disubstituted acrylamides. Density functional theory calculation was conducted in an attempt to understand the mechanism and the origin of the regioselectivity. On the basis of both the experimental and the theoretical results, a mechanism involving an oxidative annulation, followed by an aryl migration, has been proposed. The annulation is the regioselectivity determining step.
- Liu, Le,Zhang, Tonghuan,Yang, Yun-Fang,Zhang-Negrerie, Daisy,Zhang, Xinhao,Du, Yunfei,Wu, Yun-Dong,Zhao, Kang
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p. 4058 - 4065
(2016/06/08)
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- KMnO4/AcOH-mediated C3-selective direct arylation of coumarins with arylboronic acids
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An efficient protocol for KMnO4/AcOH-mediated dehydrogenative direct radical arylation of coumarins with arylboronic acids to afford 3-arylcoumarin derivatives is described. A similar reaction system is also applicable to the 3-arylation of quinolinone derivatives. These KMnO4/AcOH-mediated coupling reactions occur regioselectively at the C3 position of coumarins and quinolinones. Some notable features of this method are high efficiency, moderate to good yield, and a broad group tolerance.
- Yuan, Jin-Wei,Yang, Liang-Ru,Yin, Qiu-Yue,Mao, Pu,Qu, Ling-Bo
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p. 35936 - 35944
(2016/05/19)
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- Base catalysed intermolecular cyclisation of N-protected o-amino benzaldehyde/acetophenone with phosphorus/sulphur based allenes: facile synthesis of substituted quinolines
-
Reaction of N-Bz protected o-aminobenzaldehyde or acetophenone with allenylphosphonates in the presence of a simple base leads to quaternary carbon substituted phosphono-quinolines which undergo thermal rearrangement to O-phosphorylated quinolines. The pr
- Anitha, Mandala,Gangadhararao,Kumara Swamy
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p. 3591 - 3602
(2016/04/19)
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- Transformations of anilides of 3-aryl-2,3-epoxypropionic acids when exposed to acidic agents
-
Anilides of 3-aryl-2,3-epoxypropionic acids on treatment with aqueous HBr gave 3-aryl-3-bromo-2-hydroxypropionic acid anilides and (in some cases) 2-bromo-3-hydroxy regioisomers. Cyclization of these products into 3-arylquinolin-2(1H)-ones was studied.
- Mamedov,Mamedova,Khikmatova,Samigullina,Gubaidullin,Bazanova,Rizvanov, I. Kh.,Sinyashin
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p. 2857 - 2864
(2016/09/28)
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- Synthesis of quinolinones with palladium-catalyzed oxidative annulation between acrylamides and arynes
-
An unprecedented palladium-catalyzed oxidative annulation of acrylamides with benzyne precursors has been successfully developed. By using this mild "N-H activation/Heck reaction" method, a wide variety of quinolinones were conveniently prepared in one st
- Wang, Weiguo,Peng, Xianglong,Qin, Xiaoyu,Zhao, Xiangyun,Ma, Chen,Tung, Chen-Ho,Xu, Zhenghu
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p. 2835 - 2841
(2015/03/18)
-
- Metal-free ring expansion of indoles with nitroalkenes: A simple, modular approach to 3-substituted 2-quinolones
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3-Substituted 2-quinolones are obtained via a novel metal-free transannulation reaction of 2-nitroolefins with 2-substituted indoles in polyphosphoric acid. This acid-mediated cascade transformation operates via the ANRORC (Addition of Nucleophile, Ring Opening, and Ring Closure) mechanism and can be used in combination with the Fisher indole synthesis to offer a practical three-component hetero-annulation approach to 2-quinolones from arylhydrazines, 2-nitroalkenes, and acetophenone. An alternative entry to this chemistry employing the alkylation of electron-rich arenes and hetarenes with 1-(2-indolyl)-2-nitroalkene has also been demonstrated.
- Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Matheny, Jonathon P.,Rubin, Michael
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p. 8647 - 8656
(2015/03/03)
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- Highly efficient modular metal-free synthesis of 3-substituted 2-quinolones
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A modular approach to 3-substituted 2-quinolones via a cascade annulation reaction between 4-nitroketones and hydrazines has been developed.
- Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Bijieva, Asiyat S.,Rubin, Michael
-
supporting information
p. 9786 - 9788
(2014/12/12)
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- Metal-free transannulation reaction of indoles with nitrostyrenes: A simple practical synthesis of 3-substituted 2-quinolones
-
3-Substituted 2-quinolones are obtained via a novel, metal-free transannulation reaction of 2-substituted indoles with 2-nitroalkenes in polyphosphoric acid. The reaction can be used in conjunction with the Fisher indole synthesis offering a practical three-component heteroannulation methodology to produce 2-quinolones from arylhydrazines, 2-nitroalkenes and acetophenone.
- Aksenov, Alexander V.,Smirnov, Alexander N.,Aksenov, Nicolai A.,Aksenova, Inna V.,Frolova, Liliya V.,Kornienko, Alexander,Magedov, Igor V.,Rubin, Michael
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supporting information
p. 9305 - 9307
(2013/10/01)
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- PhI(OCOCF3)2-mediated C-C bond formation concomitant with a 1,2-Aryl shift in a metal-free synthesis of 3-arylquinolin-2-ones
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The reaction of the readily available N-methyl-N-phenylcinnamamides with phenyliodine bis(trifluoroacetate) (PIFA) in the presence of Lewis acids provides a general and efficient assembly of a variety of 3-arylquinolin-2-one compounds. This novel approach features not only metal-free oxidative C(sp 2)-C(sp2) bond formation but also an exclusive 1,2-aryl migration.
- Liu, Le,Lu, Hang,Wang, Hong,Yang, Chao,Zhang, Xiang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
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p. 2906 - 2909
(2013/07/26)
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- Copper(I) iodide catalyzed synthesis of quinolinones via cascade reactions of 2-halobenzocarbonyls with 2-arylacetamides
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An efficient copper-catalyzed method for the synthesis of quinolinones, pyridinones, and heteroannulated pyridinones via cascade reactions of substituted 2-iodo-, 2-bromo-, and 2-chlorobenzocarbonyls with 2-arylacetamides is reported. The protocol works well for the reaction of most of the 2-iodo-, 2-bromo- and 2-chlorobenzocarbonyls with 2-arylacetamides. Georg Thieme Verlag Stuttgart · New York.
- Fu, Liangbing,Huang, Xiaoli,Wang, Deping,Zhao, Pinghua,Ding, Ke
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experimental part
p. 1547 - 1554
(2011/06/25)
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- Microwave-assisted, palladium-catalyzed carbonylative cyclization - Rapid synthesis of 2-quinolones from unprotected 2-iodoanilines and terminal alkynes
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Palladium-catalyzed cyclocarbonylations of 2-iodoanilines with various terminal alkynes have been carried out by the use of commercially available molybdenum hexacarbonyl as a convenient and solid carbon monoxide source. The reactions were conducted at 160 °C for 30 min under microwave irradiation and in the presence of Et3N in THF, affording the corresponding 2-quinolone derivatives in good regioselectivities and yields.
- Chen, Jia-Rong,Liao, Jie,Xiao, Wen-Jing
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experimental part
p. 331 - 337
(2010/07/08)
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- Preparation of 2-Quinolones by sequential heck reduction-cyclization (HRC) reactions by using a multitask palladium catalyst
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One-pot sequential Heck reduction-cyclization (HRC) reactions leading to the synthesis of substituted 2-quinolones have been developed by using a heterogeneous or mixed homogeneous/heterogeneous multitask palladium catalyst with charcoal as a support. The whole sequence occurs under very mild conditions without the need for additives (ligand or base) by taking advantage of the high reactivity of aryldiazonium salts as "super electrophiles". Recycling experiments showed that the reused heterogeneous Pd°/C catalyst was not able to promote another HRC sequence but was, however, still highly active for hydrogenation, hydrodehalogenation, as well as hydrogenolysis reactions.
- Felpin, Francois-Xavier,Coste, Jerome,Zakri, Cecile,Fouquet, Eric
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experimental part
p. 7238 - 7245
(2010/03/25)
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- A general synthesis of quinolinones and benzothiazine 1,1-dioxides via ring closing metathesis
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A general synthesis of quinolinones and benzothiazine 1,1-dioxides is presented. A series of N-phenylacrylamides and N-phenylethylenesulfonamides were studied for their ability to undergo ring closing methathesis to yield the corresponding quinolinones and benzothiazine 1,1-dioxides, respectively. The reactions are general in scope and represents a mild method for the preparation of these heterocycles.
- Minville, Joannie,Poulin, Jason,Dufresne, Claude,Sturino, Claudio F.
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p. 3677 - 3681
(2008/09/20)
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- Intramolecular amidation - An efficient synthesis of 3-aryl-2-quinolinones
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To reveal the scope of the syntheses of 3-aryl-2-quinolinones from 2-nitro-α-phenylcinnamic acids, the isomerization of (E)-2-amino-α- phenylcinnamic acids was studied. The results showed that (E)-2-amino-α- phenylcinnamic acids were isomerized to its (Z)
- Luo, Yinggang,Tao, Feiyan,Liu, Yan,Li, Bogang,Zhang, Guolin
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p. 1620 - 1625
(2007/10/03)
-
- Discovery of 2,3,5-trisubstituted pyridine derivatives as potent Akt1 and Akt2 dual inhibitors
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This letter describes the discovery of a novel series of dual Akt1/Akt2 kinase inhibitors, based on a 2,3,5-trisubstituted pyridine scaffold. Compounds from this series, which contain a 5-tetrazolyl moiety, exhibit more potent inhibition of Akt2 than Akt1.
- Zhao, Zhijian,Leister, William H.,Robinson, Ronald G.,Barnett, Stanley F.,Defeo-Jones, Deborah,Jones, Raymond E.,Hartman, George D.,Huff, Joel R.,Huber, Hans E.,Duggan, Mark E.,Lindsley, Craig W.
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p. 905 - 909
(2007/10/03)
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- Facile synthesis of 3-substituted and 1,3-disubstituted quinolin-2(1H)-ones from 2-nitrobenzaldehydes
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2-Nitrobenzaldehydes were reduced with iron powder to 2-aminobenzaldehydes, which were reacted immediately with acyl chlorides to provide 2-carboxamidobenzaldehydes (1) with overall yields of 71-90 %. Reaction of 1 with base provided 3-substituted quinolin-2(1H)-ones with 63-97 % yields. Treatment of 1 with methyl iodide and base gave 1-methyl-3-substituted quinolin-2(1H)-ones with 82-95 % yields, whereas the treatment with isopropyl iodide gave 1-isopropyl-3-substituted quinolin-2(1H)-ones with 7-42 % yields.
- Park, Kwanghee Koh,Jung, Jin Young
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p. 2095 - 2105
(2007/10/03)
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- Biradicals/zwitterions from thermolysis of enyne-isocyanates. Application to the synthesis of 2(1H)-pyridones, benzofuro[3,2-c]pyridin-1(2H)-ones, 2,5-dihydro-1H-pyrido[4,3,-b]indol-1-ones, and related compounds
-
Thermolysis of benzannulated enyne-isocyanates 13 and enyne-isocyanates 36 and 37 promoted the cycloaromatization reactions to generate in situ O,4-didehydro-2-hydroxyquinolines and O,4-didehydro-2-hydroxypyridines, respectively, as reactive intermediates. These cycloaromatized intermediates could be captured either as biradicals and/or as zwitterions depending on the nature of the substituent at the alkynyl terminus. The intermediate derived from cycloaromatization of 13a bearing a phenyl substituent could be regarded as biradical 14, which then abstracts hydrogen atoms from γ-terpinene leading to 2(1H)-quinolinone 15. Alternatively, the same intermediate could also be regarded as zwitterion 14′, which then undergoes an initial hydride abstraction from γ-terpinene followed by protonation to produce 15. The presence of a 2-phenylethyl substituent in 13b and 37a or a 2-methylphenyl substituent in 37b also allowed the resulting intermediates to be captured intramolecularly either as biradicals or as zwitterions, producing 2(1H)-quinolinone 19, 2(1H)-pyridone 39, and benzopyranopyridine 43, respectively. On the other hand, with a 2-methoxyphenyl, a 2-(dimethylamino) phenyl, or a 3-methoxypropyl substituent, the chemical behavior of the cycloaromatized adduct could be best accounted for in terms of a zwitterionic intermediate leading to benzofuro [3,2-c]quinolin-6(5H)-one (20), 5,11-dihydro-11-methyl-6H-indolo-[3,2-c]quinolin-6-one (25), benzofuro[3,2-c]pyridin-1(2H)-one 44, 2,5-dihydro-2,5-dimethyl-1H-pyrido-[4,3-b] indol-1-one 46, and related compounds. Interestingly, thermolysis of 37f bearing a 2-(methoxymethyl)phenyl substituent at the alkynyl terminus produced the unexpected benzopyranopyridine 56 as the major product in a process involving the cleavage of the bond between the methoxyl oxygen and the adjacent methylene carbon. The efficiency and selectivity of the cycloaromatization reaction could also be enhanced by the introduction of 1.1 to 10 equiv of dimethylphenylsilyl chloride to the reaction mixture to capture the resulting zwitterion.
- Li, Hongbin,Yang, Hua,Petersen, Jeffrey L.,Wang, Kung K.
-
p. 4500 - 4508
(2007/10/03)
-
- A new synthesis of naphthyridinones and quinolinones: Palladium-catalyzed amidation of o-carbonyl-substituted aryl halides
-
(Equation Presented) An alternative to the Friedlander condensation for the synthesis of naphthyridinones and quinolinones has been discovered. Palladium-catalyzed amidation of halo aromatics substituted in the ortho position by a carbonyl functional group or its equivalent with primary or secondary amides leads to the formation of substituted naphthyridinones and quinolinones.
- Manley, Peter J.,Bilodeau, Mark T.
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p. 2433 - 2435
(2007/10/03)
-
- Palladium-catalyzed carbonylative annulation of terminal alkynes: Synthesis of coumarins and 2-quinolones
-
o-Iodophenols and o-iodoaniline derivatives react with terminal alkynes under 1 atm of CO in the presence of pyridine and catalytic amounts of Pd(OAc)2 to generate coumarins and 2-quinolones, respectively, as the only products. Terminal alkynes bearing alkyl, aryl, silyl, hydroxyl, ester and cyano substituents are effective in these processes affording the desired products in moderate yields. The formation of coumarins and 2-quinolones in this process is in stark contrast with all previously described palladium-catalyzed reactions of o-iodophenols or o-iodoanilines with terminal alkynes and CO, which have afforded chromones and 4-quinolones. Moreover, under our reaction conditions terminal alkynes insert into the carbon-palladium bond instead of undergoing a Sonogashira-type coupling as confirmed by an isotope labeling experiment.
- Kadnikov, Dmitry V.,Larock, Richard C.
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p. 425 - 435
(2007/10/03)
-
- Substituent effects on absorption and fluorescence spectra of carbostyrils
-
Absorption and fluorescence spectra as well as quantum yields of a series of differently substituted carbostyrils (quinolin-2(1H)-ones) are reported. Especially for compounds containing donor substituents in position 6, substantial bathochromic shifts (comparable to analogous coumarins) of both absorption as well as fluorescence transitions are obtained. High absorption intensities and quantum yields are found for 7-donor substituted isomers. Semiempirical molecular orbital calculations (AMI for structures, ZINDO for electronic transition energies) prove to be a suitable tool for the prediction of absorption and fluorescence properties of these compounds. Ab initio and density functional calculations establish the lactam form as the dominant tautomer of the parent quinolin-2(1H)-one.
- Fabian, Walter M.F.,Niederreiter, Karlheinz S.,Uray, Georg,Stadlbauer, Wolfgang
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p. 209 - 220
(2007/10/03)
-
- Synthesis and antiplatelet activity of phenyl quinolones
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In our search for novel antiplatelet agents, seven positional phenyl quinolone isomers were synthesized. Preliminary screening confirmed their inhibitory effects against arachidonic acid (AA)-induced platelet aggregation. Varying the substitutional position of the phenyl group had a profound effect on the antiplatelet activity of these isomers. 3-Phenyl-4-quinolone showed the greatest potency and was superior to indomethacin, although the two structures are quite different. The mechanism and pharmacological action of 3-phenyl-4-quinolone are currently under investigation. Copyright (C) 1998 Elsevier Science Ltd.
- Huang, Li-Jiau,Hsieh, Ming-Chieh,Teng, Che-Ming,Lee, Kuo-Hsiung,Kuo, Sheng-Chu
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p. 1657 - 1662
(2007/10/03)
-
- Metallation of 2(1H)-quinolinone: Synthesis of 3-substituted compounds
-
The ortho-directing effect of the amide function in the regioselective lithiation of 2(1H)-quinolinone has been confirmed. Direct or indirect electrophilic substitution may compete with previous multistep procedures to obtain 3-substituted compounds.
- Fernandez,De La Cuesta,Avendano
-
p. 1362 - 1364
(2007/10/02)
-
- Rhodium-catalyzed carbonylation of 2-alkynylaniline: Syntheses of 1,3-dihydroindol-2-ones
-
Rhodium-catalyzed carbonylation of 2-alkynylanilines under water-gas shift reaction conditions gives 3-alkyl-1,3-dihydroindol-2-ones 2 in good yields along with a small amount of 2-quinolone derivatives 4. The reaction under carbonylation conditions witho
- Hirao, Kojiro,Morii, Noritsugu,Joh, Takashi,Takahashi, Shigetoshi
-
p. 6243 - 6246
(2007/10/02)
-
- Synthesis of Coumarins and Quinolones by Intramolecular Aldol Condensation Reactions of Titanium Enediolates
-
Low-valent titanium prepared by the reduction of TiCl3 with zinc dust oxidatively adds to α-ketoamides or α-ketoesters with the formation of the corresponding titanium enediolates.These 1,2-difunctional nucleophiles, which have hardly been used in organic
- Fuerstner, Alois,Jumbam, Denis N.,Shi, Nongyuan
-
p. 326 - 332
(2007/10/02)
-
- On the Mechanism of Thermal Ring Expansion of 3,3-Dialkyloxindoles
-
13C Labelling experiments show that the title reaction takes place by a free radical mechanism which involves (i) homolysis of the C(3)-alkyl bond, (ii) rearrangement of the resulting 3-indolyl radical to a 3-indolylmethyl radical , (iii) ring expansion by competitive neophyl rearrangement or attack at the carbonyl position, and (iv) aromatisation by loss of a hydrogen atom.
- McNab, Hamish
-
p. 543 - 545
(2007/10/02)
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- New Syntheses of 2-Acylbenzofurans, 2-Acylindoles, 2-Indolylcarboxylates, and 2-Quinolones by Intramolecular Wittig Reaction
-
The title compounds are obtained by intramolecular Wittiig reaction of 2-(α-ketoacyloxy)-, 2-(α-ketoacylamino)-, or 2-benzyltriphenylphosphonium salts, respectively.
- Capuano, Lilly,Ahlhelm, Alfred,Hartmann, Herbert
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p. 2069 - 2074
(2007/10/02)
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- Synthesis of 3-Arylcoumarins, Thiacoumarins and Carbostyrils
-
3-Arylcarbostyrils (2a-f), coumarins (2g-j) and thiacoumarin (2k) have been prepared by a generalised method from α,β-dibromohydrocinnamoyl derivatives (1a-k).The intermediate dihydrocoumarins and dihydrocarbostyrils (3, Y = O, NH) have been prepared which on acid treatment furnish 2.However, treatment of 3 with a base affords the 4-arylcoumarins and carbostyrils (4).
- Natarajan, M.,Manimaran, T.,Ramakrishnan, V. T.
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p. 529 - 534
(2007/10/02)
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- A New Route for the Synthesis of Coumarins, Thiacoumarins and Carbostyrils
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3-Arylcarbostyrils, coumarins and thiacoumarins (3) have been prepared from the respective β-aryl-α-bromodihydrocinnamoyl derivatives (2) by treatment with AlCl3.The β,β-diarylacrylic acid derivatives (4) and (9), obtained from 2, on reaction with AlCl3 afford 4-arylcarbostyrils (5) 6-methyl-4-phenylthiacoumarin (10) respectively.However the oxygen analogs (11) give 3,3-diphenyl-1-indanone (12)
- Natarajan, M.,Ramakrishnan, V. T.
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p. 720 - 727
(2007/10/02)
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- Reactions of Halogenated α-Phenylcinnamic Acids with Potassium Amide in Liquid Ammonia : Part I - Reactions of cis- and trans-2-Chloro-α-phenylcinnamic Acids
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Reaction of trans- and cis-2-chloro-α-phenylcinnamic acids (1) with KNH2 in liquid ammonia gives phenanthrene-9-carboxylic acids (2) and 3-phenylcarbostyrils (8).Under similar conditions 3-chloro-α-phenylcinnamic acids (5) furnish 3-phenylcoumarins (6).
- Kessar, S. V.,Nadir, U. K.,Gupta, Y. P.,Pahwa, P. S.,Singh, Paramjit
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- Carbostyril derivatives used as coccidiostats
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Carbostyril derivatives useful as coccidiostats are prepared by reacting an ortho-halo benzaldehyde with a 2-alkyl-2-oxazoline, then heating at above about 200° C thereby forming the carbostyril.
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- Insecticide evaporator comprising a stabilizer
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Insecticide evaporator comprising at least one volatile phosphoric ester insecticide, an agent for stabilizing the said ester against decomposition by protonization and used in an amount of 0.2 to 20% based on the weight of phosphoric ester, characterized in that the stabilizing agent contains at least one compound selected from the compounds of the chemical class of 1,3-benzodioxoles and at least one diazene.
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- Evaporator system comprising a stabilized pesticidal phosphoric acid ester and method for stabilizing such ester enclosed in an evaporator
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An evaporator system adapted for emitting insect killing vapors of an insecticide therefrom and comprising a liquid or solid composition enclosed therein, said insecticide consisting in at least one volatile phosphoric acid ester which is stabilized by at least one diazene compound.
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