- A Facile Synthesis of 4-Aryl-2H-1-benzopyran-2-ones
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Reaction of 2-hydroxybenzophenones (1, 3, 7, 8) with ethoxycarbonylmethylenetriphenylphosphorane affords 4-aryl-2H-1-benzopyran-2-ones (2, 4-6) in excellent yields. - Keywords: 4-Aryl-2H-1-benzopyran-2-ones; Ethoxycarbonylmethylenetriphenylphosphorane; Friedel-Crafts reaction; 2-Hydroxybenzophenones; Wittig reaction
- Ahluwalia, Vinod K.,Singh, Daljeet,Singh, Rishi P.
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- Cyclization of aryl 3-aryl propynoates into 4-arylcoumarins catalyzed by cyclometalated Platinum(II) complexes
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Cyclometalated (ppy)PtII complexes (ppy = 2-phenylpyridinato-C2,N) catalyze the intramolecular cyclization of aryl propynoates to form coumarins and benzocoumarins. The complex [(ppy)PtCl(MeCN)] (5 mol %) was the most active and effi
- Zaitceva, Olesia,Bénéteau, Valérie,Ryabukhin, Dmitry S.,Eliseev, Ivan I.,Kinzhalov, Mikhal A.,Louis, Benoit,Vasilyev, Aleksander V.,Pale, Patrick
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supporting information
(2020/03/05)
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- Photoinduced cyclization of alkynoates to coumarins with N-Iodosuccinimide as a free-radical initiator under ambient and metal-free conditions
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An efficient photoinduced strategy for the preparation of coumarins was developed. In the presence of N-iodosuccinimide (NIS) as a free-radical initiator and under LED (380–385 nm) irradiation and metal-free conditions, the reaction of alkynoates underwen
- Wang, Zhihui,Li, Xuezhi,Wang, Lei,Li, Pinhua
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p. 1044 - 1051
(2019/01/25)
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- Selectivity Controlled Palladium-Catalyzed Carbonylative Synthesis of Propiolates and Chromenones from Phenols and Alkynes
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An interesting selectivity-controlled palladium-catalyzed oxidative carbonylation procedure for the synthesis of propiolates and chromenones has been developed. Starting from phenols and alkynes, under slightly different conditions, various propiolates an
- Zhu, Fengxiang,Wu, Xiao-Feng
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supporting information
p. 3422 - 3425
(2018/06/11)
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- Rhodium(I)-Catalyzed Decarbonylative Aerobic Oxidation of Cyclic α-Diketones: A Regioselective Single Carbon Extrusion Strategy
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A rhodium-catalyzed decarbonylative aerobic oxidation of cyclic α-diketones has been developed for the first time, where the regioselective formations of α-pyrones and isocoumarins have been achieved. The current decarbonylative aerobic oxidation pathway proceeds via the C-C bond cleavage followed by a C-O bond formation, representing a biomimetic oxidation approach to unsaturated six-membered cyclic lactones. The unique ability of rhodium catalysts to induce the decarbonylative aerobic oxidation opens up a new synthetic toolbox that utilizes the "regioselective single carbon" extrusion strategy.
- Golime, Gangadhararao,Kim, Hun Young,Oh, Kyungsoo
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supporting information
p. 942 - 945
(2018/02/22)
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- Synthesis and in vitro evaluation of leishmanicidal activity of 7-hydroxy-4-phenylcoumarin derivatives
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Eight coumarin derivatives (2–8) were synthesized from 7-hydroxy-4-phenylcoumarin 1 and were evaluated for their in vitro leishmanicidal activity against promastigote and amastigote forms of Leishmania amazonensis, as well their toxicity in murine macroph
- Rosa, Isael A.,de Almeida, Letícia,Alves, Karina F.,Marques, Marcos J.,Fregnan, Ant?nio M.,Silva, Claudinei A.,Giacoppo, Juliana O. S.,Ramalho, Teodorico C.,Carvalho, Diogo T.,dos Santos, Marcelo H.
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p. 131 - 139
(2017/01/12)
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- Cp?Co(III)-Catalyzed Annulations of 2-Alkenylphenols with CO: Mild Access to Coumarin Derivatives
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Cp?Co(III)-catalyzed annulations of 2-alkenylphenols with CO for the synthesis of coumarin derivatives have been developed. The reaction features mild reaction conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies were conducted, suggesting that C-H activation is the turnover limiting step. Furthermore, the efficiency of this reaction was demonstrated by the rapid total synthesis of three natural products herniarin, xanthyletin, and seselin.
- Liu, Xu-Ge,Zhang, Shang-Shi,Jiang, Chun-Yong,Wu, Jia-Qiang,Li, Qingjiang,Wang, Honggen
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supporting information
p. 5404 - 5407
(2015/11/18)
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- Synthesis of 4-arylcoumarins via palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamates with diaryliodonium salts
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The palladium-catalyzed arylation/cyclization of ortho-hydroxylcinnamate ester derivatives by using diaryliodonium(III) salts has been developed. With this method, 4-arylcoumarins were easily prepared in good to excellent yields under base-free conditions
- Yang, Yang,Han, Jianwei,Wu, Xunshen,Xu, Shujia,Wang, Limin
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supporting information
p. 3809 - 3812
(2015/06/08)
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- Single-step synthesis of 4-phenyl and 3,4-dihydro-4-phenyl coumarins using a recyclable Preyssler heteropolyacid catalyst under solvent-free reaction conditions
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4-Phenyl and 3,4-dihydro-4-phenylcoumarins were prepared by direct esterification of phenols with phenylpropiolic and cinnamic acids, respectively, using a compound with Preyssler structure (H14P5NaW30O110) (PA)
- Escobar, Anglica M.,Ruiz, Diego M.,Autino, Juan C.,Romanelli, Gustavo P.
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p. 10109 - 10123
(2016/01/12)
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- Palladium-catalyzed domino protodecarboxylation/oxidative Heck reaction: Regioselective arylation of coumarin-3-carboxylic acids
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A protocol for straightforward and step-economical synthesis of neoflavones from coumarin-3-carboxylic acids is developed. This approach enables controlled protodecarboxylation/regioselective C-H arylation of coumain-3-carboxylic acids in one-pot using a
- Khoobi, Mehdi,Molaverdi, Fatemeh,Alipour, Masoumeh,Jafarpour, Farnaz,Foroumadi, Alireza,Shafiee, Abbas
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p. 11164 - 11168
(2014/01/06)
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- Palladium(II)-catalyzed direct carboxylation of alkenyl C-H bonds with CO2
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Pd-catalyzed direct carboxylation of alkenyl C-H bonds with carbon dioxide was realized for the first time. Treatment of 2-hydroxystyrenes and a catalytic amount of Pd(OAc)2 with Cs2CO3 under atmospheric pressure of CO2 afforded corresponding coumarins in good yield. Furthermore, isolation of the key alkenylpalladium intermediate via C-H bond cleavage was achieved. The reaction was proposed to undergo reversible nucleophilic addition of the alkenylpalladium intermediate to CO2.
- Sasano, Kota,Takaya, Jun,Iwasawa, Nobuharu
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p. 10954 - 10957
(2013/08/23)
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- Synthesis of substituted coumarins and 2-quinolinones by cycloisomerisation of (hydroxy/aminophenyl)propargyl alcohols
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A new cycloisomerization strategy for the synthesis of coumarins and quinolinones is described. The addition of ethoxyacetylide to 2-hydroxyacetophenones directly resulted in 4-substituted coumarins by 6-endo-dig cycloisomerisation of the intermediate 3-ethoxy-1-(2-hydroxyphenyl)- 2-propyn-1-ols. Under similar conditions, 2-aminoacetophenone produced 2-ethoxyquinoline, a masked quinolinone, which was converted into the quinolinone by acid treatment. N-Protected intermediate 8 was isolated and converted into the quinolinone [with In(OTf)3 or H2SO 4] or the 3-iodo-2-quinolinone (with I2 and H +).
- Sridhar Reddy, Maddi,Thirupathi, Nuligonda,Babu, Madala Hari
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p. 5803 - 5809
(2012/11/07)
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- Regioselective palladium-catalyzed direct cross-coupling of coumarins with simple arenes
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An efficient method for the C4-regiocontrolled C-H functionalization of coumarins to enable facile oxidative cross-couplings with simple arene components is disclosed.
- Min, Minsik,Hong, Sungwoo
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p. 9613 - 9615
(2012/10/29)
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- Palladium-catalyzed oxidative heck coupling reaction for direct synthesis of 4-arylcoumarins using coumarins and arylboronic acids
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An efficient protocol for the direct synthesis of 4-arylcoumarins via palladium-catalyzed oxidative Heck coupling reaction of coumarins and arylboronic acids was developed. 4-Arylcoumarins were obtained in moderate to excellent yields, and the reaction also showed tolerance toward functional groups such as hydro, methoxy, diethylamino, nitro, and chloro groups.
- Li, Yaming,Qi, Zisong,Wang, Huifeng,Fu, Xinmei,Duan, Chunying
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supporting information; experimental part
p. 2053 - 2057
(2012/04/04)
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- A facile route to flavone and neoflavone backbones via a regioselective palladium catalyzed oxidative Heck reaction
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A straightforward and atom-economical base-free palladium-catalyzed regioselective direct arylation of coumarins and chromenones is devised. This protocol is compatible with a wide variety of electron-donating and -withdrawing substituents and allows construction of various biologically important flavone and neoflavone backbones.
- Khoobi, Mehdi,Alipour, Masoumeh,Zarei, Samaneh,Jafarpour, Farnaz,Shafiee, Abbas
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supporting information; experimental part
p. 2985 - 2987
(2012/04/04)
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- A versatile palladium catalyst system for Suzuki-Miyaura coupling of alkenyl tosylates and mesylates
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A general and effective palladium system for Suzuki-Miyaura coupling of alkenyl electrophiles under mild reaction conditions is reported. With the Pd(OAc)2/CM-phos system, a variety of alkenyl tosylates are coupled well with ArB(OH)2. Moreover, the first successful examples of using alkenyl mesylates in alkenylation are also described.
- Wong, Pui Yu,Chow, Wing Kin,Chung, Kin Ho,So, Chau Ming,Lau, Chak Po,Kwong, Fuk Yee
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supporting information; experimental part
p. 8328 - 8330
(2011/09/14)
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- Improved synthesis of coumarins by iron(III)-catalyzed cascade reaction of propiolic acids and phenols
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The reaction of propiolic acids with phenols in the presence of FeClAgOTf catalyst proceeded efficiently in a mixed solvent of trifluoroacetic acid and 1,2-dichloroethane, and provided coumarins in good to high yields. This iron-catalyzed reaction offers a much-improved synthesis of coumarins. Thieme Stuttgart New York.
- Kutubi, Md. Shahajahan,Hashimoto, Takuya,Kitamura, Tsugio
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experimental part
p. 1283 - 1289
(2011/05/19)
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- Microwave-promoted, one-pot, solvent-free synthesis of 4-arylcoumarins from 2-hydroxybenzophenones
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4-Arylcoumarins are synthesized in very good yields through solvent-free microwave irradiation of 2-hydroxybenzophenones and alkyl malonate in the presence of DBU. The onepot synthesis is carried out with Knoevenagel condensation, intramolecular lactonization, and decarboxylation reactions. The method can be applied to a broad scope of neoflavonoids.
- Crecente-Campo, Jose,Vazquez-Tato, M. Pilar,Seijas, Julio A.
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experimental part
p. 4130 - 4135
(2010/09/18)
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- A novel synthesis of coumarins employing triphenyl(α-carboxymethylene)phosphorane imidazolide as a C-2 synthon
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A novel one-pot synthesis of coumarins via intramolecular Wittig cyclization from the reaction of phenolic compounds containing ortho-carbonyl group and triphenyl(α-carboxymethylene)phosphorane imidazolide is described.
- Upadhyay, Puspesh K.,Kumar, Pradeep
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scheme or table
p. 236 - 238
(2009/05/11)
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- Asymmetrie Conjugate reductions of coumarins. A new route to tolterodine and related coumarin derivatives
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"Chemical Equation Presented" The combination of catalytic amounts of [(R)-DTBM-SEGPHOS]CUH In the presence of stoichiometric DEMS (dlethoxymethylsllane) In toluene at room temperature leads to asymmetric reductions of 4-substituted coumarins. Several targets or their known precursors can be prepared In high yields and ee's, Including the muscarine receptor antagonist (R)-tolterodine.
- Gallagher, Brian D.,Taft, Benjamin R.,Lipshutz, Bruce H.
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supporting information; experimental part
p. 5374 - 5377
(2010/02/28)
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- N-heterocyclic carbene derived Nickel-Pincer complexes: Efficient and applicable catalysts for Suzuki-Miyaura coupling reactions of aryl/alkenyl tosylates and mesylates
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Catalytic activities of NHC-derived nickel-pincer complexes for the Suzuki-Miyaura coupling reactions of aryl/alkenyl to- sylates and mesylates are described. In the presence of a catalytic amount of nickelacycle 1a, a wide array of tosylates and mesylates reacted with several aryl- and alkenylboronic acids to afford the coupling products, generally in high yields. Fine tuning of the reaction conditions for each class of electrophiles was achieved only by choosing the appropriate reaction medium (DME for tosylates, dioxane for mesylates).
- Kuroda, Jun-Ichi,Inamoto, Kiyofumi,Hiroya, Kou,Doi, Takayuki
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scheme or table
p. 2251 - 2261
(2009/08/09)
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- Dually activated organo- and nano-cocatalyzed synthesis of coumarin derivatives
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A wide range of substituted coumarin derivatives were synthesized by refluxing in acetonitrile, ethyl acetoacetate, and ethyl benzoyl acetate with a wide range of structurally diverse phenol derivatives within a short reaction time with a catalytic combination of pyridine dicarboxylic acid as organocatalyst and nanocrystalline ZnO.
- Goswami, Papori
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experimental part
p. 2271 - 2278
(2009/12/03)
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- Microwave-promoted automated synthesis of a coumarin library
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A 30-membered library of coumarins has been synthesized in a microwave-assisted Pechmann reaction using neat trifluoroacetic acid both as an acidic reagent and a reaction medium. Alternatively, polymer-supported sulfonic acid Amberlyst-15 could also be employed to facilitate the formation of coumarins. The use of a specially-built microwave synthesizer with liquid handling tools rendered the automated synthesis of a coumarin library feasible.
- Katkevi?s,Kontijevskis,Mutule,Sūna
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p. 151 - 159
(2008/12/20)
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- Skeletal diversity construction via a branching synthetic strategy
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A branching synthetic strategy was used to efficiently generate structurally diverse scaffolds, which span a broad area of chemical descriptor space, and their biological activity against MRSA was demonstrated. The Royal Society of Chemistry 2006.
- Wyatt, Emma E.,Fergus, Suzanne,Galloway, Warren R. J. D.,Bender, Andreas,Fox, David J.,Plowright, Alleyn T.,Jessiman, Alan S.,Welch, Martin,Spring, David R.
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p. 3296 - 3298
(2008/09/19)
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- Short synthesis of cytotoxic 4-arylcoumarins
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A short synthesis of cytotoxic 4-arylcoumarins via condensation of phenols with cinnamic acids in the presence of CF3COOH, followed by dehydrogenation with DDQ, is described. Copyright Taylor & Francis Group, LLC.
- Rizzi, Eleonora,Dallavalle, Sabrina,Merlini, Lucio,Pratesi, Graziella,Zunino, Franco
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p. 1117 - 1122
(2007/10/03)
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- Synthesis of coumarins by Pt-catalyzed hydroarylation of propiolic acids with phenols
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Synthesis of coumarins from phenols and propiolic acids was examined by using a Pt catalyst such as PtCl2/AgOTf, K2PtCl4/AgOTf, and K2PtCl4/AgOAc. Propiolic acid reacted even with less reactive phenols in trifluoroacetic acid to give coumarins and dihydrocoumarins. In the case of substituted propiolic acids, phenylpropiolic acid and 2-octynoic acid, the reactions proceeded selectively to afford coumarins in good to high yields.
- Oyamada, Juzo,Kitamura, Tsugio
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p. 6918 - 6925
(2007/10/03)
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- K2PtCl4/AgOTf as a highly active catalyst for hydroarylation of propiolic acids with arenes
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A new and efficient K2PtCl4/AgOTf catalyst for the hydroarylation of propiolic acid was found. The hydroarylation of propiolic acids gave predominantly (Z)-cinnamic acid derivatives in high yields. The K2PtCl4/AgOTf catalyst showed a high activity to less reactive benzene. Copyright
- Oyamada, Juzo,Kitamura, Tsugio
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p. 1430 - 1431
(2007/10/03)
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- A convenient synthesis of coumarins by palladium(II)-catalyzed reaction of phenols with propiolic acids
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A direct route to coumarin derivatives from phenols and propiolic acids has been developed. Phenols react with propiolic acids in the presence of Pd(OAc)2 as a catalyst to give coumarins in good yields. The simple process occurs under mild conditions without any additives.
- Kotani, Masashi,Yamamoto, Kiyomi,Oyamada, Juzo,Fujiwara, Yuzo,Kitamura, Tsugio
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p. 1466 - 1470
(2007/10/03)
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- Pt(IV)-catalyzed cyclization of arene-alkyne substrates via C-H bond functionalization
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We herein report that PtCl4 has proven to be a hydroarylation catalyst with an efficiency and substrate scope superior to previously known methods. This catalyst demonstrated consistent performance with arene-yne substrates of diverse structural features, including propargyl ethers, propargylamines, and alkynoate esters, providing good to excellent yields of the 6-endo products (chromenes, dihydroquinolines, and coumarins). In contrast, Pt(II), Pd(II), and Ga(III) salts were shown to be sensitive to the substitution on the alkyne moiety. PtCl4 is compatible with both terminal and disubstituted alkynes, as well as with various functionalities on the arene ring, including methyl, methoxyl, hydroxyl, protected amine, and halide.
- Pastine, Stefan J.,Youn, So Won,Sames, Dalibor
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p. 8859 - 8868
(2007/10/03)
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- PdII-Catalyzed Reaction of Phenols with Propiolic Esters. A Single-Step Synthesis of Coumarins
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The intermolecular reaction of phenols with propiolic esters in TFA in the presence of a Pd(OAc)2 catalyst, affording coumarin derivatives, is described. An exclusive formation of 5,6,7-trimethoxy-4-phenylcoumarin was observed in the reaction of 3,4,5-trimethoxyphenol and ethyl phenylpropiolate with a catalytic amount of Pd(OAc)2. The reaction in the absence of Pd(OAc)2 did not give any coumarin at all. Coumarin derivatives were obtained in high yields in the cases of electron-rich phenols, such as 3,4-methylenedioxyphenol, 3-methoxyphenol, 2-naphthol, and 3,5-dimethoxyphenol. Furthermore, the reaction of some phenols with various 2-alkynoates or with diethyl acetylenedicarboxylate gave the corresponding coumarins in good-to-high yields.
- Kitamura, Tsugio,Yamamoto, Kiyomi,Kotani, Masashi,Oyamada, Juzo,Jia, Chengguo,Fujiwara, Yuzo
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p. 1889 - 1895
(2007/10/03)
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- Palladium-catalyzed cross-coupling reactions of 4-tosylcoumarin and arylboronic acids: Synthesis of 4-arylcoumarin compounds
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The palladium-catalyzed reaction between 4-tosylatecoumarin and arylboronic acids was investigated. This reaction provides an efficient approach to synthesize diversified 4-arylcoumarins in good yields.
- Wu, Jie,Wang, Lisha,Fathi, Reza,Yang, Zhen
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p. 4395 - 4397
(2007/10/03)
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- Direct synthesis of coumarins by Pd(II)-catalyzed reaction of alkoxyphenols and alkynoates
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Reaction of alkoxyphenols and alkynoates in the presence of a catalytic amount of Pd(OAc)2 in trifluoroacetic acid at room temperature gave coumarin derivatives in high yields. This procedure provides a convenient method for direct synthesis of coumarin derivatives under very mild conditions.
- Oyamada, Juzo,Jia, Chengguo,Fujiwara, Yuzo,Kitamura, Tsugio
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p. 380 - 381
(2007/10/03)
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- Stereoselective synthesis of (R)- and (S)-4-methoxydalbergione via asymmetric catalytic hydrogenation
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(Matrix presented) (R)-(+)-and (S)-(-)-4-methoxydalbergione were synthesized in seven steps with an enantiomeric excess of up to 95% using an asymmetric catalytic hydrogenation step with [Rh((S,S)-bdpp)(NBD)]CIO4 or [Rh((R,R)-bdpp)(NBD)]CIOsub
- Bissel, Philippe,Nazih, Abdesslame,Sablong, Rafael,Lepoittevin, Jean-Pierre
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p. 1283 - 1285
(2008/02/09)
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- Highly Efficient and Single Step Synthesis of 4-Phenylcoumarins and 3,4-Dihydro-4-phenylcoumarins over Montmorillonite K-10 Clay, under Microwave Irradiation
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A simple, elegant and one-pot synthesis of 3,4-dihydro-4-phenylcoumarins, 4-phenylcoumarins and their derivatives by making use of solid support, montmorillonite K-10 clay in conjunction with microwave irradiation is described.
- Singh, Jasvinder,Kaur, Jasamrit,Nayyar, Sandeep,Kad, Goverdhan L.
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p. 280 - 281
(2007/10/03)
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