- Free radical scavenging and α-glucosidase inhibitory activity of (E)-methyl/ethyl-3-(2-hydroxyphenyl)acrylates
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(E)-Methyl/ethyl-3-(2-hydroxyphenyl)acrylates 3a-x have been prepared by the reaction of salicylaldehydes 1a-l with Wittig reagents such as methyl (triphenylphosphoranylidene)acetate 2a and ethyl (triphenylphosphoranylidene)acetate 2b in dry DCM at room t
- Harikrishna, G.,Hariprasad, K. Siva,Raju, B. China,Tiwari, A. K.,Zehra, A.
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p. 111 - 116
(2021/09/28)
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- Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides
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Herein, we describe a simple general method for the synthesis of 4-arylcoumarins using pentavalent organoantimony compounds. The reactions of 3-(2-hydroxyaryl)acrylates with triarylantimony difluorides in the presence of Pd(OAc)2 (10 mol-%) and 2,2'-bipyridyl (10 mol-%) at 80 °C under aerobic conditions afforded 4-arylcoumarins in good-to-excellent yields. This protocol involves a cascade oxidative Heck-type arylation followed by cyclization, with all the aryl groups in the triarylantimony difluoride transferred to the coupling products. Triarylantimony difluorides resulted in better outcomes than those obtained with other pentavalent organoantimony or bismuth compounds.
- Kitamura, Yuki,Matsumura, Mio,Kato, Yukari,Murata, Yuki,Yasuike, Shuji
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supporting information
p. 1652 - 1657
(2020/03/05)
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- Late-Stage Direct o-Alkenylation of Phenols by PdII-Catalyzed C?H Functionalization
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o-Alkenylation of unprotected phenols has been developed by direct C?H functionalization catalyzed by PdII. This work features phenol group as a directing group and realizes highly site-selective C?H bond functionalization of phenols to achieve the corresponding products in moderate to excellent yields at 60 °C. The advantages of this reaction include unprecedented C?H functionalization using phenol as a directing group, high regioselectivity, good substrate scope, mild reaction conditions, and high efficiency. To the best of our knowledge, this is the first example of a regioselective C?H alkenylation of unprotected phenols utilizing phenolic hydroxyl group as a directing group. The alkenylation of unprotected tyrosine and intramolecular cyclization are also successfully carried out under this catalytic system in good yields. Furthermore, this novel method enables a late-stage modification of complex phenol-containing bioactive molecules toward a diversity-oriented drug discovery.
- Dou, Yandong,Kenry,Liu, Jiang,Jiang, Jianze,Zhu, Qing
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supporting information
p. 6896 - 6901
(2019/05/07)
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- Rh-Catalyzed Deformylative Coupling of Salicylaldehydes with Acrylates and Acrylamides
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An unprecedented deformylative coupling of salicylaldehydes to acrylates and acrylamides under Rh-catalyzed conditions is reported. These deformylative couplings afforded o-hydroxycinnamates and o-hydroxycinnamamides with broad functional group tolerance and high chemoselectivity under milder reaction conditions.
- Rao, Maddali L.N.,Ramakrishna, Boddu S.
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supporting information
p. 5677 - 5683
(2019/05/01)
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- One-Pot Synthesis of Functionalized Fused Furans via a BODIPY-Catalyzed Domino Photooxygenation
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Six-membered ring fused furans containing a tetrasubstituted tertiary carbon were prepared in an unprecedented one-pot BODIPY-catalyzed domino photooxygenation/reduction process. A series of functionalized furans was synthesized from readily available 2-alkenylphenols and mechanistic studies were performed to account for the domino photosensitized oxygenation.
- Mauger, Audrey,Farjon, Jonathan,Nun, Pierrick,Coeffard, Vincent
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supporting information
p. 4790 - 4793
(2018/03/21)
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- Palladium-catalyzed diastereoselective synthesis of β,β-diarylpropionic acid derivatives and its application to the total synthesis of (R)-tolterodine and the enantiomer of a key intermediate for MK-8718
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Palladium-catalyzed diastereoselective synthesis of optically active β,β-diarylpropionic acid derivatives employing 4-(tert-butyl)oxazolidin-2-one as the chiral auxiliary under an air atmosphere in excellent yields with high diastereoselectivity is reported. The catalytic system is applied to the total synthesis of (R)-tolterodine and the enantiomer of a key intermediate for MK-8718.
- Zhi, Wubin,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
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supporting information
p. 537 - 540
(2018/01/17)
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- Coumarins from free ortho -hydroxy cinnamates by Heck-Matsuda arylations: A scalable total synthesis of (R)-tolterodine
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Free ortho-hydroxy cinnamate ester derivatives are evaluated in the synthesis of structurally diverse 4-aryl-coumarins via a tandem Heck-Matsuda cyclization reaction. Free phenolic groups were considered incompatible with such a reaction, which usually provide the corresponding diazo dyes. A concise and scalable route employing a ligand-free, Pd-catalyzed Heck-Matsuda arylation under aerobic conditions for the preparation of (R)-Tolterodine in high overall yield and ee is also presented.
- Barancelli, Daniela A.,Salles, Airton G.,Taylor, Jason G.,Correia, Carlos Roque D.
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supporting information
p. 6036 - 6039
(2013/02/23)
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- Rhodium-catalyzed domino conjugate addition-cyclization reactions for the synthesis of a variety of N- and O-heterocycles: Arylboroxines as effective carbon nucleophiles
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Facile and efficient Rh(I)-catalyzed domino conjugate addition-cyclization reactions of olefins bearing two electrophilic sites and a pendant nucleophile with organoboroxines have been developed to afford a variety of N- and O-heterocycles, such as 3,4-dihydroquinolin-2(1H)-ones, 3,4-dihydrocoumarins, and pyrrolidin-2-ones, which constitute important motifs in biologically active natural and synthetic organic compounds.
- Park, Ja Ock,Youn, So Won
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supporting information; experimental part
p. 2258 - 2261
(2010/07/17)
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- SULFONAMIDE DERIVATIVE HAVING PGD2 RECEPTOR ANTAGONISTIC ACTIVITY
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A sulfonamide derivative having DP receptor antagonistic activity; and a medicinal composition and a therapeutic agent for allergic diseases which each contains the compound as an active ingredient. The derivative is a compound represented by the general formula (II): (II) (wherein ring A is an aromatic carbocycle, etc.; ring B is a nitrogenous nonaromatic heterocycle, etc.; ring C is an aromatic carbocycle, etc.; R1 is carboxy, etc.; R2's each independently is halogeno, etc.; R3 is optionally substituted alkyloxy, etc.; R4's each independently is halogeno, etc.; R5's each independently is optionally substituted alkyl, etc.; M is sulfonyl, etc.; Y is a single bond, etc.; L1 is a single bond, etc.; L2 is a single bond, etc.; k is 0, 1, 2, 3, or 4; n is 0, 1, or 2; and q is 0, 1, 2, or 3, provided that, for example, a) when ring B is a 6-membered nitrogenous heterocycle containing one or two nitrogen atoms and ring C is a benzene ring, then k is not 0), a pharmaceutically acceptable salt of the compound, or a hydrate of either.
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Page/Page column 112-113
(2010/11/26)
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- An efficient route from coumarins to highly functionalized N-phenyl-2-quinolinones via Buchwald-Hartwig amination
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Multiple substituted N-phenyl-2-quinolinones were obtained in a convenient four-step route from a variety of commercially available coumarins, utilizing customised Buchwald-Hartwig amination protocols for the key reaction. Whereas simple aminolysis of cou
- Ullrich, Thomas,Giraud, Francis
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p. 4207 - 4211
(2007/10/03)
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- Aryl-acrylic acid esters
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The acrylic acid esters of Formula I are useful for the delivery of organoleptic compounds, especially for flavors, fragrances, masking agents and antimicrobial compounds. They can also deliver fluorescent whitening agents.
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