175647-90-2Relevant academic research and scientific papers
Free radical scavenging and α-glucosidase inhibitory activity of (E)-methyl/ethyl-3-(2-hydroxyphenyl)acrylates
Harikrishna, G.,Hariprasad, K. Siva,Raju, B. China,Tiwari, A. K.,Zehra, A.
, p. 111 - 116 (2021/09/28)
(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
Cascade Synthesis of 4-Arylcoumarins: Pd-Catalyzed Arylations and Cyclizations with (E)-Ethyl 3-(2-Hydroxyaryl)acrylates and Triarylantimony Difluorides
Kitamura, Yuki,Matsumura, Mio,Kato, Yukari,Murata, Yuki,Yasuike, Shuji
supporting information, p. 1652 - 1657 (2020/03/05)
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.
Late-Stage Direct o-Alkenylation of Phenols by PdII-Catalyzed C?H Functionalization
Dou, Yandong,Kenry,Liu, Jiang,Jiang, Jianze,Zhu, Qing
supporting information, p. 6896 - 6901 (2019/05/07)
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.
Rh-Catalyzed Deformylative Coupling of Salicylaldehydes with Acrylates and Acrylamides
Rao, Maddali L.N.,Ramakrishna, Boddu S.
supporting information, p. 5677 - 5683 (2019/05/01)
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.
One-Pot Synthesis of Functionalized Fused Furans via a BODIPY-Catalyzed Domino Photooxygenation
Mauger, Audrey,Farjon, Jonathan,Nun, Pierrick,Coeffard, Vincent
supporting information, p. 4790 - 4793 (2018/03/21)
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.
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
Zhi, Wubin,Li, Jingya,Zou, Dapeng,Wu, Yangjie,Wu, Yusheng
supporting information, p. 537 - 540 (2018/01/17)
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.
Coumarins from free ortho -hydroxy cinnamates by Heck-Matsuda arylations: A scalable total synthesis of (R)-tolterodine
Barancelli, Daniela A.,Salles, Airton G.,Taylor, Jason G.,Correia, Carlos Roque D.
supporting information, p. 6036 - 6039 (2013/02/23)
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.
Rhodium-catalyzed domino conjugate addition-cyclization reactions for the synthesis of a variety of N- and O-heterocycles: Arylboroxines as effective carbon nucleophiles
Park, Ja Ock,Youn, So Won
supporting information; experimental part, p. 2258 - 2261 (2010/07/17)
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.
SULFONAMIDE DERIVATIVE HAVING PGD2 RECEPTOR ANTAGONISTIC ACTIVITY
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Page/Page column 112-113, (2010/11/26)
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.
An efficient route from coumarins to highly functionalized N-phenyl-2-quinolinones via Buchwald-Hartwig amination
Ullrich, Thomas,Giraud, Francis
, p. 4207 - 4211 (2007/10/03)
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
