37055-80-4Relevant academic research and scientific papers
Synthesis of aryl-substituted 2-methoxyphenol derivatives from maltol-derived oxidopyrylium cycloadducts through an acid-mediated ring contraction cascade
Bejcek, Lauren P.,Murelli, Ryan P.
, p. 3203 - 3205 (2020)
Oxidopyrylium cycloadducts derived from maltol and aryl acetylenes undergo acid-mediated rearrangements to generate aryl-substituted 2-methoxyphenol (guaiacol) derivatives. Specifically, the cycloadducts react with boron trichloride to form 2-methoxy-5-ar
Copper-catalyzed meta-selective arylation of phenol derivatives: An easy access to m-aryl phenols
Maraswami, Manikantha,Hirao, Hajime,Loh, Teck-Peng
, p. 2302 - 2309 (2021/02/20)
Achieving selective meta-functionalization of phenols is a significant challenge. Accessing such compounds generally needs elevated temperature or incorporation of complex templates. Here, we report a general approach to achieve meta-arylated phenols with a simple and common directing group. This coppercatalyzed protocol proceeds with complete meta-selectivity and tolerates a variety of functional groups in both coupling partners. Computational studies have revealed that the reaction proceeded via a Heck-like pathway.
Tuning the Reactivity of Peroxo Anhydrides for Aromatic C-H Bond Oxidation
Pilevar, Afsaneh,Hosseini, Abolfazl,?ekutor, Marina,Hausmann, Heike,Becker, Jonathan,Turke, Kevin,Schreiner, Peter R.
, p. 10070 - 10079 (2018/09/06)
Phenol moieties are key structural motifs in many areas of chemical research from polymers to pharmaceuticals. Herein, we report on the design and use of a structurally demanding cyclic peroxide (spiro[bicyclo[2.2.1]heptane-2,4′-[1,2]dioxolane]-3′,5′-dione, P4) for the direct hydroxylation of aromatic substrates. The new peroxide benefits from high thermal stability and can be synthesized from readily available starting materials. The aromatic C-H oxidation using P4 exhibits generally good yields (up to 96%) and appreciable regioselectivities.
Direct Hydroxylation and Amination of Arenes via Deprotonative Cupration
Tezuka, Noriyuki,Shimojo, Kohei,Hirano, Keiichi,Komagawa, Shinsuke,Yoshida, Kengo,Wang, Chao,Miyamoto, Kazunori,Saito, Tatsuo,Takita, Ryo,Uchiyama, Masanobu
supporting information, p. 9166 - 9171 (2016/08/05)
Deprotonative directed ortho cupration of aromatic/heteroaromatic C-H bond and subsequent oxidation with t-BuOOH furnished functionalized phenols in high yields with high regio- and chemoselectivity. DFT calculations revealed that this hydroxylation reaction proceeds via a copper (I → III → I) redox mechanism. Application of this reaction to aromatic C-H amination using BnONH2 efficiently afforded the corresponding primary anilines. These reactions show broad scope and good functional group compatibility. Catalytic versions of these transformations are also demonstrated.
WB4101-related compounds: New, subtype-selective α1- adrenoreceptor antagonists (or inverse agonists?)
Pallavicini, Marco,Budriesi, Roberta,Fumagalli, Laura,Ioan, Pierfranco,Chiarini, Alberto,Bolchi, Cristiano,Ugenti, Maria Paola,Colleoni, Simona,Gobbi, Marco,Valoti, Ermanno
, p. 7140 - 7149 (2007/10/03)
Our previous structure-affinity relationship study had considered the enantiomers of the naphthodioxane, tetrahydronaphthodioxane, and 2-methoxy-1-naphthoxy analogues (compounds 1, 3, and 2, respectively) of 2-(2,6-dimethoxyphenoxyethylaminomethyl)-1,4-be
A new entry to the synthesis of 1,2-benzenediol congeners
Ozaki,Oshio,Ohsuga,Kaburagi,Sung,Kim
, p. 1132 - 1136 (2007/10/02)
1,2-Benzenediols were synthesized via 1,1-bis(ethylthio)-3-cyclohexen-2-one derivatives, which were prepared by condensation of 1,1-bis(ethylthio)-2-propanone with Mannich bases. Regioselective preparation of their monoethers was also achieved.
A NEW ENTRY TO 1,2-BENZENEDIOL CONGENERS
Ozaki, Yutaka,Oshio, Ikumi,Kim, Sang-Won
, p. 1434 - 1436 (2007/10/02)
1,2-Benzenediols and their monoethers were efficiently prepared from α,α-bis(ethylthio)cyclohexenones which were constructed by the C3+C3 annulation of 1,1-bis(ethylthio)propan-2-one and the Mannich bases. KEYWORDS 1,2-benzenediol; aromatic synthesis; annulation; aromatic compound; acetal
REGIOSELECTIVITY OF NUCLEOPHILIC AROMATIC PHOTOSUBSTITUTION IN THE BIPHENYL SERIES. PHOTOHYDROLYSIS OF SOME DIMETHOXYNITROBIPHENYLS
Urban, Jan,Kuzmic, Petr,Saman, David,Soucek, Milan
, p. 2482 - 2491 (2007/10/02)
Anaerobic photolysis of dimethoxynitrobiphenyls IIIa-VIa in aqueous alkaline tert-butanol gave products of nucleophilic photodubstitution of methoxyl by hydroxide anion, while the dimethoxybiphenyls Ia and IIa were found unreactive.Regioselectivity of the reaction was examined in view of a possible "extended meta activation" by the nitro group.The most reactive substrate IIIa gives both C-3 and C-4 substitution products with an unsubstantial preference for the latter, which opposes the "extended meta selectivity" rule.All of the other compounds obey the rule, and 3,4-dimethoxy-3'-nitrobiphenyl (IVa) even displayed absolute selectivity by yielding C-3 substituted compound as the only product. 2,5-Dimethoxy substituted compounds underwent photosubstitution with much lower quantum yields than their 3,4-substituted counterparts, most probably due to some steric hindrance of conjugation.Similarly, 3-nitro-substituted biphenyls exhibited much lower overall reactivity than 4-nitro derivatives.
