6971-52-4Relevant articles and documents
Regiospecific and highly stereoselective formation of benzisochroman-6,9-quinones. Synthesis of (±)-ventilagone and (±)-ventiloquinone H
Blouin,Beland,Brassard
, p. 1466 - 1471 (1990)
An approach known to give regiospecific cycloadditions over a wide range of substrates has been applied to the synthesis of (±)-ventilagone and (±)-ventiloquinone H using a novel, electron-rich heterocyclic diene. The strategy provides for the sole format
Derivatives of m-Guaiacol, Their Preparation and Their Uses
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Paragraph 0125; 0141, (2021/11/05)
The invention concerns derivatives of m-guaiacol, their preparation and their uses as biocides, in particular as antibacterials or disinfectants.
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.
A scalable synthesis of CE-157119 HCl Salt, an SRI/5-HT2A antagonist
Tao, Yong,Widlicka, Daniel W.,Hill, Paul D.,Couturier, Michel,Young, Gregory R.
, p. 1805 - 1810 (2013/01/15)
A scalable synthesis of CE-157119 HCl salt (1), an SRI/5-HT2A antagonist, was developed via the regioselective SNAr etherification between a phenol and an N-methylamide. This early development route shortened the original 5-step synt
IMIDAZOLIDINEDIONE DERIVATIVES
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, (2011/06/26)
The invention provides a compound of formula (Ia), and pharmaceutically acceptable salts thereof. The invention also provides use of the compounds or salts as modulators of Kv3.1 and/or Kv3.2, and in the treatment of diseases or disorders where a modulator of Kv3.1 and/or Kv3.2 is required, such as depression and mood disorders, hearing disorders, schizopherenea, substance abuse disorders, sleep disorders or epilepsy.
Microwave-assisted cleavage of aryl methyl ethers with lithium thioethoxide (LiSEt)
Cvengro?, Ján,Neufeind, Stefan,Becker, Anne,Schmalz, Hans-Günther
experimental part, p. 1993 - 1998 (2009/04/07)
Lithium thioethoxide (LiSEt), a white solid easily prepared from EtSH and n-BuLi in hexane, was identified as a highly efficient reagent for the cleavage (O-demethylation) of aryl methyl ethers, i.e. methyl-protected phenols. Of particular synthetic value are applications in the double deprotection of 1,2-dimethoxyarenes (to give catechols) and in the selective monodeprotection of di- and trimethoxyarenes. The thermal reactions, which are usually performed in DMF as a solvent, can be greatly accelerated through microwave irradiation. In this case, the monodemethylated products are usually formed in high (80-99%) yield within only 15 minutes.
SYNTHESIS OF THERAPEUTIC DIPHENYL ETHERS
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Page/Page column 3-4; 6, (2008/06/13)
This invention is directed to a method of synthesizing compounds of Formula I and to intermediates useful in the synthesis of compounds of Formula I wherein X, Y, R1, R2, R3, and R4 are as defined herein above.
Lewis Acid-Directed Reactions of Quinones with Styrenyl Systems: The Case of 2-Methoxy-3-methyl-1,4-benzoquinone
Engler, Thomas A.,Iyengar, Rajesh
, p. 1929 - 1934 (2007/10/03)
Reactions of 2-methoxy-3-methyl-1,4-benzoquinone with various (E)-1-propenylbenzenes promoted by 1 equiv of Ti(IV), as a 1:1 mixture of TiCl4-Ti(O-i-Pr)4, produce rel-(1S,6R,7R,8R)-8-aryl-4,7-dimethyl-3-methoxybicyclo[4.2.0]oct-3-ene-2,5- diones 3 and trans-2-aryl-3,7-dimethyl-6-methoxy-2,3-dihydro-5-benzofuranols 5 as the major products. Reactions promoted by 2 equiv of Ti(IV) as a 1:1 mixture of TiCl4-Ti(O-i-Pr)4 or 1 equiv of either TiCl4, SnCl4, or BF3·OEt2 give regioisomeric rel-(1R,6S,7A,8R)-7-aryl-4,8-dimethyl-3-methoxybicyclo[4.2.0]oct-3-ene-2,5- diones (4) and/or trans-2-aryl-3,6-dimethyl-7-methoxy-2,3-dihydro-5-benzofuranols (6). A mechanism involving regioselective coordination of the various Lewis acids to the quinone is used to explain the formation of the products. These reactions demonstrate the effective regiocontrol exerted over the reactions by the nature of the Lewis acid promoters. Cyclobutanes 3 and 4 cleanly undergo rearrangement to the corresponding benzofuranols 5 and 6 on treatment with protic acid. In contrast, reactions of 2-methoxy-1,4-benzoquinone promoted by either BF3·OEt2 or Ti(IV), as 1 equiv or excess amounts of TiCl4 or 1:1 TiCl4-Ti(O-i-Pr)4, all afford the same regioisomeric products, i.e., rel-(1S,6R,7R,8R)-8-aryl-7-methyl-3-methoxybicyclo[4.2.0]oct-3-ene-2,5-dione 25 and/or trans-2-aryl-3-methyl-6-meth-oxy-2,3-dihydro-5-benzofuranol 27.
Regioselectivity in the Reductive Cleavage of Pyrogallol Derivatives: Reductive Electrophilic Substitution of Acetals of 2,3-Dimethoxyphenol
Azzena, Ugo,Melloni, Giovanni,Pisano, Luisa
, p. 261 - 266 (2007/10/02)
Acetals of 2,3-dimethoxyphenol were used as the starting materials for the transformation of 1,2,3-trioxygenated benzenes into various 1-oxygenated-2,3-dicarbon-substituted benzenes, via regioselective reductive electrophilic substitution of the 2-methoxy
Ultrasound-promoted synthesis of substituted phenanthrene-1,4-quinones; the structure of plectranthon D
Zhang, Zhao-Rong,Flachsmann, Felix,Moghaddam, Firouz Matloubi,Rueedi, Peter
, p. 2153 - 2156 (2007/10/02)
A series of tanshinone-type diterpenoids was prepared by ultrasound-promoted and Lewis acid catalyzed, highly regioselective cycloadditions of styrenes with substituted 1,4-benzoquinones as the key step.