- Synthesis of Bicyclo[1.1.1]pentane Bioisosteres of Internal Alkynes and para-Disubstituted Benzenes from [1.1.1]Propellane
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We report a general preparation of arylated bicyclo[1.1.1]pentanes through the opening of [1.1.1]propellane with various arylmagnesium halides. After transmetalation with ZnCl2 and Negishi cross-coupling with aryl and heteroaryl halides, bis-arylated bicyclo[1.1.1]pentanes are obtained. These bis-arylated bicyclo[1.1.1]pentanes may be considered as bioisosteres of internal alkynes. Bioisosteres of tazarotene and the metabotropic glutamate receptor 5 (mGluR5) antagonist 2-methyl-6-(phenylethynyl)pyridine were prepared and their physicochemical properties were evaluated.
- Makarov, Ilya S.,Brocklehurst, Cara E.,Karaghiosoff, Konstantin,Koch, Guido,Knochel, Paul
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- Strain-release arylations for the bis-functionalization of azetidines
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The addition of nucleophilic organometallic species onto in situ generated azabicyclobutanes enables the selective formation of 3-arylated azetidine intermediates through strain-release. Single pot strategies were further developed for the N-arylation of resulting azetidines, employing either SNAr reactions or Buchwald-Hartwig couplings.
- Aicher, Julian,Apaloo-Messan, Kodjo-Edmond,Didier, Dorian,Jiang, Dongfang,Ni?l, Benedikt,Reiners, Felix,Shahbaz, Muhammad,Trauner, Florian
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p. 2564 - 2567
(2022/03/03)
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- Br?nsted Acid-Catalyzed Regioselective Hydrothiolation of Dienes: Solvent-Controlled Divergent Synthesis of Sulfides
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A Br?nsted acid-catalyzed 1,4-addition hydrothiolation of branched 1,3-dienes was explored for the first time. A solvent-controlled divergent synthesis of sulfides is also disclosed. Use of acetonitrile as a solvent gave allylic sulfides as hydrothiolation products, while thiochromane derivatives (hydrothiolation/Friedel-Crafts products) were obtained using dichloromethane as the solvent. The origin of the regioselectivity of hydrothiolation was explored through density functional theory calculations.
- Chen, Zhi-Min,Huang, Jie,Ji, Kai,Ke, Hua,Li, Zi-Hao,Lu, Ka
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supporting information
p. 8028 - 8032
(2021/10/30)
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- One-pot synthesis of 6-bromo-4,4-dimethylthiochroman
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One-pot synthesis of 6-bromo-4,4-dimethylthiochroman from bromobenzene is reported. The crucial connection between the three steps is that the byproducts in the first two steps are used as the catalyst in the third step. Compared with the previous route, this approach is of low consumption and low pollution.
- Zhou, Shaodong,Liao, Zutai,Yuan, Jixin,Qian, Chao,Chen, Xinzhi
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p. 4121 - 4125
(2013/11/19)
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- SPIROXAZOLIDINONE COMPOUNDS
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Substituted spirocyclic amines of structural formula (I) are selective antagonists of the somatostatin subtype receptor 5 (SSTR5) and are useful for the treatment, control or prevention of disorders responsive to antagonism of SSTR5, such as Type 2 diabetes, insulin resistance, lipid disorders, obesity, atherosclerosis, Metabolic Syndrome, depression, and anxiety.
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Page/Page column 187-188
(2012/03/11)
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- Process for the preparation of Tazarotene
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Tazarotene is prepared by deoxygenation of the corresponding S-oxide, in turn obtained according to two alternative synthetic pathways.
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Page/Page column 3
(2010/11/23)
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- A process for the preparation of tazarotene
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Tazarotene is prepared by deoxygenation of the corresponding S-oxide, in turn obtained according to two alternative synthetic pathways.
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Page/Page column 5
(2010/11/23)
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- Aromatic polycyclic retinoid-type derivatives, method for preparing same, and use thereof for making pharmaceutical and cosmetic compositions
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Novel aromatic polycyclic retinoid-type derivatives of general formula (I), wherein groupings R3and R4attached to the double bond between carbons 11 and 12 are cis groupings, and pharmaceutical and cosmetic compositions containing same, are disclosed.
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- Biphenyl derivatives substituted by an aromatic or heteroaromatic radical and pharamaceutical and cosmetic compositions containing same
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“Biphenyl derivatives substituted with an aromatic or heteroaromatic radical, and pharmaceutical and cosmetic compositions containing them” in which: Ar represents an aromatic or a heteroaromatic radical optionally substituted, in particular, with an alkyl or a carboxyl group, R2and R3represent, in particular, H or alkyl, or R2and R3, taken together, form a 5- or 6-membered ring, R4and R5represent, in particular, H or halogen, R6represents, in particular, H or lower alkyl, and the salts of the compounds of formula (I). These compounds can be used in particular in the treatment of dermatological complaints associated with a keratinization disorder, and for combating ageing of the skin.
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- PYRIDYLPYRROLE DERIVATIVES
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Object: to provide compounds having an inhibitory effect on the production of inflammatory cytokines. Constitution: compounds having general formula (I), pharmacologically acceptable salts thereof or derivatives of the same, wherein A: single bond, oxygen
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- Process for preparing 4,4-dialkyl-6-halo-chromans or thiochromans useful as pharmaceutical intermediates
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A process of preparing intermediates useful in making compounds with retinoic acid-like activity is disclosed. The intermediates are halogenated chromans and thiochromans of the formula shown below and are prepared by the alkylation of a phenol or thiophe
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- Thiochroman esters of phenols and terephthallates having retinoid-like activity
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Compounds of formula I STR1 in which: the R groups are independently hydrogen or lower alkyl; one of A and B is O or S and the other is --C(O)--, A being attached to the thiochroman ring at the 6 or 7-position; n is 0-5; and Z is H, an acid or acid derivative, an alcohol or alcohol derivative, acetal or acetal derivative or ketone or ketone derivative, or a pharmaceutically acceptable salt, have retinoid-like activity.
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- Thiochroman esters of phenols and terephthallates having retinoid-like activity
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Compounds of formula I STR1 in which: the R groups are independently hydrogen or lower alkyl; one of A and B is O or S and the other is --C(O)--, A being attached to the thiochroman ring at the 6 or 7-position;n is 0-5; andZ is H, an acid or acid derivative, an alcohol or alcohol derivative, acetal or acetal derivative or ketone or ketone derivative, or a pharmaceutically acceptable salt, have retinoid-like activity.
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