- Synthesis and characterisation of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives. X-ray structure of 3-SF5-C6H4-COOH
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The high yield synthesis of 3- and 4-(pentafluorosulfanyl)benzoic acid derivatives is described starting from the NO2-derivatives, which are reduced to the corresponding anilines. Then the NH2- group is converted to bromide and subsequently to the HC{double bond, long}O moiety. The benzaldeydes are then oxidised to the corresponding benzoic acids. The X-ray structure of 3-SF5-C6H4-COOH is also reported.
- Zarantonello,Guerrato,Ugel,Bertani,Benetollo,Milani,Venzo,Zaggia
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Read Online
- Preparation of (Pentafluorosulfanyl)benzenes by Direct Fluorination of Diaryldisulfides: Synthetic Approach and Mechanistic Aspects
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Direct fluorination of ortho-, meta- and para-substituted aromatic thiols and disulfides using elemental fluorine afforded substituted (pentafluorosulfanyl)benzenes. This work thus represents the first study of the scope and limitation of direct fluorination for the synthesis of new SF5-containing building blocks. Fluorinations in batch and flow modes were compared. A comprehensive computational study was carried out employing density functional and wave function methods to elucidate the reaction mechanism of the transformation of ArSF3 into ArSF5. Eliminating various nonradical pathways, it has been shown that the reaction proceeds by a radical mechanism, initiated by the attack of the F. on the ArSF3 moiety, propagated via an almost barrierless F2+ArSF4 .→ArSF5+F. step and terminated by the ArSF4 .+F.→ArSF5. Most of the calculated data are in very good agreement with experimental observations concerning the ortho-substituent effect on the reaction rates and yields.
- Ajenjo, Javier,Klepetá?ová, Blanka,Greenhall, Martin,Bím, Daniel,Culka, Martin,Rulí?ek, Lubomír,Beier, Petr
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supporting information
p. 11375 - 11382
(2019/08/20)
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- METHOD FOR PRODUCING NITROGEN-CONTAINING PENTAFLUOROSULFANYLBENZENE COMPOUND
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A method for producing a nitrogen-containing pentafluorosulfanylbenzene compound of formula (2a) or (2b): (wherein R1 a hydrogen atom or a hydrocarbon group; Z is an aryl group linked to a carbonyl group; Y is a group of formula (Y1), (Y2), (Y3), or (Y4); R2 is a hydrogen atom or a hydrocarbon group) the method comprising reacting a halogeno-pentafluorosulfanylbenzene compound of formula (1) with a nitrogenous nucleophile: (wherein X is a halogen atom; n is an integer of 1 to 5; R1 is as defined above).
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Paragraph 0098; 0099; 0100; 0101
(2018/01/11)
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- The pentafluorosulfanyl group in cannabinoid receptor ligands: Synthesis and comparison with trifluoromethyl and tert-butyl analogues
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An array of cannabinoid ligands, bearing meta- and para-substituted pentafluorosulfanyl (SF5) aniline groups in position 3 of the pyrazole ring, was efficiently synthesised and compared with the exact trifluoromethyl and tert-butyl analogues. In general, the SF5 substituted ligands showed higher lipophilicity (i.e. logP values) than the CF3 counterparts and lower lipophilicity than the tert-butyl ones. In terms of pharmacological activity, SF5 pyrazoles generally showed slightly higher or equivalent CB1 receptor affinity (Ki), always in the nanomolar range, and selectivity towards the CB2 relative to both CF3 and tert-butyl analogues. Functional β-arrestin recruitment assays were used to determine equilibrium dissociation constants (Kb) and showed that all of the tested SF 5 and CF3 compounds are CB1 neutral antagonists. These results confirm the possibility of successfully using an aromatic SF5 group as a stable, synthetically accessible and effective bioisosteric analogue of the electron-withdrawing CF3 group, and possibly also of bulky aliphatic groups, for drug discovery and development applications. This journal is the Partner Organisations 2014.
- Altomonte, Stefano,Baillie, Gemma L.,Ross, Ruth A.,Riley, Jennifer,Zanda, Matteo
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p. 20164 - 20176
(2014/06/09)
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- Ir-catalyzed preparation of SF5-substituted potassium aryl trifluoroborates via C-H borylation and their application in the Suzuki-Miyaura reaction
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The preparation of new pentafluorosulfanyl-substituted potassium aryltrifluoroborates via Ir-catalyzed C-H borylation is reported. The utility of these novel building blocks was demonstrated in the Suzuki-Miyaura cross-coupling reaction, giving access to
- Joliton, Adrien,Carreira, Erick M.
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supporting information
p. 5147 - 5149
(2013/11/06)
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- Synthesis of pentafluorosulfanyl-containing indoles and oxindoles
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Vicarious nucleophilic substitution (VNS) of 3- and 4- nitro(pentafluorosulfanyl)benzenes with phenoxyacetonitrile followed by catalytic hydrogenation provided a two-step, atom-economical synthetic route to 6- and 5-(pentafluoro-sulfanyl)-1H-indoles. The
- Iakobson, George,Po?ta, Martin,Beier, Petr
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p. 855 - 859
(2013/05/22)
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- Preparations and reactions of SF5-substituted aryl and heteroaryl derivatives via Mg and Zn organometallics
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Polyfunctional SF5-substituted cycles: Several organometallic sequences using zinc, copper, and magnesium intermediates were developed to prepare a broad range of SF5-substituted aromatic and heterocyclic compounds of potential interest for pharmaceutical applications. Copyright
- Frischmuth, Annette,Unsinn, Andreas,Groll, Klaus,Stadtmueller, Heinz,Knochel, Paul
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supporting information; experimental part
p. 10234 - 10238
(2012/10/08)
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- Substituted imidazoline-2,4-diones, process for preparation thereof, medicaments comprising these compounds and use thereof
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The invention relates to compounds of formula (I) wherein the groups R and R′, A, D, E, G, L, p and R1 to R10 have the stated meanings and to their physiologically compatible salts. Said compounds are suitable, for example, as anti-obesity drugs.
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Page/Page column 78
(2011/05/16)
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- Arylaminoaryl-alkyl-substituted imidazolidine-2,4-diones, process for preparing them, medicaments comprising these compounds, and their use
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This invention relates to arylaminoaryl-alkyl-substituted imidazolidone-2,4-diones of formula (I) and also to their physiologically tolerated salts: Wherein R, R′, R1 to R10, A, D, E, G, L and p are as defined herein. The invention also relates to processes for preparing them, pharmaceutical compositions comprising them and their therapeutic use. The compounds are suitable, for example, as anti-obesity drugs and for treating cardiometabolic syndrome.
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Page/Page column 48
(2009/09/07)
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- A new synthesis of pentafluorosulfanylbenzene
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(Equation Presented) A new and convenient three-step synthesis of pentafluorosulfanylbenzene from 1,4-cyclohexadiene with an overall yield of >70% is reported along with a number of derivatization reactions.
- Sergeeva, Tatiana A.,Dolbier Jr., William R.
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p. 2417 - 2419
(2007/10/03)
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- Synthesis of some arylsulfur pentafluoride pesticides and their relative activities compared to the trifluoromethyl analogues
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Examples of pesticides containing an arylsulfur pentafluoride group were made and their biological activities compared to the corresponding trifluoromethyl analogues. A phenylsulfur pentafluoride analogue of the insecticide fipronil, screened against a resistant strain of Musca domestica, showed higher activity than the corresponding trifluoromethyl analogue.
- Crowley, Patrick J.,Mitchell, Glynn,Salmon, Roger,Worthington, Paul A.
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p. 138 - 142
(2007/10/03)
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- A new method for the synthesis of aromatic sulfurpentafluorides and studies of the stability of the sulfurpentafluoride group in common synthetic transformations
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A new synthesis of aromatic sulfurpentafluoride compounds is described. Subsequent elaboration of the aromatic rings in the presence of the sulfurpentafluoride group is also discussed for a variety of common synthetic methods. This paper also describes ab initio electronic structure calculations of 3- and 4-aminophenylsulfurpentafluoride, compared with 3- and 4-aminobenzotrifluoride, and presents X-ray crystal structures of two aromatic sulfurpentafluoride derivatives. (C) 2000 Elsevier Science Ltd.
- Bowden, Roy D.,Comina, Paul J.,Greenhall, Martin P.,Kariuki, Benson M.,Loveday, Amanda,Philp, Douglas
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p. 3399 - 3408
(2007/10/03)
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