18368-58-6Relevant articles and documents
Base-Activated Latent Heteroaromatic Sulfinates as Nucleophilic Coupling Partners in Palladium-Catalyzed Cross-Coupling Reactions
Cook, Xinlan A. F.,Pantaine, Lo?c R. E.,Blakemore, David C.,Moses, Ian B.,Sach, Neal W.,Shavnya, Andre,Willis, Michael C.
supporting information, p. 22461 - 22468 (2021/09/09)
Heteroaromatic sulfinates are effective nucleophilic reagents in Pd0-catalyzed cross-coupling reactions with aryl halides. However, metal sulfinate salts can be challenging to purify, solubilize in reaction media, and are not tolerant to multi-step transformations. Here we introduce base-activated, latent sulfinate reagents: β-nitrile and β-ester sulfones. We show that under the cross-coupling conditions, these species generate the sulfinate salt in situ, which then undergo efficient palladium-catalyzed desulfinative cross-coupling with (hetero)aryl bromides to deliver a broad range of biaryls. These latent sulfinate reagents have proven to be stable through multi-step substrate elaboration, and amenable to scale-up.
Grignard-Reagent-Promoted Desulfonylation/Intramolecular Coupling for the Synthesis of 2-(1-Fluorovinyl)pyridines
Jiang, Gaoxi,Kang, Lei,Qian, Jinlong,Yang, Huameng,Zhang, Jinlong
supporting information, p. 9118 - 9122 (2020/12/02)
A novel process involving Grignard-reagent-promoted desulfonylation/intramolecular coupling of readily available α-fluoro-α,β-unsaturated-(2-pyridyl)sulfones was realized that provided a series of polysubstituted 2-(1-fluorovinyl)pyridines in good yields. The intrinsic coordination between pyridine and Mg(II) along with the "negative fluorine effect"of the substrates should play the key role for the smooth transformation in the absence of transition-metal catalysts.
Synthesis and characterization of 2-pyridylsulfur pentafluorides
Kanishchev, Oleksandr S.,Dolbier, William R.
supporting information, p. 280 - 284 (2015/04/21)
Current approaches to prepare SF5-substituted heterocycles during the synthesis of targeted heterocyclic compounds require the use of SF5-functionalized aryl or alkyne reagents or SF5Cl as a source of the SF5 functional group. Herein we report that excess oxidative fluorination of 2,2' -dipyridyl disulfide with a KF/Cl2 /MeCN system leads to the formation of thirteen new 2-pyridylsulfur chlorotetrafluorides (2-SF4Cl-pyridines). These molecules are found to undergo further chlorine-fluorine exchange reactions by treatment with silver(I) fluoride enabling ready access to a series of ten new substituted 2-pyridylsulfur pentafluorides (2-SF5-pyridines). This is the first preparatively simple and readily scalable example of the transformation of an existing heterocyclic sulfur functionality to prepare SF5-substituted heterocycles.
COMPOUNDS FOR MODULATING TRPV3 FUNCTION
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Page/Page column 103, (2010/11/30)
The present application relates to compounds and methods for treating pain and other conditions related to TRP V3.
SULPHONAMIDES
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, (2008/06/13)
Compounds of the formula STR1 wherein the variables are hereinbelow defined. The compounds of formula I are inhibitors for endothelin receptors. They can be used for the treatment of disorders which are associated with endothelin activities, especially circulatory disorders such as hypertension, ischaemia, vasospasms and angina pectoris.
Discovery of Ro 48-5695: A potent mixed endothelin receptor antagonist optimized from Bosentan
Neidhart, Werner,Breu, Volker,Burri, Kaspar,Clozel, Martine,Hirth, Georges,Klinkhammer, Uwe,Giller, Thomas,Ramuz, Henri
, p. 2223 - 2228 (2007/10/03)
Implementation of a pyridylcarbamoyl group and an isopropylpyridylsulfonamide substituent as key components in the scaffold of Bosentan resulted in the identification of the potent orally active endothelin receptor antagonist Ro 48-5695. It shows affinities for ET(A) and ET(B) receptors in the low nanomolar range and high functional antagonistic potency in vitro.
Azetidinone compounds useful in the preparation of carbapenem antibiotics and process for preparing carbapenem and penem compounds
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, (2008/06/13)
Compounds of formula (I): STR1 wherein: R1 is hydrogen or a hydroxy-protecting group; R2 is alkyl, alkoxy, halogen, optionally substituted phenyl or optionally substituted phenoxy; R3 is optionally substituted pyridyl, optionally substituted quinolyl or phenyl group which has a substituent of formula --CYNR5 R6, where Y is oxygen or sulfur, and R5 and R6 are each alkyl, aryl or aralkyl, or R5 and R6 and the nitrogen to which they are attached together form a heterocyclic group; is R4 hydrogen or an amino-protecting group; and Z is sulfur or oxygen; are valuable intermediates in the preparation of carbapenem compounds and retain a desirable configuration during conversion to such carbapenem compounds. Penem and carbapenem compounds having a group of formula --SA' are prepared from a corresponding compound having a substituted thio, sulfinyl or sulfonyl group at this position by reaction with a compound A'SH (where A' is an organic group) in the presence of a salt of a metal of Group II or III of the Periodic Table.
The Synthesis and Some Reactions of Novel Pyridine-2(1H)-thiones
Dunn, A. D.,Norrie, R.,L'Hostis, J.,Marjot, S.
, p. 119 - 125 (2007/10/02)
The use of methyl 3-mercaptopropionate for the conversion of halogenated pyridins to pyridine thiones and thiols is described, and limitations of the reaction discussed.S-Alkylation and oxidation reactions of the products from these reactions are reported.
