29431-37-6Relevant articles and documents
Multigram scale synthesis of 3,4- and 3,6-dihydro-2H-thiopyran 1,1-dioxides and features of their NMR spectral behavior
Chabanenko, Roman M.,Yu. Mykolenko, Svitlana,Kozirev, Eugene K.,Palchykov, Vitalii A.
supporting information, p. 2198 - 2205 (2018/07/15)
A new four-step synthesis of 3,4- and 3,6-dihydro-2H-thiopran-1,1-dioxides from dihydro-2H-thiopyran-3(4H)-one is reported. The title compounds are synthesized starting with oxidation of the ketone with a 30% aqueous solution of hydrogen peroxide in a mixture of AcOH-Ac2O. The keto group is then reduced by sodium borohydride followed by mesylation and elimination of methanesulfonic acid under basic conditions (pyridine for 3,4-isomer and aqueous NaOH for 3,6-isomer). This sequence is simpler, than previously known methods, uses cheaper and more readily available reagents, and leads to 2H-thiopran-1,1-dioxides on multigram scale with 64% and 74% total yields, respectively. The structure and purity of the compounds were confirmed by 2D NMR and GCMS methods. The proposed method expands the means to access functionalized cyclic sulfones as building blocks in the synthesis of combinatorial libraries of new biologically active compounds.
Lead optimisation of selective non-zinc binding inhibitors of MMP13. Part 2
De Savi, Chris,Morley, Andrew D.,Nash, Ian,Karoutchi, Galith,Page, Ken,Ting, Attilla,Gerhardt, Stefan
supporting information; experimental part, p. 271 - 277 (2012/02/16)
Directed screening has identified a novel series of non-zinc binding MMP13 inhibitors that possess good levels of activity whilst demonstrating excellent selectivity over related MMPs. A lead optimisation campaign has delivered compounds with enhanced MMP
Synthesis of Novel Cyclic Sulfone Dihydropyridines Facilitated by a Selective Ethyl Diazoacetate Ring Expansion
Dodd, John H.,Schwender, Charles F.,Gray-Nunez, Yolanda
, p. 1453 - 1456 (2007/10/02)
A series of novel cyclic sulfone dihydropyridines with five to nine membered rings have been synthesized.Anomalous intermediates isolated from the Hantzch condensation were found to vary depending on the sulfone ring size and aromatic substitution.Tin tetrachloride has been shown to be a superior Lewis acid catalyst for ethyl diazoacetate ring expansion of the requisite β-keto cyclic sulfone precursors.
