77570-15-1Relevant articles and documents
SULFONYLUREAS AND RELATED COMPOUNDS AND USE OF SAME
-
Page/Page column 126, (2016/09/15)
ABSTRACT The present invention provides for certain sulfonyl ureas and related compounds which have advantageous properties and show useful activity in the inhibition of activation of the NLRP3 inflammasome. Such compounds are useful in the treatment of a wide range of disorders in which the inflammation process, or more specifically the NLRP3 inflammasome, have been implicated as being a key factor.
Bicyclic imidazolium-based ionic liquids: synthesis and characterization
Kan, Huang-Chuan,Tseng, Ming-Chung,Chu, Yen-Ho
, p. 1644 - 1653 (2007/10/03)
We previously reported the use of imidazole as starting compound for preparing a bicyclic imidazolium ionic liquid, [b-3C-im][NTf2], with an overall 29% isolated yield in four synthetic steps. This new room temperature ionic liquid was shown to be far more chemically stable than commonly used [bmim][PF6], [bdmim][PF6], and [bdmim][NTf2]. Because of this intriguing chemical stability, it prompted us to develop a more generalized and high yielding synthesis so that molecular diversity of bicyclic ionic liquids may be explored. In this work, we amended the previous synthetic route by employing 4-chlorobutyronitrile or 5-chlorovaleronitrile as starting materials and successfully developed a five-step synthesis of a series of novel bicyclic imidazolium-based ionic liquids in 40-53% overall isolated yields. We investigated intrinsic reactivity of all bicyclic ionic liquids prepared and found that, under strongly basic conditions, among all tested ionic liquids the 5,5-membered [R-3C-im][NTf2] ionic liquids were most stable to solvent deuterium isotope exchange while the previously reported [bdmim][NTf2] ionic liquid was 50% deuterium exchanged at its C-2 methyl in 30 min at ambient temperature. Under identical condition, the commonly used [bmim][NTf2] ionic liquid was deuterium exchanged instantaneously at its C-2 hydrogen. In the absence of bases, only [bmim][PF6] was deuterium exchanged (50% within 1 h) and all other ionic liquids gave no detectable exchanges even after 25 days at ambient temperature. Moreover, both [bmim][NTf2] and [bdmim][NTf2] ionic liquids were readily methylated at C-2 position with methyl iodide under basic condition at room temperature. Under the same condition, [R-3C-im][NTf2] and [R-4C-im][NTf2] ionic liquids were completely stable and chemically inert. We envisioned that [R-3C-im][NTf2] should be well suited as solvents for organic synthesis.
