2849-81-2Relevant academic research and scientific papers
A novel synthesis of 3-aminoazetidines by ring transformation of 2-(bromomethyl)aziridines
Karikomi, Michinori,De Kimpe, Norbert
, p. 10295 - 10298 (2000)
A one-step approach to the biologically interesting 3-aminoazetidines is described. The reaction concerns a ring transformation of 1-arylsulfonyl-2-(halomethyl)aziridines with aliphatic amines under various reaction conditions. (C) 2000 Elsevier Science Ltd.
Access to 1-Phospha-2-azanorbornenes by Phospha-aza-Diels–Alder Reactions
Wonneberger, Peter,K?nig, Nils,Kraft, Fabian B.,Sárosi, Menyhárt B.,Hey-Hawkins, Evamarie
, p. 3208 - 3211 (2019)
The unprecedented phospha-aza-Diels–Alder reaction between an activated electron-poor imine and 2H-phospholes yields 1-phospha-2-azanorbornenes in a highly chemoselective and moderately diastereoselective reaction. The intermediate 2H-phospholes, which ac
Development of an Imine Chaperone for Selective C-H Functionalization of Alcohols via Radical Relay
Nakafuku, Kohki M.,Twumasi, Raymond K.,Vanitcha, Avassaya,Wappes, Ethan A.,Namitharan, Kayambu,Bekkaye, Mathieu,Nagib, David A.
, p. 13065 - 13072 (2019)
The design of a radical relay chaperone to promote selective C-H functionalizations is described. A saccharin-based imine was found to be uniquely suited to effect C-H amination of alcohols via an in situ generated hemiaminal. This radical chaperone facilitates the mild generation of an N-centered radical while also directing its regioselective H atom transfer (HAT) to the β carbon of an alcohol. Upon β C-H halogenation, aminocyclization, and reductive cleavage, an NH2 is formally added vicinal to an alcohol. The development, synthetic utility, and chemo-, regio-, and stereoselectivity of this imine chaperone-mediated C-H amination is presented herein.
Copper-Catalyzed Intermolecular Alkynylation and Allylation of Unactivated C(sp3)-H Bonds via Hydrogen Atom Transfer
Liang, Lei,Guo, Ge,Li, Chen,Wang, Song-Lin,Wang, Yue-Hui,Guo, Hai-Ming,Niu, Hong-Ying
supporting information, p. 8575 - 8579 (2021/11/13)
We describe Cu-catalyzed intermolecular alkynylation and allylation of unactivated C(sp3)-H bonds with singly occupied molecular orbital-philes (SOMO-philes) via hydrogen atom transfer (HAT). Employing N-fluoro-sulfonamide as a HAT reagent, a set of subst
Recurrent Approximation of Retention Parameters of N-Substituted p-Toluenesulfonamides in Reversed-Phase High Performance Liquid Chromatography for Revealing the Formation of Their Hydrates
Kornilova, T. A.,Nikitina, D. A.,Zenkevich, I. G.
, p. 1931 - 1941 (2021/09/15)
Abstract: Recurrent approximation of retention times in reversed-phase high performance liquid chromatography (RP-HPLC), tR(C + ΔC) = atR(C) + b, where C is the acetonitrile concentration in the eluent, and ΔC is the constant “step” of its variation, for six specially synthesized N-substituted p-toluenesulfonamides confirmed the presence of anomalies previously revealed for some complex polyfunctional organic compounds. The reason for these anomalies is the presence of sulfonamide –SO2–NH fragments in the molecules, which leads to hydration of sorbates in aqueous solutions, or, more precisely, to a change in the ratio of their non-hydrated and hydrated forms because of a shift in the equilibrium Х + Н2О $$ rightleftarrows $$ Х·Н2О (*) as a result of a change in the eluent composition. The same effect is indicated by the strong antibatic dependence of the retention indices RI(C) of all sulfonamides under study; the coefficients dRI/dC vary from –1.9 to –4.0, these values being much higher in magnitude than for compounds that do not form hydrates. Further independent evidence in favor of the transformation of sorbates due to variation of the eluent composition is the dependence of the relative absorbance Arel = A(254)/A(220) on the acetonitrile content in the eluent. This suggests changes in the chemical nature of chromophores in sulfonamide molecules depending on the equilibrium state (*).
Organophotoredox-Catalyzed Decarboxylative N-Alkylation of Sulfonamides
Nakagawa, Masanari,Nagao, Kazunori,Ikeda, Zenichi,Reynolds, Matthew,Ibá?ez, Ignacio,Wang, Junsi,Tokunaga, Norihito,Sasaki, Yusuke,Ohmiya, Hirohisa
, p. 3930 - 3933 (2021/08/03)
We developed an organophotoredox-catalyzed reaction for N-alkylation of sulfonamides with aliphatic carboxylic acid-derived redox active esters as alkylating reagents. Under mild and transition metal-free conditions, a series of functionalized N-alkylated sulfonamides were prepared. This protocol also enabled the functionalization of pharmaceutical drugs bearing a sulfonamide or carboxylic acid moiety. This radical-mediated process allowed the assembly of three components including sulfonamides, redox active esters, and alkenes to yield complex sulfonamides in a one-pot manner.
Zn- And Cu-catalyzed coupling of tertiary alkyl bromides and oxalates to forge challenging C?O, C?S, and C?N bonds
Gong, Yuxin,Zhu, Zhaodong,Qian, Qun,Tong, Weiqi,Gong, Hegui
supporting information, p. 1005 - 1010 (2021/02/01)
We describe here the facile construction of sterically hindered tertiary alkyl ethers and thioethers via the Zn(OTf)2catalyzed coupling of alcohols/phenols with unactivated tertiary alkyl bromides and the Cu(OTf)2-catalyzed thiolation of unactivated tertiary alkyl oxalates with thiols. The present protocol represents one of the most effective unactivated tertiary C(sp3)? heteroatom bond-forming conditions via readily accessible Lewis acid catalysis that is surprisingly less developed.
Facile synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazides
Chen, Rongxiang,Xu, Shaohong,Shen, Fumin,Xu, Canran,Wang, Kaikai,Wang, Zhanyong,Liu, Lantao
, (2021/09/20)
A simple and rapid method for efficient synthesis of sulfonyl chlorides/bromides from sulfonyl hydrazide with NXS (X = Cl or Br) and late-stage conversion to several other functional groups was described. A variety of nucleophiles could be engaged in this transformation, thus permitting the synthesis of complex sulfonamides and sulfonates. In most cases, these reactions are highly selective, simple, and clean, affording products at excellent yields.
COMPOUNDS AND COMPOSITIONS FOR TREATING CONDITIONS ASSOCIATED WITH NLRP ACTIVITY
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Page/Page column 253-254, (2020/06/05)
In one aspect, compounds of Formula AA, or a pharmaceutically acceptable salt thereof, are featured or a pharmaceutically acceptable salt thereof, wherein the variables shown in Formula A can be as defined anywhere herein.
Synthesis of chiral a-substituted a-amino acid and amine derivatives through Ni-catalyzed asymmetric hydrogenation
Cong, Hengjiang,Dong, Xiu-Qin,Liu, Gongyi,Wang, Heng,Zhang, Xianghe,Zhang, Xumu
supporting information, p. 4934 - 4937 (2020/05/13)
Highly efficient Ni-catalyzed asymmetric hydrogenation of cyclicN-sulfonyl ketimino esters was, for the first time, successfully developed, providing various chiral a-monosubstituted a-amino acid derivatives with excellent results (97-99% yields, 90 to >99% ee). CyclicN-sulfonyl ketimines were also hydrogenated well to afford chiral amine derivatives with 98-99% yields and 97 to >99% ee. The gram-scale asymmetric hydrogenation was performed well with 85% yield and 99% ee using only 0.2 mol% catalyst.
