182323-20-2Relevant academic research and scientific papers
The reaction of [N-(p-toluenesulfonyl)imino]phenyliodinane with enol silanes
Lim, Byeong-Woo,Ahn, Kwang-Hyun
, p. 3407 - 3412 (1996)
[N-(p-Toluenesulfonyl)imino]phenyliodinane reacts with enol silanes to provide α-tosylamino carbonyl compounds.
Highly Selective Oxidative Cleavage of β-Cyclodextrin - Epoxide/Aziridine Complexes with IBX in Water
Surendra,Krishnaveni, N. Srilakshmi,Reddy, M. Arjun,Nageswar,Rao, K. Rama
, p. 9119 - 9121 (2003)
Water, an environmentally friendly reaction medium, has been utilized for the reaction of IBX with various epoxides 1 and aziridines 2 as their β-cyclodextrin complexes to afford for the first time α -hydroxyketones 3 and α-aminoketones 4, respectively.
The reaction of prop-2-ynylsulfonium salts and sulfonyl-protected β-amino ketones to epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles
Jia, Tingting,Zeng, Gongruixue,Zhang, Chong,Zeng, Linghui,Zheng, Wenya,Li, Siyao,Wu, Keyi,Shao, Jiaan,Zhang, Jiankang,Zhu, Huajian
, p. 2657 - 2660 (2021/03/16)
A novel divergent domino annulation reaction of prop-2-ynylsulfonium salts with sulfonyl-protected β-amino ketones has been developed, affording various epoxide-fused 2-methylenepyrrolidines and S-containing pyrroles in moderate to excellent yields. Prop-2-ynylsulfonium salts act as C2synthons in the reactions providing a promising epoxide-fused skeleton in a single operation with readily accessible starting materials.
Photoactivated N-Acyliminoiodinanes Applied to Amination: an ortho-Methoxymethyl Group Stabilizes Reactive Precursors
Kobayashi, Yusuke,Masakado, Sota,Takemoto, Yoshiji
supporting information, p. 693 - 697 (2018/01/17)
N-Acyliminoiodinanes were characterized for the first time by X-ray structural analysis. The ortho-methoxymethyl group and the carbonyl oxygen coordinate to the iodine atom of the iminoiodinane. Activation of the N-acyliminoiodinane was achieved by photoirradiation at 370 nm, thereby enabling reaction with various silyl enol ethers to give α-aminoketone derivatives in good to high yield. N-sulfonyliminoiodinanes bearing ortho substituents were used in photoinduced amination.
Flexible stereoselective functionalizations of ketones through umpolung with hypervalent iodine reagents
Mizar, Pushpak,Wirth, Thomas
, p. 5993 - 5997 (2014/06/10)
The functionalization of carbonyl compounds in the α-position has gathered much attention as a synthetic route because of the wide biological importance of such products. Through polarity reversal, or "umpolung", we show here that typical nucleophiles, such as oxygen, nitrogen, and even carbon nucleophiles, can be used for addition reactions after tethering them to enol ethers. Our findings allow novel retrosynthetic planning and rapid assembly of structures previously accessible only by multistep sequences. A Nu approach: An efficient α-functionalization of ketones with a range of simple and useful nucleophiles is possible by using hypervalent iodine reagents (see scheme; Nu′ can be the Nu itself or a protected form of this nucleophile group).
Synthesis of α-amino ketones from terminal alkynes via rhodium-catalyzed denitrogenative hydration of N -sulfonyl-1,2,3-triazoles
Miura, Tomoya,Biyajima, Tsuneaki,Fujii, Tetsuji,Murakami, Masahiro
supporting information; experimental part, p. 194 - 196 (2012/03/07)
N-Sulfonyl-1,2,3-triazoles react with water in the presence of a rhodium catalyst to produce α-amino ketones in high yield. An intermediary α-imino rhodium(II) carbenoid undergoes insertion into the O-H bond of water. This transformation formally achieves 1,2-aminohydroxylation of terminal alkynes in a regioselective fashion when combined with the copper(I)-catalyzed 1,3-dipolar cycloaddition with N-sulfonyl azides.
O-alkoxyphenyliminoiodanes: Highly efficient reagents for the catalytic aziridination of alkenes and the metal-free amination of organic substrates
Yoshimura, Akira,Nemykin, Victor N.,Zhdankin, Viktor V.
supporting information; experimental part, p. 10538 - 10541 (2011/11/12)
Efficient nitrene precursors: Highly reactive iminoiodane-based nitrene precursors were prepared from ortho-alkoxyiodobenzenes. Owing to the presence of the ortho-substituent on the phenyl ring, these new iminoiodanes have excellent solubility in organic
Novel three-component synthesis and antiproliferative properties of diversely functionalized pyrrolines
Magedov, Igor V.,Luchetti, Giovanni,Evdokimov, Nikolai M.,Manpadi, Madhuri,Steelant, Wim F.A.,Van slambrouck, Severine,Tongwa, Paul,Antipin, Mikhail Yu.,Kornienko, Alexander
, p. 1392 - 1396 (2008/12/23)
Diversely substituted 2-pyrrolines have been prepared by a novel multicomponent process involving a reaction of various N-(aryl- and alkylsulfonamido)-acetophenones with aldehydes and malononitrile. While the reaction is highly regioselective, it is not s
Pyrrolotriazine-5-carboxylate ester inhibitors of EGFR and HER2 protein tyrosine kinases and a novel one-pot synthesis of C-4 subsitituted pyrrole-2,3-dicarboxylate diesters
Mastalerz, Harold,Gavai, Ashvinikumar V.,Fink, Brian,Struzynski, Charles,Tarrant, James,Vite, Gregory D.,Wong, Tai W.,Zhang, Guifen,Vyas, Dolatrai M.
, p. 528 - 533 (2007/10/03)
Pyrrolotriazines with an ester group at C-5 were prepared and evaluated as inhibitors of the EGFR and HER2 receptor tyrosine kinases, validated targets for cancer therapy. The C-5 ester (15) was at least as potent as its C-6 ester analogue (17), an exampl
A mild and efficient procedure for the oxidation of epoxides and aziridines using cerium(IV) ammonium nitrate and NBS
Surendra,Srilakshmi Krishnaveni,Rama Rao
, p. 4111 - 4113 (2007/10/03)
The CAN and NBS combination has been used for the first time for the synthesis of versatile α-hydroxy ketones and α-amino ketones from oxiranes/aziridines, respectively, in excellent yields. This method is a direct, one-pot, synthesis under mild conditions using acetonitrile-water (9:1) as solvent.
