- Copper-catalysed bromoamination of maleimides using NBS as the bromine source
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CuBr2-catalysed bromoamination of maleimides has been achieved in THF with alkylamines and N-bromosuccinimide as nitrogen and bromine sources respectively. The reaction conditions were optimised. A series of bromoamination products such as 3-am
- Kong, De-Huan,An, Yu-Long,Shao, Zhi-Yu,Zhao, Sheng-Yin
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p. 476 - 480
(2018/10/15)
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- Iodine-Promoted C(sp 2)-H thiolation of maleimides with dimethyl sulfoxide and thiols
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Iodine-promoted C(sp 2)-H methylthiolation of maleimides using DMSO as synthon has been developed to afford 3-methylthiomaleimides in moderate yields under metal-free conditions. In addition, 3-thiomaleimides were synthesized from maleimides an
- Tan, Hong-Ru,Wang, Lun,Yang, Zhen-Hua,Zhao, Sheng-Yin,Zhu, Jia-Nan
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p. 4113 - 4123
(2018/10/15)
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- A para-C–H Functionalization of Aniline Derivatives via In situ Generated Bulky Hypervalent Iodinium Reagents
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A practical para-C-H functionalization of aniline derivatives has been developed using an in situ generated bulky hypervalent iodinium reagent. Para-iodo, bromo, chloro, nitro, trifluormethyl aniline derivatives can be obtained efficiently, in many cases in 10 min in a transition metal-free manner. Medicinal chemicals or intermediates can be purified without column chromatography or recrystallization, which significantly reduces the waste and simplifies the work-up process.
- Tian, Chao,Yao, Xu,Ji, Weizhe,Wang, Qian,An, Guanghui,Li, Guangming
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supporting information
p. 5972 - 5979
(2018/11/23)
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- Stable and Rapid Thiol Bioconjugation by Light-Triggered Thiomaleimide Ring Hydrolysis
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Maleimide-mediated thiol-specific derivatization of biomolecules is one of the most efficacious bioconjugation approaches currently available. Alarmingly, however, recent work demonstrates that the resulting thiomaleimide conjugates are susceptible to breakdown via thiol exchange reactions. Herein, we report a new class of maleimides, namely o-CH2NHiPr phenyl maleimides, that undergo unprecedentedly rapid ring hydrolysis after thiol conjugation to form stable thiol exchange-resistant conjugates. Furthermore, we overcome the problem of low shelf lives of maleimide reagents owing to their propensity to undergo ring hydrolysis prior to bioconjugation by developing a photocaged version of this scaffold that resists ring hydrolysis. UV irradiation of thiol bioconjugates formed with this photocaged maleimide unleashes rapid thiomaleimide ring hydrolysis to yield the desired stable conjugates within 1 h under gentle, ice-cold conditions.
- Kalia, Dimpy,Pawar, Sharad P.,Thopate, Jyoti S.
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p. 1885 - 1889
(2017/02/05)
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- Coumarin-based fluorogenic agents and uses thereof for specific protein labelling
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There are provided fluorescent labelling agents comprising a dimaleimide core connected to a fluorophore, processes for preparation thereof, and uses thereof for labelling and/or detection of specific protein targets. Fluorescent labelling agents comprising a compound having the structure of Formula I, and salts thereof, are described.
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- Reversible covalent linkage of functional molecules
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The present invention relates to the use of a compound containing a moiety of formula (I) as a reagent for linking a compound of formula R1—H which comprises a first functional moiety of formula F1 to a second functional moiety of fo
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Page/Page column 57
(2016/04/26)
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- A mild and selective protecting and reversed modification of thiols
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One selective thiol-protecting study has been investigated for a wide range of thiols including general thiols and thiols containing multiple functional groups. The reactions of bromomaleimides and thiols under the mild condition afforded the protected products in excellent yields. The thiols can be recovered very quickly using dithiothreitol (DTT) under the mild condition.
- Li, Xiangmin,Li, Hongxian,Yang, Wei,Zhuang, Jinchen,Li, Hao,Wang, Wei
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p. 2660 - 2663
(2016/06/01)
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- Ring Substituent Effects on the Thiol Addition and Hydrolysis Reactions of N-Arylmaleimides
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Maleimide groups are used extensively in bioconjugation reactions, but limited kinetic information is available regarding their thiol addition and hydrolysis reactions. We prepared a series of fluorogenic coumarin maleimide derivatives that differ by the
- Chen, Yingche,Tsao, Kelvin,De Francesco, élise,Keillor, Jeffrey W.
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p. 12182 - 12192
(2016/01/09)
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- Aryloxymaleimides for cysteine modification, disulfide bridging and the dual functionalization of disulfide bonds
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Tuning the properties of maleimide reagents holds significant promise in expanding the toolbox of available methods for bioconjugation. Herein we describe aryloxymaleimides which represent 'next generation maleimides' of attenuated reactivity, and demonstrate their ability to enable new methods for protein modification at disulfide bonds.
- Marculescu, Cristina,Kossen, Hanno,Morgan, Rachel E.,Mayer, Patrick,Fletcher, Sally A.,Tolner, Berend,Chester, Kerry A.,Jones, Lyn H.,Baker, James R.
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p. 7139 - 7142
(2014/07/07)
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- A tandem [3+2] cycloaddition-elimination cascade reaction to generate pyrrolo-[3,4-c]pyrrole-1,3-diones
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An efficient tandem [3+2] cycloaddition-elimination cascade sequence has been developed enabling assembly of the pharmacologically relevant pyrrolo-[3,4-c]pyrrole-1,3-dione chemotype. The strategy involves simple mixing of readily accessible oxazolin-2-on
- Martinez-Ariza, Guillermo,Dietrich, Justin,De Moliner, Fabio,Hulme, Christopher
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p. 1801 - 1804
(2013/09/12)
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- A Pd[0]-catalyzed Ullmann cross-coupling/reductive cyclization approach to C-3 mono-alkylated oxindoles and related compounds
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The Pd[0]-catalyzed Ullmann cross-coupling of o-nitrohaloarenes 1a-e with the brominated heterocycles 2a-f delivers the expected products 3a-j in good to excellent yields. The reductive cyclization of such products, as well as N-acyl derivatives 3k, l, and m, has been investigated and provided the C-3 mono-substituted oxindoles 5a-d, f, g, k, and m, the direct reduction products 4i and j or indole 5l.
- Banwell, Martin G.,Jones, Matthew T.,Loong, David T.J.,Lupton, David W.,Pinkerton, David M.,Ray, Jayanta K.,Willis, Anthony C.
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experimental part
p. 9252 - 9262
(2011/01/12)
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- Facile routes to alkoxymaleimides/maleic anhydrides
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New routes to alkoxymaleic anhydrides 1a/b have been described in good yields via base-induced chemoselective vinylic substitution of bromo atom in bromomaleimide 4 with alkanols, and base-induced oxa-Micahel addition of alkanols to dialkyl acetylene-dicarboxylates 8a/b as key steps. An unusual acyl exchange in the conversion of 6a/b to 1a/b under very simple and mild reaction conditions is noteworthy.
- Sahoo, Manoj Kumar,Mhaske, Santosh B.,Argade, Narshinha P.
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p. 346 - 349
(2007/10/03)
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- Revised Structures of N-Substituted Dibrominated Pyrrole Derivatives and Their Polymeric Products. Termaleimide Models with Low Optical Band Gaps
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This paper describes an unexpected rearrangement/oxidation of N-substituted 2,5-dibromopyrroles upon treatment with HNO3. The bromides migrate from the 2,5-positions to the 3,4-positions with subsequent oxidation at the 2,5-positions to afford N-substituted 3,4-dibromomaleimides; the structure was confirmed by single-crystal X-ray analysis. The maleimides were then polymerized to the poly(N-substituted-3,4-maleimide)s with copper bronze. This constitutes a revision of structure for the monomers and polymers. The propensity for the dibromide migration was further confirmed by treatment of N-benzyl-2,5-dibromopyrrole under nonoxidative acidic conditions (p-TsOH) to afford N-benzyl-3,4-dibromopyrrole; both the starting material and product structures were confirmed by single-crystal X-ray analysis. Several termaleimides were prepared from pyrrole, maleic anhydride, and citraconic anhydride. These trimeric compounds underwent enormous shifts in their optical absorbance maxima (ca. 200 nm) when bases or nucleophilic solvents were added. Therefore, the termaleimides served as excellent models for the polymeric systems that had undergone shifts of 350-400 nm upon treatment with the same additives. Ab initio Hartree-Fock and density functional theory were utilized to assess the minimum conformation of the trimeric system. Both terminal maleimides appear canted 37° relative to the central maleimide unit. As the two end maleimide units were computationally forced into closer proximity, there was a dipolar stabilization that ensued between the two terminal maleimides with the formation of a 1,3-dioxetane. However, it is unlikely that there could be the formation of an isolable 1,3-dioxetane due to the large energy difference between the canted structure and the dioxetane. A significant decrease in the HOMO-LUMO energy of 13 kcal/mol was calculated upon formation of the 1,3-dioxetane, suggesting that nucleophiles likely move the canted structure more toward a planar form via addition to the α,β-unsaturated carbonyl units.
- Choi, Dong-Sook,Huang, Shenlin,Huang, Mingsheng,Barnard, Thomas S.,Adams, Richard D.,Seminario, Jorge M.,Tour, James M.
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p. 2646 - 2655
(2007/10/03)
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