- Crossover inhibition as an indicator of convergent evolution of enzyme mechanisms: A β-lactamase and a N-terminal nucleophile hydrolase
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O-Aryloxycarbonyl hydroxamates and 1,3,4-oxathiazol-2-ones have been identified as covalent inhibitors of β-lactamases and proteasomes, respectively. The products of these inhibition reactions are remarkably similar, involving carbonyl cross-linking of the active sites. We have cross-checked these inhibitors, showing that the former inhibit proteasomes and the latter β-lactamases, to form the same inactive carbonyl adducts. These results are discussed in terms of similarities of the active site structures and catalytic mechanisms. It is likely that a mechanistic imperative has led to convergent evolution of these enzyme active sites, of a β-lactam-recognizing enzyme and a N-terminal protease belonging to different amidohydrolase superfamilies.
- Adediran,Lin,Pelto,Pratt
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Read Online
- Rhodium(III)-Catalyzed Aldehyde C?H Activation and Functionalization with Dioxazolones: An Entry to Imide Synthesis
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A rhodium(III)-based catalytic system has been used to develop a C?H bond activation of benzaldehyde derivatives and subsequent functionalization with dioxazolones in order to afford imides. The importance of the nature of the directing group to perform selectively the aldehydic C?H bond activation has been highlighted. The scope investigation showed that this transformation could be applied to various dioxazolones and many benzaldehyde derivatives as well as an acrolein derivative. Derivatization reactions of the imide products demonstrated the synthetic utility of this rhodium-catalyzed aldehydic C?H amidation.
- Massouh, Joe,Petrelli, Antoine,Bellière-Baca, Virginie,Hérault, Damien,Clavier, Hervé
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p. 831 - 837
(2022/01/06)
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- Cu(II)-Catalyzed C-H Amidation/Cyclization of Azomethine Imines with Dioxazolones via Acyl Nitrenes: A Direct Access to Diverse 1,2,4-Triazole Derivatives
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We report a Cu(II)-catalyzed C-H amidation/cyclization of azomethine imines with dioxazolones as acyl nitrene transfer reagents under additive-and ligand-free conditions. An array of 1,2,4-triazolo[1,5-a]pyridine derivatives were afforded in moderate to good yields with excellent functional group tolerance. In addition, scale-up reaction and photoluminescence properties were discussed.
- Liu, Xiang,Li, Wen,Jiang, Wenxuan,Lu, Hao,Liu, Jiali,Lin, Yijun,Cao, Hua
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p. 613 - 618
(2022/01/20)
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- Chemical Upcycling of Waste Poly(bisphenol A carbonate) to 1,4,2-Dioxazol-5-ones and One-Pot C?H Amidation
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Chemical upcycling of poly(bisphenol A carbonate) (PC) was achieved in this study with hydroxamic acid nucleophiles, giving rise to synthetically valuable 1,4,2-dioxazol-5-ones and bisphenol A. Using 1,5,7-triazabicyclo[4.4.0]-dec-5-ene (TBD), non-green carbodiimidazole or phosgene carbonylation agents used in conventional dioxazolone synthesis were successfully replaced with PC, and environmentally harmful bisphenol A was simultaneously recovered. Assorted hydroxamic acids exhibited good-to-excellent efficiencies and green chemical features, promising broad synthetic application scope. In addition, a green aryl amide synthesis process was developed, involving one-pot depolymerization from polycarbonate to dioxazolone followed by rhodium-catalyzed C?H amidation, including gram-scale examples with used compact discs.
- Jung, Hyun Jin,Park, Sora,Lee, Hyun Sub,Shin, Hyun Gyu,Yoo, Yeji,Baral, Ek Raj,Lee, Jun Hee,Kwak, Jaesung,Kim, Jeung Gon
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p. 4301 - 4306
(2021/07/09)
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- Silver-Catalyzed Acyl Nitrene Transfer Reactions Involving Dioxazolones: Direct Assembly of N-Acylureas
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Dioxazolones and isocyanides are useful synthetic building blocks, and have attracted significant attention from researchers. However, the silver-catalyzed nitrene transfer reaction of dioxazolones has not been investigated to date. Herein, a silver-catalyzed acyl nitrene transfer reaction involving dioxazolones, isocyanides, and water was realized in the presence of Ag2O to afford a series of N-acylureas in moderate to good yields.
- Yang, Zheng-Lin,Xu, Xin-Liang,Chen, Xue-Rong,Mao, Zhi-Feng,Zhou, Yi-Feng
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p. 648 - 652
(2020/12/21)
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- Thioether-Directed NiH-Catalyzed Remote γ-C(sp3)-H Hydroamidation of Alkenes by 1,4,2-Dioxazol-5-ones
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A NiH-catalyzed thioether-directed cyclometalation strategy is developed to enable remote methylene C-H bond amidation of unactivated alkenes. Due to the preference for five-membered nickelacycle formation, the chain-walking isomerization initiated by the NiH insertion to an alkene can be terminated at the γ-methylene site remote from the alkene moiety. By employing 2,9-dibutyl-1,10-phenanthroline as the ligand and dioxazolones as the reagent, the amidation occurs at the γ-C(sp3)-H bonds to afford the amide products in up to 90% yield (>40 examples) with remarkable regioselectivity (up to 24:1 rr).
- Chen, Qishu,Du, Bingnan,Ouyang, Yuxin,Yu, Wing-Yiu
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p. 14962 - 14968
(2021/09/29)
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- Direct synthesis of benzoxazinones via Cp*Co(III)-catalyzed C–H activation and annulation of sulfoxonium ylides with dioxazolones
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A highly novel and direct synthesis of benzoxazinones was developed via Cp*Co(III)-catalyzed C–H activation and [3 + 3] annulation between sulfoxonium ylides and dioxazolones. The reaction is conducted under base-free conditions and tolerates various functional groups. Starting from diverse readily available sulfoxonium ylides and dioxazolones, a variety of benzoxazinones could be synthesized in one step in 32%-75% yields.
- Yu, Yongqi,Xia, Zhen,Wu, Qianlong,Liu, Da,Yu, Lin,Xiao, Yuanjiu,Tan, Ze,Deng, Wei,Zhu, Gangguo
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p. 1263 - 1266
(2020/10/08)
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- 1,4,2-Dioxazol-5-ones as Isocyanate Equivalents: An Efficient Synthesis of 2-Quinolinones via β-Keto Amides
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Under thermal conditions, 1,4,2-dioxazol-5-ones are known to undergo decarboxylation followed by Lossen's rearrangement to yield isocyanates. Described herein is the in situ trapping of the resulting isocyanates with carbon nucleophiles to synthesize β-keto amides. Furthermore, a general and mild method for the conversion of the resulting β-keto amides into quinolin-2-ones is reported.
- Vala, Anand,Parmar, Nirali,Soni, Jigar Y.,Kotturi, Sharadsrikar,Guduru, Ramakrishna
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supporting information
p. 2080 - 2084
(2021/10/07)
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- Interweaving Visible-Light and Iron Catalysis for Nitrene Formation and Transformation with Dioxazolones
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Herein, visible-light-driven iron-catalyzed nitrene transfer reactions with dioxazolones for intermolecular C(sp3)-N, N=S, and N=P bond formation are described. These reactions occur with exogenous-ligand-free process and feature satisfactory to excellent yields (up to 99 %), an ample substrate scope (109 examples) under mild reaction conditions. In contrast to intramolecular C?H amidations strategies, an intermolecular regioselective C?H amidation via visible-light-induced nitrene transfer reactions is devised. Mechanistic studies indicate that the reaction proceeds via a radical pathway. Computational studies show that the decarboxylation of dioxazolone depends on the conversion of ground sextet state dioxazolone-bounding iron species to quartet spin state via visible-light irradiation.
- Tang, Jing-Jing,Yu, Xiaoqiang,Wang, Yi,Yamamoto, Yoshinori,Bao, Ming
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supporting information
p. 16426 - 16435
(2021/05/13)
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- Chiral amination sulfoxide and preparation method thereof (by machine translation)
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The invention belongs to the field of organic synthesis, and discloses chiral amination sulfoxide which has the structure of a general formula I. Wherein R is hydrogen or R1 And R2 Each independently selected from one of the following structures: hydrogen, alkyl, alkoxy, ester, trifluoromethyl, trifluoromethoxy, trifluoromethylthio. Halogens, alkynyl groups, alkenyl groups, amino groups, cyano groups, hydroxyl groups, aldehyde groups, carboxyl groups, nitro groups, amide groups, benzene rings, and bonded benzene ring fused rings to naphthalene; R3 Selected from the group consisting of phenyl, optionally substituted phenyl, aryl, heteroaryl, styryl, alkyl, haloalkyl and the like. The method comprises the following steps: forming a complex with a tert-butyl cyclopentadienyl metal iridium complex, forming a complex with the modified chiral proline, and activating C-H bond of enantioselective induced sulfoxide to obtain chiral sulphoxide. The synthetic method disclosed by the invention is high in yield and good in enantioselectivity, and the obtained amidated sulfoxide can be derivatized to obtain a chiral ligand. (by machine translation)
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Paragraph 0245; 0257-0259; 0260-0262
(2020/11/12)
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- Co(III)-Catalyzed C-H Amidation of Nitrogen-Containing Heterocycles with Dioxazolones under Mild Conditions
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A cobalt(III)-catalyzed C-8 selective C-H amidation of quinoline N-oxide using dioxazolone as an amidating reagent under mild conditions is disclosed. The reaction proceeds efficiently with excellent functional group compatibility. The utility of the current method is demonstrated by gram scale synthesis of C-8 amide quinoline N-oxide and by converting this amidated product into functionalized quinolines. Furthermore, the developed catalytic method is also applicable for C-7 amidation of N-pyrimidylindolines and ortho-amidation of benzamides.
- Dhiman, Ankit Kumar,Thakur, Ankita,Kumar, Inder,Kumar, Rakesh,Sharma, Upendra
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p. 9244 - 9254
(2020/08/14)
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- Ortho–C–H amidations enabled by a recyclable manganese-ionic liquid catalytic system
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We described an environmentally benign, recyclable base metal catalyst system (MnBr(CO)5/[Hmim]OAc) for ortho–C–H amidation. The readily available dioxazolones was used as the amidation agents. A broad substrate scope and high functional group
- Kong, Xianqiang,Xu, Bo
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supporting information
(2019/12/27)
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- Ketone-Directed Cobalt(III)-Catalyzed Regioselective C2 Amidation of Indoles
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An efficient cobalt(III)-catalyzed method for the direct C-H amidation of unprotected indoles for 2-amino indole scaffold construction has been developed. With dioxazolone as the amidating reagent, a variety of 2-amino indole derivatives were achieved in moderate to excellent yields using an organic acid as the additive and a ketone as the directing group.
- Shi, Xinxia,Xu, Weiyan,Wang, Rongchao,Zeng, Xiaofei,Qiu, Huayu,Wang, Min
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p. 3911 - 3920
(2020/03/23)
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- Carbamates: A Directing Group for Selective C-H Amidation and Alkylation under Cp*Co(III) Catalysis
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The selective reactivity of carbamate and thiocarbamate toward alkylation and amidation is reported under stable, high-valent, cost-effective cobalt(III) catalysis. This method reveals the wide possibility of designing a different branch of synthetically
- Bera, Sourav Sekhar,Maji, Modhu Sudan
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supporting information
p. 2615 - 2620
(2020/04/08)
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- Phthalazinone-Assisted C-H Amidation Using Dioxazolones under Rh(III) Catalysis
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The preparation of phthalazinone derivatives is pivotal for their utilization as pharmaceutical agents and other entities. Herein, we report the phthalazinone-assisted carbon-nitrogen bond forming reaction using dioxazolones as robust amidation sources under Rh(III) catalysis. The broad functional group tolerance and complete site-selectivity are observed. Notably, a series of transformations of synthesized compounds into biologically relevant N-heterocycles demonstrates the applicability of the developed methodology.
- Jeoung, Daeun,Kim, Kunyoung,Han, Sang Hoon,Ghosh, Prithwish,Lee, Suk Hun,Kim, Saegun,An, Won,Kim, Hyung Sik,Mishra, Neeraj Kumar,Kim, In Su
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p. 7014 - 7023
(2020/07/07)
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- Rhodium(iii)-catalyzed diamidation of olefins: Via amidorhodation and further amidation
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Rh(iii)-catalyzed synthesis of vicinal diamides has been realized via elaboration of an authenticated Rh-C(sp3) species generated via initial intramolecular amidorhodation of olefins. The second amidation was achieved using both electrophilic and nucleophilic amidating reagents. The reactions proceeded under mild conditions with good yield, broad substrate scope, and excellent functional-group tolerance.
- Wang, Jinlei,Zheng, Guangfan,Li, Xingwei
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supporting information
p. 7809 - 7812
(2020/07/27)
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- Cp*Co(III)-catalyzed C[sbnd]H amidation of azines with dioxazolones
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Cp*Co(III)-catalyzed direct C[sbnd]H amidation of azines has been developed. This conversion could proceed smoothly in the absence of external oxidants, acids or bases, with excellent regioselectivity and broad functional group tolerance. CO2 w
- Huang, Yanzhen,Pi, Chao,Tang, Zhen,Wu, Yangjie,Cui, Xiuling
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supporting information
p. 3237 - 3240
(2020/09/15)
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- METHOD FOR THE SYNTHESIS OF 3-R-1,4,2-DIOXAZOL-5-ONES TECHNICAL FIELD
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Provided are methods of preparing 3-R-1,4,2-dioxazol-5-one compounds using convenient and efficient methods. Also provided are 3-R-1,4,2-dioxazol-5-one compounds produced using the methods described.
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Paragraph 0061; 0064-0066; 0068; 0070-0071
(2020/12/25)
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- Efficient Copper-Catalyzed Multicomponent Synthesis of N-Acyl Amidines via Acyl Nitrenes
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Direct synthetic routes to amidines are desired, as they are widely present in many biologically active compounds and organometallic complexes. N-Acyl amidines in particular can be used as a starting material for the synthesis of heterocycles and have several other applications. Here, we describe a fast and practical copper-catalyzed three-component reaction of aryl acetylenes, amines, and easily accessible 1,4,2-dioxazol-5-ones to N-acyl amidines, generating CO2 as the only byproduct. Transformation of the dioxazolones on the Cu catalyst generates acyl nitrenes that rapidly insert into the copper acetylide Cu-C bond rather than undergoing an undesired Curtius rearrangement. For nonaromatic dioxazolones, [Cu(OAc)(Xantphos)] is a superior catalyst for this transformation, leading to full substrate conversion within 10 min. For the direct synthesis of N-benzoyl amidine derivatives from aromatic dioxazolones, [Cu(OAc)(Xantphos)] proved to be inactive, but moderate to good yields were obtained when using simple copper(I) iodide (CuI) as the catalyst. Mechanistic studies revealed the aerobic instability of one of the intermediates at low catalyst loadings, but the reaction could still be performed in air for most substrates when using catalyst loadings of 5 mol %. The herein reported procedure not only provides a new, practical, and direct route to N-acyl amidines but also represents a new type of C-N bond formation.
- Van Vliet, Kaj M.,Polak, Lara H.,Siegler, Maxime A.,Van Der Vlugt, Jarl Ivar,Guerra, Célia Fonseca,De Bruin, Bas
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p. 15240 - 15249
(2019/10/19)
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- Rhodium(iii)-catalyzed cascade reactions of benzoic acids with dioxazolones: Discovery of 2,5-substituted benzoxazinones as AIE molecules
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A rhodium-catalyzed cascade reaction of benzoic acids with 1,4,2-dioxazol-5-ones was studied. The carboxyl group enabled a double C-H amidation followed by further intramolecular cyclization to afford 2,5-substituted benzoxazinones, which exhibited aggregation-induced emission (AIE) properties with a promising excited-state intramolecular proton-transfer (ESIPT) phenomenon.
- Li, Jinbiao,Zhang, Shuaizhong,Lonka, Madhava Reddy,Zhang, Jinquan,Zou, Hongbin
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supporting information
p. 11203 - 11206
(2019/09/30)
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- Ir-Catalyzed Intermolecular Branch-Selective Allylic C-H Amidation of Unactivated Terminal Olefins
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An efficient method for intermolecular branch-selective allylic C-H amidation has been accomplished via Ir(III) catalysis. The reaction proceeds through initial allylic C-H activation, supported by the isolation and crystallographic characterization of an allyl-Ir(III) intermediate, followed by a subsequent oxidative amidation with readily available dioxazolones as nitrenoid precursors. A diverse range of amides are successfully installed at the branched position of terminal alkenes in good yields and regioselectivities. Importantly, the reaction allows the use of amide-derived nitrenoid precursors avoiding problematic Curtius-type rearrangements.
- Lei, Honghui,Rovis, Tomislav
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supporting information
p. 2268 - 2273
(2019/03/05)
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- Synthesis of isoquinolone via rhodium(III)-catalyzed C-H activation with 1,4,2-dioxazol-5-ones as oxidizing directing group
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An efficient rhodium-catalyzed direct C-H activation for the synthesis of isoquinolone with 1,4,2-dioxazol-5-ones as oxidizing directing groups have been developed, which featured mild reaction conditions, short reaction time and satisfactory yield.
- Zhu, Huajian,Zhuang, Rangxiao,Zheng, Wenya,Fu, Liping,Zhao, Yuanke,Tu, Luping,Chai, Yitao,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang
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p. 3108 - 3112
(2019/05/08)
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- Experimental and computational studies on H2O-promoted, Rh-catalyzed transient-ligand-free ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones
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An efficient and convenient ligand-free, rhodium-catalyzed ortho-C(sp2)-H amidation of benzaldehydes with dioxazolones using H2O as the key promoter is described. Using this protocol, a wide range of benzaldehyde substrates were selectively amidated in good to excellent yields with broad functional group compatibility. KIE experiments revealed that the C-H bond activation was likely the rate-limiting step. In addition, computational studies indicated that the catalyst precursor interacted with water and dioxazolones to generate the active catalytic species. Notably, the practicality and efficacy of this method were illustrated by a late-stage amidation of an estrone-derived molecule and further transformations of the amidated product.
- Ding, Jun,Jiang, Wei,Bai, He-Yuan,Ding, Tong-Mei,Gao, Dafang,Bao, Xiaoguang,Zhang, Shu-Yu
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p. 8889 - 8892
(2018/08/17)
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- Rh-Catalyzed Annulation of ortho-C?H Bonds of 2-Arylimidazoles with 1,4,2-Dioxazol-5-ones toward 5-Arylimidazo[1,2-c]quinazolines
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A Rh-catalyzed unique and direct approach for constructing a series of 5-arylimidazo[1,2-c]quinazolines in moderate to excellent yields from simple and readily available 2-arylimidazoles and 3-phenyl-1,4,2-dioxazol-5-ones was described. This procedure pro
- Wu, Xiaopeng,Sun, Song,Xu, Shengbo,Cheng, Jiang
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supporting information
p. 1111 - 1115
(2018/01/27)
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- Tf2NH-Catalyzed Formal [3 + 2] Cycloaddition of Ynamides with Dioxazoles: A Metal-Free Approach to Polysubstituted 4-Aminooxazoles
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An unprecedented Tf2NH-catalyzed formal [3 + 2] cycloaddition of ynamides with dioxazoles was developed to construct various polysubstituted 4-aminooxazoles. This approach features a metal-free catalytic bimolecular assembly of oxazole motifs, a low-cost catalyst, exceptionally mild reaction conditions, a very short reaction time, a broad substrate scope, and high efficiency. This metal-free protocol may find applications in pharmaceutical-oriented synthesis.
- Zhao, Yingying,Hu, Yancheng,Wang, Chunxiang,Li, Xincheng,Wan, Boshun
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p. 3935 - 3942
(2017/04/11)
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- Iterative C?H Functionalization Leading to Multiple Amidations of Anilides
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Polyaminobenzenes were synthesized by the ruthenium-catalyzed iterative C?H amidation of anilides using dioxazolones as an amino source. This strategy could be implemented by the sequential activation of C?H bonds of formerly generated compounds by cascade chelation assistance of newly installed amide groups. Computational studies provided a rationale.
- Park, Juhyeon,Lee, Jia,Chang, Sukbok
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supporting information
p. 4256 - 4260
(2017/04/04)
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- Co(III)-Catalyzed Enaminone-Directed C-H Amidation for Quinolone Synthesis
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We report herein the development of a Co(III)-catalyzed enaminone-directed C-H amidation method for synthetic access to quinolones, an important heterocyclic scaffold for diverse pharmaceutically active structures. The C-H coupling with dioxazolones and subsequent deacylation of an installed amide group allow consecutive C-N coupling generation of quinolones with wide-ranging compatible substituent patterns.
- Shi, Pengfei,Wang, Lili,Chen, Kehao,Wang, Jie,Zhu, Jin
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supporting information
p. 2418 - 2421
(2017/05/12)
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- Rhodium(III)-Catalyzed Directed C?H Amidation of N-Nitrosoanilines and Subsequent Formation of 1,2-Disubstituted Benzimidazoles
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An efficient rhodium-catalyzed direct C?H amidation of N-nitrosoanilines with 1,4,2-dioxazol-5-ones as amidating agents has been developed. This method featured mild reaction conditions, a wide substrate scope and satisfactory yields. Besides, the amidated products could be readily converted to pharmaceutically valuable 1,2-disubstituted benzimidazoles via an HCl-mediated deprotection/cyclization process in one pot.
- Chen, Yanyu,Zhang, Rong,Peng, Qiujun,Xu, Lanting,Pan, XianHua
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supporting information
p. 2804 - 2808
(2017/10/20)
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- Dioxazoles, a new mild nitrene transfer reagent in gold catalysis: Highly efficient synthesis of functionalized oxazoles
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A gold-catalyzed regioselective [3+2] cycloaddition of ynamides with 1,4,2-dioxazoles was developed and offers a novel approach to obtain highly functionalized oxazoles under mild reaction conditions. 1,4,2-Dioxazole was found to act as an efficient N-acyl nitrene equivalent to trigger a facile generation of α-imino gold-carbene intermediate through the elimination of a ketone.
- Chen, Ming,Sun, Ning,Chen, Haoyi,Liu, Yuanhong
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supporting information
p. 6324 - 6327
(2016/05/19)
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- Rh(III)- and Zn(II)-Catalyzed Synthesis of Quinazoline N-Oxides via C-H Amidation-Cyclization of Oximes
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Quinazoline N-oxides have been prepared from simple ketoximes and 1,4,2-dioxazol-5-ones via Rh(III)-catalyzed C-H activation-amidation of the ketoximes and subsequent Zn(II)-catalyzed cyclization. The substrate scope and functional group compatibility were examined. The reaction features relay catalysis by Rh(III) and Zn(II).
- Wang, Qiang,Wang, Fen,Yang, Xifa,Zhou, Xukai,Li, Xingwei
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supporting information
p. 6144 - 6147
(2016/12/09)
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- Site-Selective C–H Amidation of Azobenzenes with Dioxazolones under Rhodium Catalysis
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The rhodium(III)-catalyzed amidation reaction of azobenzenes with dioxazolones is described. This strategy allows the facile and efficient construction of highly substituted ortho-amidated azobenzenes by direct C–H cleavage approach. A wide range of substrates, excellent levels of chemoselectivity as well as high functional-group tolerance were observed. In addition, this protocol was used to generate an array of ortho-amidated ketazines. Further synthetic transformation of amidated azobenzenes furnished a facile construction of benzimidazole and benzotriazole derivatives.
- Mishra, Neeraj Kumar,Oh, Yongguk,Jeon, Mijin,Han, Sangil,Sharma, Satyasheel,Han, Sang Hoon,Um, Sung Hee,Kim, In Su
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supporting information
p. 4976 - 4980
(2016/10/26)
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- Sulfur imidations by light-induced ruthenium-catalyzed nitrene transfer reactions
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N-Acyl nitrenes have been generated from a range of heterocyclic precursors, and their applications in light-induced ruthenium-catalyzed sulfur imidations have been studied. Analyzing the reaction scope and determining the structural requirements of the in situ formed electrophilic nitrogen species for effective nitrene transfer allowed a mechanistic scheme to be proposed. The mechanistic conclusions were substantiated by the identification of potential intermediates.
- Bizet, Vincent,Bolm, Carsten
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supporting information
p. 2854 - 2860
(2015/07/01)
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- Mechanistic Studies on the Rh(III)-Mediated Amido Transfer Process Leading to Robust C-H Amination with a New Type of Amidating Reagent
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Mechanistic investigations on the CpRh(III)-catalyzed direct C-H amination reaction led us to reveal the new utility of 1,4,2-dioxazol-5-one and its derivatives as highly efficient amino sources. Stepwise analysis on the C-N bond-forming process showed th
- Park, Yoonsu,Park, Kyung Tae,Kim, Jeung Gon,Chang, Sukbok
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supporting information
p. 4534 - 4542
(2015/04/22)
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- Study of Sustainability and Scalability in the CpRh(III)-Catalyzed Direct C-H Amidation with 1,4,2-Dioxazol-5-ones
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The practical aspects of CpRh(III)-catalyzed direct C-H amidation with 1,4,2-dioxazol-5-ones were investigated on the operational safety, use of green solvent, and scalability. Differential scanning calorimeter (DSC) measurement showed that 3-phenyl-1,4,2
- Park, Yoonsu,Jee, Soyeon,Kim, Jeung Gon,Chang, Sukbok
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p. 1024 - 1029
(2015/09/01)
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- Optimization and Evaluation of 5-Styryl-Oxathiazol-2-one Mycobacterium tuberculosis Proteasome Inhibitors as Potential Antitubercular Agents
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This is the first report of 5-styryl-oxathiazol-2-ones as inhibitors of the Mycobacterium tuberculosis (Mtb) proteasome. As part of the study, the structure-activity relationship of oxathiazolones as Mtb proteasome inhibitors has been investigated. Furthermore, the prepared compounds displayed a good selectivity profile for Mtb compared to the human proteasome. The 5-styryl-oxathiazol-2-one inhibitors identified showed little activity against replicating Mtb, but were rapidly bactericidal against nonreplicating bacteria. (E)-5-(4-Chlorostyryl)-1,3,4-oxathiazol-2-one) was most effective, reducing the colony-forming units (CFU)/mL below the detection limit in only seven days at all concentrations tested. The results suggest that this new class of Mtb proteasome inhibitors has the potential to be further developed into novel antitubercular agents for synergistic combination therapies with existing drugs.
- Russo, Francesco,Gising, Johan,?kerbladh, Linda,Roos, Annette K.,Naworyta, Agata,Mowbray, Sherry L.,Sokolowski, Anders,Henderson, Ian,Alling, Torey,Bailey, Mai A.,Files, Megan,Parish, Tanya,Karlén, Anders,Larhed, Mats
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p. 342 - 362
(2015/06/30)
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- Comparative Catalytic Activity of Group 9 [CpMIII] Complexes: Cobalt-Catalyzed C-H Amidation of Arenes with Dioxazolones as Amidating Reagents
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A procedure for the [CpCoIII]-catalyzed direct C-H amidation of arenes with dioxazolone has been developed. This reaction proceeds under straightforward and mild conditions with a broad range of substrates, including anilides. A comparative study on the catalytic activity of Group 9 [{CpMCl2}2] complexes revealed the unique efficiency of the cobalt catalyst. Pick of the bunch: A variety of arenes, including anilides, underwent direct C-H amidation with dioxazolones in the presence of a cobalt catalyst with a Cp? ligand under mild and straightforward reaction conditions (see scheme; Piv=pivaloyl). A comparative study of Group 9 [CpMIII] complexes revealed the unique ability of the cobalt catalyst to promote this transformation efficiently.
- Park, Juhyeon,Chang, Sukbok
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supporting information
p. 14103 - 14107
(2016/01/25)
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- Light-induced ruthenium-catalyzed nitrene transfer reactions: A photochemical approach towards N-Acyl sulfimides and sulfoximines
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1,4,2-Dioxazol-5-ones are five-membered heterocycles known to decarboxylate under thermal or photochemical conditions, thus yielding N-acyl nitrenes. Described herein is a light-induced ruthenium-catalyzed N-acyl nitrene transfer to sulfides and sulfoxides by decarboxylation of 1,4,2-dioxazol-5-ones at room temperature, thus providing direct access to N-acyl sulfimides and sulfoximines under mild reaction conditions. In addition, a one-pot sulfur imidation/oxidation sequence catalyzed by a single ruthenium complex is reported. Double duty: A one-pot sulfur imidation/oxidation sequence using a single ruthenium complex for both steps was developed (see scheme). Photochemical decarboxylations of 1,4,2-dioxazol-5-ones provide N-acyl nitrenes, which imidate sulfides at ambient temperature. The subsequent oxidation then occurs under mild phase-transfer catalysis conditions. In this manner, N-acyl sulfimides and sulfoximines can be obtained in high yields starting from sulfides.
- Bizet, Vincent,Buglioni, Laura,Bolm, Carsten
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supporting information
p. 5639 - 5642
(2014/06/10)
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- Design, synthesis and evaluation of D,D-peptidase and beta-lactamase inhibitors: Azapeptides, oxapeptides and related heterocycles
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Reactive molecules susceptible to form stable acyl enzyme intermediates with D,D-peptidases and β-lactamases were designed as potential irreversible inhibitors of Penicillin Sensitive Enzymes (PSEs). The structures examined were a series of azapeptides and oxapeptides, both analogs of the D-Ala-D-Ala substrate, and some heterocycles, such as imidazolidinones and oxazolidinones, both analogs of the β-lactam antibiotics. The various strategies investigated for their synthesis are described and discussed. Some biological results are reported.
- Marchand-Brynaert,Mougenot,Combret,Belotti,Guillot,Ghosez
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p. 455 - 469
(2007/10/02)
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