7505-92-2Relevant academic research and scientific papers
Amine-Mediated Bond Cleavage in Oxidized Lignin Models
Li, Hongji,Liu, Meijiang,Liu, Huifang,Luo, Nengchao,Zhang, Chaofeng,Wang, Feng
, p. 4660 - 4665 (2020/07/04)
Introducing amines/ammonia into lignin cracking will allow novel bond cleavage pathways. Herein, a method of amines/ammonia-mediated bond cleavage in oxidized lignin β-O-4 models was studied using a copper catalyst at room temperature, demonstrating the effect of the amine source on the selectivity of products. For primary and secondary aliphatic amines, lignin ketone models underwent oxidative Cα?Cβ bond cleavage and Cα?N bond formation to generate aromatic amides. For ammonia, the competition between oxygen and ammonia determined the selectivity between Cα?N and Cβ?N bond formation, generating amides and α-keto amides, respectively. For tertiary amines, the lignin models underwent oxidative Cα?Cβ bond cleavage to benzoic acids. Control experiments indicated that amines act as nucleophiles attacking at the Cα or Cβ position of the oxidized β-O-4 linkage to be cleaved. This study represents a novel example that the breakage of oxidized lignin model can be regulated by amines with a copper catalyst.
Oxidative Coupling of Diazo and NH4I: A Route to Primary Oxamates and α-Ketoamides
Fang, Shangwen,Li, Jingjing,Wan, Xiaobing,Wang, Hanghang,Zhao, Yanwei,Zheng, Yonggao
supporting information, p. 3050 - 3058 (2020/03/23)
A simple and efficient method has been developed for the preparation of primary oxamates and α-ketoamides through the oxidative coupling of diazo compounds and NH4I. Under the optimized reaction conditions, a range of diazoesters and α-diazoketones was explored, and the corresponding products were obtained in moderate to good yields. This protocol is metal-free, is performed under mild conditions, has a wide substrate scope, and offers operational simplicity.
1,2-dicarbonyl compound and synthesis method thereof
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Paragraph 0055-0060, (2019/10/01)
The invention discloses a method for synthesizing a 1,2-dicarbonyl compound (1,2-dicarbonylamide or alpha-diketone compound), wherein 1,2-dicarbonyl thioester compounds used as 1,2-dicarbonyl reagentsreact with amine compounds or boric anhydride compounds under appropriate conditions to respectively synthesize a series of 1,2-dicarbonyl compounds. According to the present invention, the 1,2-dicarbonyl compound is obtained by using the stable 1,2-dicarbonyl thioester compound as the dicarbonylation reagent through one-step construction under mild conditions, such that the disadvantage that thetraditional method uses the unstable alpha-carbonyl acyl chloride to synthesize the 1,2-dicarbonyl compound is avoided.
I2/PhI(OAc)2 Copromoted Amination Reaction: Synthesis of α-Dicarbonylsulfoximine Derivatives by Incorporating an Intact Dimethyl Sulfoxide
Zhao, Peng,Wu, Xia,Geng, Xiao,Wang, Can,Zhou, You,Wu, Yan-Dong,Wu, An-Xin
, p. 8322 - 8329 (2019/06/27)
An I2/PhI(OAc)2 copromoted strategy using dimethyl sulfoxide as an "S/C2/O" source for preparing α-dicarbonylsulfoximine derivatives is reported. This process involves oxidative coupling to construct a C-N bond and electrophilic amin
Green preparation method of alpha-keto-amide
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Paragraph 0020-0022, (2019/10/15)
The invention discloses a method for preparing alpha-keto-amide. The method takes alpha-diazo-ketones compound and ammonium iodide as reaction substrates, under the condition of transition metal-freeand alkali-free, takes tert-butyl hydroperoxide (TBHP) a
Cu-Mediated Stereoselective [4+2] Annulation between N-Hydroxybenzimidoyl Cyanide and Norbornene
Liu, Kui,Chen, Zhen-Bang,Zhang, Fang-Ling,Qian, Chun,Tao, Shou-Wei,Xu, Qiong-Ming,Zhu, Yong-Ming
, p. 8457 - 8463 (2018/06/25)
A Cu-mediated stereoselective [4+2] annulation between N-hydroxybenzimidoyl cyanides and norbornene (NBE) has been developed for the synthesis of 4H-1,2-oxazin-4-ones. The reaction proceeds through sequentially forming C-O/C-C bonds. The advantage of this reaction includes high stereoselectivity, excellent yields, as well as simple and mild reaction conditions. A total of 26 examples are presented along with some control experiments.
UV Assisted High-Efficient Synthesis of α-Ketoamides using Air Promoted by A Non-Metal Catalyst in Aqueous Solution
Li, Jianhui,He, Shaopo,Zhang, Kuan,Quan, Ziyi,Shan, Qiheng,Sun, Zhongliang,Wang, Bo
, p. 4868 - 4873 (2018/10/15)
Presented here is the first example of UV (λ=210 nm) promoted procedure proceeding in aqueous media at room temperature using ambient air as the oxidant for efficient synthesis of an array of α-ketoamides of all types using a non-metal catalyst N-iodosuccinimide with a loading of 20 mol%. With UV, oxygen in the air was efficiently utilized as the green oxidant, some control experiments were carried out and a plausible mechanism was proposed, disclosing that in aqueous solution, the oxidation process was actually triggered by dioxygen radical anion (O2.?), while not molecular oxygen. A variety of secondary amines and primary amines as well as ammonia were employed as the amine moieties, and the desired product primary-, secondary-, and tertiary α-ketoamides were afforded in good to excellent yields of up to 96 %.
Selective Cleavage of Inert Aryl C-N Bonds in N-Aryl Amides
Zhang, Zhiguo,Zheng, Dan,Wan, Yameng,Zhang, Guisheng,Bi, Jingjing,Liu, Qingfeng,Liu, Tongxin,Shi, Lei
, p. 1369 - 1376 (2018/02/09)
A highly selective, IBX-promoted reaction has been developed for the oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions (HFIP/H2O, 25 °C), providing facile access to various useful primary amides, some of which would be otherwise unattainable using conventional aminolysis and hydrolysis approaches.
Novel synthesis of tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones via decarboxylative cyclization reaction of α-amino acids and α-ketoamides
Wu, Jia-shou,Jiang, Hua-jiang,Yang, Jian-guo,Jin, Zheng-neng,Chen, Ding-ben
, p. 546 - 551 (2017/01/16)
An efficient and practical method was developed for the synthesis of tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones based on the decarboxylative cyclization reaction of α-ketoamides and proline. In most cases, tetrahydro-1H-pyrrolo[1,2-a]imidazol-2-ones were obtained with perfect diastereoselectivity to give trans-isomer in excellent yield.
nBu4NI-Mediated oxidation of methyl ketones to α-ketoamides: using ammonium, primary and secondary amine-salt as an amine moiety
Wang, Dan,Zhang, Kuan,Jia, Luhan,Zhang, Danting,Zhang, Yue,Cheng, Yujia,Lin, Chang,Wang, Bo
, p. 3427 - 3434 (2017/04/24)
Presented here is the first example of synthesizing an array of primary-, secondary-, and tertiary-α-ketoamides with a non-metal catalyst nBu4NI from methyl ketones and inexpensive readily available amine/ammonium salts; the reactions proceeded smoothly under mild conditions, TBHP was used as an oxidant and the corresponding α-ketoamides were afforded in moderate to excellent yields.
