104-97-2Relevant articles and documents
Synthesis and Evaluation of 1,3,4-Thiadiazole Derivatives Containing Cyclopentylpropionamide as Potential Antibacterial Agent
Zhang, Min,Xu, Weiming,Wei, Kun,Liu, Hongwu,Yang, Qin,Liu, Qin,Yang, Liyun,Luo, Yuqin,Xue, Wei
, (2019)
This study aimed to identify new strategies for the control of these plant bacterial diseases by combining a pharmacophoric group of different bioactive compounds. A series of 3-cyclopentylpropionamide containing 1,3,4-thiadiazole derivatives was synthesized and characterized via 1H-NMR, 13C-NMR, and HRMS. Bioassay results indicated that compounds 7a, 7d, 7j, 7m, 7n, and 7s had excellent antibacterial activity compared with the positive control. Among them, compound 7a exhibited remarkable inhibitory effect against Xoo with an EC50 of 21.41?μg/mL, which surpassed that of thiodiazole copper (67.71?μg/mL) and bismerthiazol (69.05?μg/mL). Greenhouse condition tests further revealed that 7a had approximately equal curative activity and better protection activity (41.58%) against bacterial leaf blight of rice than that of thiodiazole copper and bismerthiazol (46.86 and 42.25%, respectively). Structure–activity relationship analysis exhibited that sulfone fragment favored inhibition. Overall, this study suggested that derivatives containing 1,3,4-thiadiazole 3-cyclopentylpropanamide can be used as new lead compounds for bactericide studies.
Remote Regioselective Radical C-H Functionalization of Unactivated C-H Bonds in Amides: The Synthesis of gem-Difluoroalkenes
Hu, Qu-Ping,Cheng, Jing,Wang, Ying,Shi, Jie,Wang, Bi-Qin,Hu, Ping,Zhao, Ke-Qing,Pan, Fei
, p. 4457 - 4462 (2021)
The site-selective functionalization of unactivated aliphatic amines is an attractive and challenging synthetic approach. We herein report a general strategy for the remote site-selective functionalization of unactivated C(sp3)-H bonds in amides by photogenerated amidyl radicals to form gem-difluoroalkenes with trifluoromethyl-substituted alkenes. The site selectivity is controlled by a 1,5-hydrogen atom transfer (HAT) process of the amide. This photocatalyzed transformation shows both chemo- and site-selectivity, facilitating the formation of a secondary, tertiary, or quaternary carbon center.
Design and Synthesis of 2-Methyl-7-aminobenzoxazole as Auxiliary in the Palladium(II)-Catalyzed Arylation of a beta-Positioned C(sp3)-H Bond
Luo, Feihua,Yang, Jun,Li, Zhengkai,Xiang, Haifeng,Zhou, Xiangge
, p. 887 - 893 (2016)
A palladium(II)-catalyzed direct arylation of methylene C(sp3)-H bonds by 2-methyl-7-aminobenzoxazole as an effective auxiliary is reported. This process exhibited high beta-site selectivity, broad substrate scope, and compatibility with different functional groups with moderate to high yields up to 89%.
Cationic lipid compound, composition containing same and application
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Paragraph 0103, (2021/06/22)
The invention provides a cationic lipid compound, a composition containing the cationic lipid compound and application of the cationic lipid compound. In order to provide more choices for delivery of preparations such as nucleic acid drugs, gene vaccines, small molecule drugs and the like, the invention provides a cationic lipid compound shown in the general formula or pharmaceutically available salts thereof. The cationic lipid compound provided by the invention can be used for delivering DNA, RNA or small molecule drugs, enriches the types of cationic lipid compounds, and has important significance for the development and application of nucleic acid preventive and therapeutic agents.
Remote Directed Isocyanation of Unactivated C(sp3)-H Bonds: Forging Seven-Membered Cyclic Ureas Enabled by Copper Catalysis
Zhang, Hongwei,Tian, Peiyuan,Ma, Lishuang,Zhou, Yulu,Jiang, Cuiyu,Lin, Xufeng,Xiao, Xiao
supporting information, p. 997 - 1002 (2020/02/15)
Reported herein is an unprecedented copper-catalyzed site-selective ?-C(sp3)-H bonds activation of aliphatic sulfonamides for constructing the synthetically useful seven-membered N-heterocycles. A key to success is the use of in-situ-formed amide radicals, to activate the inert C(sp3)-H bond, and inexpensive TMSNCO, as a coupling reagent under mild conditions. To the best of our knowledge, this represents the first use of alkylamine derivatives as a five-membered synthon to prepare a seven-membered N-heterocycles.
Copper-Catalyzed Amide Radical-Directed Cyanation of Unactivated Csp3-H Bonds
Zhang, Hongwei,Zhou, Yulu,Tian, Peiyuan,Jiang, Cuiyu
supporting information, (2019/03/19)
A method for site-selective intermolecular δ/?-Csp3-H cyanation of aliphatic sulfonamides is developed using TsCN as the cyanating reagent, catalyzed by a Cu(I)/phenanthroline complex. The mild, expeditious, and modular protocol allows efficient remote Csp3-H cyanation with good functional group tolerance and high regioselectivity. Mechanistic studies indicate that the reaction might proceed through a Cu(I)-mediated N-F bond cleavage to generate an amidyl radical, 1,5-HAT, and cyano group transfer of the resulting carbon radical with TsCN.
Synthesis of Ynolates via Double Deprotonation of Nonbrominated Esters
Sun, Jun,Yoshiiwa, Toshiya,Iwata, Takayuki,Shindo, Mitsuru
supporting information, p. 6585 - 6588 (2019/09/30)
Herein, we report a double deprotonation method used for the preparation of ynolates starting from nonbrominated 2,6-di-tert-butylphenyl esters. The current method is superior to the previously described double lithium/halogen exchange approach because easily accessible starting materials are used. This method will be especially useful for preparation of ynolates bearing functional groups in organic synthesis.
Non- C2-Symmetric Chiral-at-Ruthenium Catalyst for Highly Efficient Enantioselective Intramolecular C(sp3)-H Amidation
Zhou, Zijun,Chen, Shuming,Hong, Yubiao,Winterling, Erik,Tan, Yuqi,Hemming, Marcel,Harms, Klaus,Houk,Meggers, Eric
supporting information, p. 19048 - 19057 (2019/12/04)
A new class of chiral ruthenium catalysts is introduced in which ruthenium is cyclometalated by two 7-methyl-1,7-phenanthrolinium heterocycles, resulting in chelating pyridylidene remote N-heterocyclic carbene ligands (rNHCs). The overall chirality results from a stereogenic metal center featuring either a or Δabsolute configuration. This work features the importance of the relative metal-centered stereochemistry. Only the non-C2-symmetric chiral-at-ruthenium complexes display unprecedented catalytic activity for the intramolecular C(sp3)-H amidation of 1,4,2-dioxazol-5-ones to provide chiral -lactams with up to 99:1 er and catalyst loadings down to 0.005 mol % (up to 11 ?200 TON), while the C2-symmetric diastereomer favors an undesired Curtius-type rearrangement. DFT calculations elucidate the origins of the superior C-H amidation reactivity displayed by the non-C2-symmetric catalysts compared to related C2-symmetric counterparts.
Primary, Secondary, and Tertiary γ-C(sp3)-H Vinylation of Amides via Organic Photoredox-Catalyzed Hydrogen Atom Transfer
Chen, Hui,Guo, Liangliang,Yu, Shouyun
supporting information, p. 6255 - 6259 (2018/10/05)
An efficient strategy for primary, secondary and tertiary aliphatic γ-C(sp3)-H vinylation of amides with alkenylboronic acids is reported. These reactions are catalyzed by visible-light organic photoredox agents. Regioselective γ-C(sp3)-H vinylation of amides is controlled by a 1,5-hydrogen atom transfer of an amidyl radical generated in situ.
Selective α-Oxyamination and Hydroxylation of Aliphatic Amides
Li, Xinwei,Lin, Fengguirong,Huang, Kaimeng,Wei, Jialiang,Li, Xinyao,Wang, Xiaoyang,Geng, Xiaoyu,Jiao, Ning
supporting information, p. 12307 - 12311 (2017/09/11)
Compared to the α-functionalization of aldehydes, ketones, even esters, the direct α-modification of amides is still a challenge because of the low acidity of α-CH groups. The α-functionalization of N?H (primary and secondary) amides, containing both an unactived α-C?H bond and a competitively active N?H bond, remains elusive. Shown herein is the general and efficient oxidative α-oxyamination and hydroxylation of aliphatic amides including secondary N?H amides. This transition-metal-free chemistry with high chemoselectivity provides an efficient approach to α-hydroxy amides. This oxidative protocol significantly enables the selective functionalization of inert α-C?H bonds with the complete preservation of active N?H bond.
