1027340-27-7Relevant academic research and scientific papers
Design and synthesis of mycobacterial pks13 inhibitors: Conformationally rigid tetracyclic molecules
Zhang, Wei,Liu, Ling-ling,Lun, Shichun,Wang, Shuang-Shuang,Xiao, Shiqi,Gunosewoyo, Hendra,Yang, Fan,Tang, Jie,Bishai, William R.,Yu, Li-Fang
, (2021/02/03)
We previously reported a series of coumestans?a naturally occurring tetracyclic scaffold containing a δ-lactone?that effectively target the thioesterase domain of polyketide synthase 13 (Pks13) in Mycobacterium tuberculosis (Mtb), resulting in superior an
Optimizing ligand structure for low-loading and fast catalysis for alkynyl-alcohol and-amine cyclization
Stubbs, James M.,Bridge, Benjamin J.,Blacquiere, Johanna M.
, p. 7928 - 7937 (2019/06/13)
A series of [Ru(Cp/Cp?)(PR2NR′2)(MeCN)]PF6 complexes were prepared, in which the steric and electronic properties of the primary coordination sphere were varied (R = Ph, t-Bu, Bn; and Cp vs. Cp?). These complexes were catalytically active in the cyclization of alkyne substrates with an intramolecular nucleophile (amine or alcohol) to produce 5-and 6-membered heterocycles. The effect of the 1° coordination sphere structure on catalyst performance was evaluated. Steric bulk around the metal centre was a key feature to achieve rapid catalysis at low temperatures. The catalyst [Ru(Cp)(Pt-Bu2NPh2)(MeCN)]PF6 gave a turnover number that was >1 order of magnitude more active than previous catalysts in the cyclization of the benchmark substrate 2-ethynylaniline. This catalyst is tolerant of a diversity of functional groups and is competent at the formation of various substituted indoles.
Copper-Catalyzed Tandem Cross-Coupling/[2 + 2] Cycloaddition of 1,6-Allenynes with Diazo Compounds to 3-Azabicyclo[5.2.0] Ring Systems
He, Min,Chen, Nuan,Zhou, Ting,Li, Qing,Li, Hongguang,Lang, Ming,Wang, Jian,Peng, Shiyong
supporting information, p. 9559 - 9563 (2019/11/21)
An unprecedented copper-catalyzed tandem cross-coupling/[2 + 2] cycloaddition of 1,6-allenynes with diazo compounds was reported, chemo- and regioselectively providing 3-azabicyclo[5.2.0] frameworks in moderate to excellent yields under mild reaction conditions. Moreover, the products readily convert to highly functionalized quinolines via oxidative radical rearrangement.
Synthesis of 2-(Trifluoromethyl)indoles via Domino Trifluoromethylation/Cyclization of 2-Alkynylanilines
Ye, Yibin,Cheung, Kelvin Pak Shing,He, Lisi,Tsui, Gavin Chit
supporting information, p. 1676 - 1679 (2018/03/23)
A new method for the synthesis of 2-(trifluoromethyl)indoles using easily accessible 2-alkynylanilines and a well-established fluoroform-derived CuCF3 reagent is described. This method utilizes a domino trifluoromethylation/cyclization strategy
Revisiting the Gold-Catalyzed Dimerization of 2-Ethynylanilines: A Room-Temperature and Silver-Free Protocol for the Synthesis of Multifunctional Quinolines
Praveen, Chandrasekar,Perumal
, p. 855 - 864 (2016/03/15)
A room temperature and silver-free protocol for the formation of quinolines from 2-ethynylanilines through a dimerization event was achieved using a dinuclear gold catalyst, Au2(BIPHEP)(NTf2)2. The reaction is inherently modular, allowing for the incorporation of peripheral substituents at any site of the quinoline product. The reaction is readily applied to other heterocyles also as exemplified by the preparation of naphthyridines. Competition reactions to determine the reactivity of dissimilar alkynes demonstrated that the product ratio of dimerization vs intermolecular addition is rather dependent on the electronic nature of aryl substituent on the alkynes. However, control experiments with substrates possessing internal alkynes resulted in cycloisomerization instead of expected dimerization, which is indicative of possible steric influence of the alkyne terminus in the reaction outcome.
Pd/C-catalyzed cyclizative cross-coupling of two ortho-alkynylanilines under aerobic conditions: Synthesis of 2,3′-bisindoles
Yao, Bo,Wang, Qian,Zhu, Jieping
supporting information, p. 7413 - 7416 (2015/05/13)
Abstract A palladium-catalyzed cyclizative cross-coupling of two o-alkynylanilines to 2,3′-bisindoles under aerobic oxidative conditions was developed. Mechanistic studies suggested that the two catalytic cycles, namely the formation of 3-alkynylindoles 8
Copper-catalyzed annulation of α-substituted diazoacetates with 2-ethynylanilines: The direct synthesis of C2-functionalized indoles
Liu, Gang,Xu, Guangyang,Li, Jian,Ding, Dong,Sun, Jiangtao
supporting information, p. 1387 - 1390 (2014/03/21)
Copper-catalyzed direct annulation of α-substituted diazoacetates with 2-ethynylanilines leading to C2-functionalized indoles was achieved under mild reaction conditions. The C2-(carboxylate methyl) substituted indoles were obtained in moderate to high yi
Copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N, O -acetal leading to construction of quinoline derivatives
Sakai, Norio,Tamura, Kosuke,Shimamura, Kazuyori,Ikeda, Reiko,Konakahara, Takeo
supporting information; experimental part, p. 836 - 839 (2012/04/05)
A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a C1 part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2/
