61403-29-0Relevant academic research and scientific papers
DISUBSTITUTED ALKYNE DERIVATIVES
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Page/Page column 147-148, (2020/07/14)
The present invention relates to disubstituted alkyne derivatives. These compounds are useful for the prevention and/or treatment of several medical conditions including hyperproliferative disorders and diseases.
Photoinduced synthesis of fluorinated dibenz[: B, e] azepines via radical triggered cyclization
Qi, Xu-Kuan,Zhang, Hong,Pan, Zi-Tong,Liang, Rong-Bin,Zhu, Can-Ming,Li, Jing-Hong,Tong, Qing-Xiao,Gao, Xue-Wang,Wu, Li-Zhu,Zhong, Jian-Ji
supporting information, p. 10848 - 10851 (2019/09/18)
A simple, mild and efficient approach to access fluorinated dibenz[b,e]azepines via visible-light photoredox catalysis is presented. Inexpensive and commercially available fluoroalkyl anhydrides in concert with pyridine N-oxide are employed as the source
Enantioselective A3-Coupling Reaction Employing Chiral CuI-i PrpyboxdiPh/ N-Boc-(l)-Proline Complex under Cooperative Catalysis: Application in the Synthesis of (Indol-2-yl)methanamines
Dhanasekaran, Sivasankaran,Kannaujiya, Vinod. K.,Biswas, Rayhan G.,Singh, Vinod K.
, p. 3275 - 3292 (2019/03/11)
An efficient route to enantioenriched propargylamines via a three-component alkynylation reaction using cooperative catalysis with a CuI-iPrpyboxdiPh complex and N-Boc-(l)-proline has been accomplished. A variety of functionalized amines, aldehydes, and 2-ethynyl anilines were reacted smoothly at ambient temperature to furnish a wide range of propargylamines in high yields (up to 94%) and excellent enantioselectivities (up to 98% ee). Synthetic utility of the methodology has been demonstrated by transforming the products into various synthetically useful intermediates. Finally, propargylamines were transformed into biologically important (indol-2-yl)methanamines over two steps in good yields (up to 88%) with an excellent level of enantioselectivities (up to 95%).
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.
PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles
Chaisan, Nattawadee,Kaewsri, Wilailak,Thongsornkleeb, Charnsak,Tummatorn, Jumreang,Ruchirawat, Somsak
, p. 675 - 680 (2018/01/18)
An efficient synthesis of N-acetyl-2-substituted indole derivatives via direct intramolecular hydroamination of N-acetyl-2-alkynylaniline derivatives was developed. The reaction could be applied to a wide range of substrates employing only 1–2 mol% of PtCl4 as the catalyst to furnish the desired indole products in moderate to excellent yields. The current protocol is efficient, reliable and scalable, and could serve as an important tool for convenient and rapid access to this important class of N-heterocyclic skeleton from readily available substrates.
Hydroformylation of 2-Alkynylanilines: Toward an Alternative Methodology for the Synthesis of 3-Substituted Indoles
Holzapfel, Cedric,Dasilva, Etelinda,Den Drijver, Laetitia,Bredenkamp, Tyler
, p. 2912 - 2915 (2016/09/28)
A potentially viable route for the synthesis of 3-substituted indoles is presented herein. The methodology is based on a regioselective Rh-catalysed hydroformylation of prepared 2-alkyn-1-ylanilines. The requisite 2-alkynylaniline substrates were prepared in high yields (>85 %) using the Pd-catalysed Sonogashira reaction. A catalyst complex that comprises RhI(CO)(PPh3)3 and 1,2-bis(diphenylphosphino)ethane as the ligand allowed the quantitative conversions of the alkynyl substrates with selectivities >75 % for the desired 3-substituted indoles.
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
, 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
Rh(III)- and Ir(III)-Catalyzed C-H alkynylation of arenes under chelation assistance
Xie, Fang,Qi, Zisong,Yu, Songjie,Li, Xingwei
supporting information, p. 4780 - 4787 (2014/04/17)
An efficient Rh(III)- and Ir(III)-catalyzed, chelation-assisted C-H alkynylation of a broad scope of (hetero)arenes has been developed using hypervalent iodine-alkyne reagents. Heterocycles, N-methoxy imines, azomethine imines, secondary carboxamides, azo compounds, N-nitrosoamines, and nitrones are viable directing groups to entail ortho C-H alkynylation. The reaction proceeded under mild conditions and with controllable mono- and dialkynylation selectivity when both mono- and dialkynylation was observed. Rh(III) and Ir(III) catalysts exhibited complementary substrate scope in this reaction. The synthetic applications of the coupled products have been demonstrated in subsequent derivatization reactions. Some mechanistic studies have been conducted, and two Rh(III) complexes have been established as key reaction intermediates. The current C-H alkynylation system complements those previously reported under gold or palladium catalysis using hypervalent iodine reagents.
Cesium carbonate-promoted hydroamidation of alkynes: Enamides, indoles and the effect of iron(III) chloride
Herrero, Maria Teresa,De Sarralde, Jokin Diaz,Sanmartin, Raul,Bravo, Laura,Dominguez, Esther
supporting information, p. 3054 - 3064 (2013/01/15)
A series of enamide derivatives was prepared by a simple procedure for the hydroamidation of alkynes with amides and sulfonamides. The use of such a mild base as cesium carbonate promotes the latter transformation, and the addition of catalytic amounts of iron(III) chloride has a beneficial effect in the outcome of some of the presented hydroamidation reactions. A range of indoles was also synthesized from ortho-alkynylanilides by both complementary procedures, which proved to be useful for the construction of the indolo[1,2-c]quinazoline tetracyclic system from an ortho-(2-aminophenylalkynyl)anilide. Copyright
