14677-99-7Relevant articles and documents
Synthesis and biological evaluation of 4-aryl-5-cyano-2H-1,2,3-triazoles as inhibitor of HER2 tyrosine kinase
Cheng, Zhi-Yi,Li, Wen-Jie,He, Feng,Zhou, Jun-Min,Zhu, Xiao-Feng
, p. 1533 - 1538 (2007)
4-Aryl-5-cyano-2H-1,2,3-triazoles bearing a variety of substituting groups on 4-phenyl were synthesized. The chemicals, designed as HER2 tyrosine kinase inhibitors, were screened for bioactivity of inhibiting growth of breast cancer MDA-MB-453 cells. The
One-pot synthesis of conjugated alkynenitriles from aldehydes
Kim, Joong-Gon,Lee, Eun Hwa,Jang, Doo Ok
, p. 2299 - 2301 (2007)
A method of preparing conjugated alkynenitriles was developed from various aldehydes with CCl3CN and PPh3 in the presence of tBuLi. The reaction proceeded via α-chlorovinyl nitrile as an intermediate without any side react
Additive-Controlled Switchable Selectivity from Cyanobenzenes to 2-Alkynylpyridines: Ruthenium(II)-Catalyzed [2+2+2] Cycloadditions of Diynes and Alkynylnitriles
Bhatt, Divya,Patel, Neha,Chowdhury, Hrishikesh,Bharatam, Prasad V.,Goswami, Avijit
, p. 1876 - 1882 (2018)
A highly efficient additive-dependent chemoselective protocol for the synthesis of fused cyanoarenes and 2-alkynylpyridines has been developed by the reaction of 1,6-diynes with alkynylnitriles using chloro(pentamethylcyclopentadienyl) (cyclooctadiyne)ruthenium(II) as catalyst in dimethoxyethane (DME). The course of the reaction can be drastically altered simply by adding a catalytic amount of AgOTf as an additive resulting in a comprehensive shift in product formation from cyanoarenes to 2-alkynylpyridines. Theoretical studies clearly indicate that the neutral Ru-complex is responsible for the formation of cyanobenzenes, whereas the in situ generated cationic Ru-complex plays a crucial role in the 2-alkynylpyridines formation. (Figure presented.).
Enantioselective Nickel-Catalyzed Alkyne-Azide Cycloaddition by Dynamic Kinetic Resolution
Liu, En-Chih,Topczewski, Joseph J.
, p. 5308 - 5313 (2021/05/04)
The triazole heterocycle has been widely adopted as an isostere for the amide bond. Many native amides are α-chiral, being derived from amino acids. This makes α-N-chiral triazoles attractive building blocks. This report describes the first enantioselective triazole synthesis that proceeds via nickel-catalyzed alkyne-azide cycloaddition (NiAAC). This dynamic kinetic resolution is enabled by a spontaneous [3,3]-sigmatropic rearrangement of the allylic azide. The 1,4,5-trisubstituted triazole products, derived from internal alkynes, are complementary to those commonly obtained by the related CuAAC reaction. Initial mechanistic experiments indicate that the NiAAC reaction proceeds through a monometallic Ni complex, which is distinct from the CuAAC manifold.
Chemo- And regioselective click reactions through nickel-catalyzed azide-alkyne cycloaddition
Baek, Seung-Yeol,Baik, Mu-Hyun,Choe, Wonyoung,Hong, Sung You,Jeon, Ji Hwan,Jeong, Seo Yeong,Kim, Woo Gyum,Nam, Dongsik
, p. 3374 - 3381 (2020/05/14)
Metal-catalyzed cycloaddition is an expeditious synthetic route to functionalized heterocyclic frameworks. However, achieving reactivity-controlled metal-catalyzed azide-alkyne cycloadditions from competing internal alkynes has been challenging. Herein, we report a nickel-catalyzed [3 + 2] cycloaddition of unsymmetrical alkynes with organic azides to afford functionalized 1,2,3-triazoles with excellent regio- and chemoselectivity control. Terminal alkynes and cyanoalkynes afford 1,5-disubstituted triazoles and 1,4,5-trisubstituted triazoles bearing a 4-cyano substituent, respectively. Thioalkynes and ynamides exhibit inverse regioselectivity compared with terminal alkynes and cyanoalkynes, affording 1,4,5-trisubstituted triazoles with 5-thiol and 5-amide substituents, respectively. Density functional theory calculations are performed for the elucidation of the reaction mechanism. The computed mechanism suggests that a nickellacyclopropene intermediate is generated by the oxidative addition of the alkyne substrate to the Ni(0)-Xantphos catalyst, and the subsequent C-N coupling of this intermediate with an azide is responsible for the chemo- and regioselectivity.
Palladium-Catalyzed Nitrile-Assisted C(sp3)-Cl Bond Formation for Synthesis of Dichlorides
He, Dandan,Huang, Liangbin,Li, Jianxiao,Wu, Wanqing,Jiang, Huanfeng
, p. 8308 - 8311 (2019/10/16)
A palladium-catalyzed coupling procedure of alkenes with alkynylnitriles has been demonstrated for the synthesis of dichlorides. The reaction is the first example of nitrile-assisted C(sp3)-Cl formation promoted by coordination of a cyano group with an alkylpalladium(II) complex. The construction of a five-membered cycle intermediate successfully inhibits the β-hydride abstraction, resulting in direct C-Cl bond reductive elimination of alkylpalladium(II) chloride.
Copper-catalyzed direct cyanation of terminal alkynes with benzoyl cyanide
Du, Yan,Li, Zheng
supporting information, p. 4622 - 4625 (2018/11/27)
Copper-catalyzed direct cyanation of terminal alkynes is achieved using less toxic, stable and easy to handle benzoyl cyanide as a cyanide source and air as an oxidant. This protocol provides a good alternative to the preparation of 3-arylpropiolonitriles
Synthesis of 1-Cyanoalkynes and Their Ruthenium(II)-Catalyzed Cycloaddition with Organic Azides to Afford 4-Cyano-1,2,3-triazoles
Liu, Peiye,Clark, Ronald J.,Zhu, Lei
, p. 5092 - 5103 (2018/05/15)
A new method to convert terminal alkynes under relatively mild conditions to 1-cyanoalkynes using in situ formed cyanogen is described. 1-Cyanoalkynes have a higher reactivity than terminal alkynes in the ruthenium(II)-catalyzed regiospecific azide-alkyne cycloaddition to afford 4-cyano-1,2,3-triazoles. A mechanistic proposal different from the one that terminal alkynes adopt under the same reaction conditions is proposed. This work provides a new and convenient two-step sequence to prepare 4-cyano-1,2,3-triazoles from terminal alkynes and organic azides.
Silver-Mediated Direct C-H Cyanation of Terminal Alkynes with N-Isocyanoiminotriphenylphosphorane
Wang, Hannan,Mi, Pengbing,Zhao, Wanjun,Kumar, Ravi,Bi, Xihe
supporting information, p. 5613 - 5616 (2017/10/25)
A direct cyanation of terminal alkynes for the synthesis of propionitrile derivatives, with the aid of silver salt using water additive, has been achieved. The cyano source used is N-isocyanoiminotriphenylphosphorane, which is nontoxic, safe, and easy to handle. This protocol is characterized by its operational simplicity, high efficiency with excellent yields, broad substrate scope, and greater functional group tolerance.
3-ARYL PROPIOLONITRILE COMPOUNDS FOR THIOL LABELING
-
, (2016/06/13)
The present invention relates to a process for labeling compounds comprising thiol moieties with 3-arylpropiolonitrile compounds, to 3-arylpropiolonitrile compounds substituted with tag moieties and to specific 3-arylpropiolonitrile linkers.