52839-45-9Relevant academic research and scientific papers
Harnessing the reactivity of Ortho-formyl-arylketones: Base-promoted regiospecific synthesis of functionalized isoquinolines
Mishra, Pawan K.,Verma, Shalini,Kumar, Manoj,Kumar, Ankit,Verma, Akhilesh K.
supporting information, p. 8278 - 8281 (2019/07/16)
An efficient and base-mediated one-pot regiospecific synthesis of structurally diversified isoquinolines and benzo[h] isoquinolines from easily accessible ortho-formyl-arylketones and aryl/(het)arylmethanamines has been described. Challenging 3-alkynyl/alkenyl isoquinolines and bis-isoquinolines were easily attained through this developed chemistry, which can be further used for various organic transformations. Operational simplicity, high atom-economy, broad substrate scope, functional group tolerance and applicability towards large scale synthesis are the advantageous features of this developed methodology.
Cp?-Free Cobalt-Catalyzed C-H Activation/Annulations by Traceless N, O-Bidentate Directing Group: Access to Isoquinolines
Li, Xiao-Cai,Du, Cong,Zhang, He,Niu, Jun-Long,Song, Mao-Ping
supporting information, p. 2863 - 2866 (2019/04/17)
N,O-Bidentate directing-enabled, traceless heterocycle synthesis is described via Cp?-free cobalt-catalyzed C-H activation/annulation. The weakly coordinating nature of the carboxylic acid was employed for the preparation of isoquinolines. Meanwhile, the N-O bond of the α-imino-oxy acid can serve as an internal oxidant. Terminal as well as internal alkynes can be efficiently applied to the catalytic system. This operationally simple approach shows a broad substrate scope with the products obtained in good to excellent yields.
Highly Regioselective Isoquinoline Synthesis via Nickel-Catalyzed Iminoannulation of Alkynes at Room Temperature
Sun, Jian-Guo,Zhang, Xiao-Yu,Yang, Hua,Li, Ping,Zhang, Bo
, p. 4965 - 4969 (2018/09/25)
A simple and cost-efficient nickel catalytic system for the annulation of 2-haloaldimines with alkynes to synthesize 3,4-disubstituted and 3-substituted isoquinolines at room temperature has been developed. The air-stable and inexpensive Ni(dppe)Cl2 was employed as a precatalyst, and Et3N was found to be an essential additive for obtaining high yields. By using this nickel catalytic system one-pot three-component direct synthesis of isoquinolines starting with simple 2-halobenzaldehydes, tert-butylamine, and alkynes were also achieved. These reactions occur in moderate to excellent yields with complete regioselectivity. Moreover, these reactions feature a broad substrate scope, easy scalability, operational simplicity, and excellent practicality.
Ruthenium-Catalyzed Electrochemical Dehydrogenative Alkyne Annulation
Xu, Fan,Li, Yan-Jie,Huang, Chong,Xu, Hai-Chao
, p. 3820 - 3824 (2018/05/22)
A ruthenium-catalyzed electrochemical dehydrogenative annulation reaction of aniline derivatives and alkynes has been developed for the synthesis of indoles. Electric current is used to recycle the active ruthenium-based catalyst and promote H2 evolution. The electrolysis reaction is operationally convenient as it employs a simple undivided cell, proceeds efficiently in an aqueous solution, and is insensitive to air.
Cobalt-Catalyzed Selective Synthesis of Isoquinolines Using Picolinamide as a Traceless Directing Group
Kuai, Changsheng,Wang, Lianhui,Li, Bobin,Yang, Zhenhui,Cui, Xiuling
supporting information, p. 2102 - 2105 (2017/04/27)
Picolinamide has first been employed as a traceless directing group for the cobalt-catalyzed oxidative annulation of benzylamides with alkynes to synthesize isoquinolines through C-H/N-H bonds activation. Oxygen is used as a terminal oxidant. This protocol exhibits good functional group tolerance and excellent regioselectivity. Both terminal and internal alkynes can be efficiently applied to this catalytic system as substrates.
Palladium-catalyzed enolate arylation as a key C-C bond-forming reaction for the synthesis of isoquinolines
Pilgrim, Ben S.,Gatland, Alice E.,Esteves, Carlos H. A.,McTernan, Charlie T.,Jones, Geraint R.,Tatton, Matthew R.,Procopiou, Panayiotis A.,Donohoe, Timothy J.
, p. 1065 - 1090 (2016/01/15)
The palladium-catalyzed coupling of an enolate with an ortho-functionalized aryl halide (an α-arylation) furnishes a protected 1,5-dicarbonyl moiety that can be cyclized to an isoquinoline with a source of ammonia. This fully regioselective synthetic route tolerates a wide range of substituents, including those that give rise to the traditionally difficult to access electron-deficient isoquinoline skeletons. These two synthetic operations can be combined to give a three-component, one-pot isoquinoline synthesis. Alternatively, cyclization of the intermediates with hydroxylamine hydrochloride engenders direct access to isoquinoline N-oxides; and cyclization with methylamine, gives isoquinolinium salts. Significant diversity is available in the substituents at the C4 position in four-component, one-pot couplings, by either trapping the in situ intermediate after α-arylation with carbon or heteroatom-based electrophiles, or by performing an α,α-heterodiarylation to install aryl groups at this position. The α-arylation of nitrile and ester enolates gives access to 3-amino and 3-hydroxyisoquinolines and the α-arylation of tert-butyl cyanoacetate followed by electrophile trapping, decarboxylation and cyclization, C4-functionalized 3-aminoisoquinolines. An oxime directing group can be used to direct a C-H functionalization/bromination, which allows monofunctionalized rather than difunctionalized aryl precursors to be brought through this synthetic route.
C-H activation guided by aromatic N-H ketimines: Synthesis of functionalized isoquinolines using benzyl azides and alkynes
Gupta, Sreya,Han, Junghoon,Kim, Yongjin,Lee, Soon W.,Rhee, Young Ho,Park, Jaiwook
, p. 9094 - 9103 (2014/12/11)
Aromatic N-H ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic N-H ketimines, our protocol works under mild and neutral conditions, which enabled the synthesis of isoquinolines having various functionalities such as carbonyl, ester, alkenyl, and ether groups. In addition, the imidates generated from α-azido ethers were successfully used for the synthesis of 1-alkoxyisoquinolines.
Palladium catalyzed, heteroatom-guided C-H functionalization in the synthesis of substituted isoquinolines and dihydroisoquinolines
Tiwari, Virendra Kumar,Pawar, Govind Goroba,Jena, Himanshu Sekhar,Kapur, Manmohan
supporting information, p. 7322 - 7325 (2014/07/07)
A new approach for the functionalization of C-4 of isoquinolines is reported. The method utilizes palladium catalyzed, hetero-atom guided (or electrophilic metalation) direct arylation via regioselective C-H functionalization of dihydroisoquinolines.
Palladium-catalyzed annulation of internal alkynes in aqueous medium
Ang, Wei Jie,Tai, Chih-Hsuan,Lo, Lee-Chiang,Lam, Yulin
, p. 4921 - 4929 (2014/01/23)
To facilitate precatalyst recovery and reuse, we have developed a fluorous, oxime-based palladacycle 1 and demonstrated that it is a very efficient and versatile precatalyst for carbo- and heteroannulation of internal alkynes with functionalized aryl halides in aqueous medium. A uniform reaction condition for these annulation reactions was also developed.
Efficient copper(I)-catalyzed, microwave-assisted, one-pot synthesis of 3,4-diaryl isoquinolines
Hu, Zhang,Ou, Li-Li,Li, Si-Dong,Yang, Lei
, p. 3461 - 3469 (2015/06/08)
An efficient copper-catalyzed, microwave-assisted, one-pot reaction has been developed for synthesis of 3,4-diaryl isoquinolines. The reaction was performed in two steps via a CuI/2,2′-biimidazole-catalyzed tandem process from N-tert-butyl-o-iodobenzaldim
