87861-97-0Relevant academic research and scientific papers
Rapid construction of C4-substituted phenanthridinones through palladium-catalyzed domino N-arylation/aryl-aryl coupling process
Liu, Chao,Song, Liangliang,Van Meervelt, Luc,Van der Eycken, Erik V.
, (2021/08/05)
An excellent chemo- and regioselective palladium-catalyzed cascade intermolecular N-arylation/aryl-aryl coupling process has been developed. Employing Pd(TFA)2, PCy3?HBF4, K2CO3 and 1,4-dioxane in an oil bath at 100°C for 12 h, diverse C4-substituted phenanthridinones are synthesized from o-bromobenzamides in 42-92% yield. Broad substrate scope and excellent functional group tolerance are observed. The synthetic utility of this method is illustrated by the further derivatization to prepare multiple-substituted phenanthridinones in 30-75% yield.
Base-promoted aerobic oxidation of: N -alkyl iminium salts derived from isoquinolines and related heterocycles
Bai, Li-Gang,Zhou, Yue,Zhuang, Xin,Zhang, Liang,Xue, Jian,Lin, Xiao-Long,Cai, Tian,Luo, Qun-Li
supporting information, p. 197 - 203 (2020/01/13)
Potassium tert-butoxide-promoted aerobic oxidation of N-alkyl iminium salts is reported. The reaction is atom-economical and environmentally friendly. Iminium salts derived from isoquinoline, quinoline, phenanthridine, phenanthroline, and phthalazine were successfully transformed into their corresponding unsaturated lactams with up to 95% yield under mild conditions in the absence of photocatalysts and metallic or organic catalysts. Owing to the general substrate scope, low cost, feasibility of scale up, wide availability of reagents, and green reaction conditions, this method shows great potential for preparing isoquinolones and related compounds. The method was applied for atom- and step-economical total synthesis of natural products such as norketoyobyrine.
NIS-mediated oxidative arene C(sp2)-H amidation toward 3,4-dihydro-2(1H)-quinolinone, phenanthridone, and N-fused spirolactam derivatives
Wu, Lingang,Hao, Yanan,Liu, Yuxiu,Wang, Qingmin
, p. 6762 - 6770 (2019/07/22)
A new radical-mediated intramolecular arene C(sp2)-H amidation of 3-phenylpropanamides or [1,1′-biphenyl]-2-carboxamides was developed to prepare a series of 3,4-dihydro-2(1H)-quinolinone and phenanthridone derivatives in moderate to excellent yields (33-94%). Spirolactams could also be obtained using this protocol.
Carbene-catalyzed aerobic oxidation of isoquinolinium salts: Efficient synthesis of isoquinolinones
Wang, Guanjie,Hu, Wanyao,Hu, Zhouli,Zhang, Yuxia,Yao, Wei,Li, Lin,Fu, Zhenqian,Huang, Wei
supporting information, p. 3302 - 3307 (2018/07/29)
A mild and environmentally friendly carbene-catalyzed aerobic oxidation of isoquinolinium salts was successfully realized. Accordingly, a diverse set of isoquinolinones and phenanthridinones was efficiently prepared in good to excellent yields. The mechanistic study indicates that the formation of an aza-Breslow intermediate is the crucial step in this transformation. This reaction features ambient air as the sole oxidant and oxygen source, a broad substrate scope, and excellent functional-group tolerance and proceeds under mild reaction conditions. Furthermore, a highly efficient synthesis of bioactive molecules and natural products including N-methylcrinasiadine, N-isopentylcrinasiadine, N-phenethylcrinasiadine, isoindolo[2,1-b]isoquinolin-5(7H)-one, PJ-34, rac-Gusanlung D, rosettacin, 8-oxopseudopalmatine and ilicifoline B was accomplished.
Nickel-Catalyzed Denitrogenative Annulation of 1,2,3-Benzotriazin-4-(3H)-ones with Benzynes for Construction of Phenanthridinone Scaffolds
Thorat, Vijaykumar H.,Upadhyay, Nitinkumar Satyadev,Murakami, Masahiro,Cheng, Chien-Hong
, p. 284 - 289 (2017/12/26)
The synthesis of phenanthridinones via denitrogenative annulation of 1,2,3-benzotriazin-4-(3H)-ones with arynes catalysed by Ni(0)/dppm was successfully developed. A variety of phenanthridinones were prepared in good to excellent yields. Based on this method, nature product, N-methylcrinasidine, was synthesized. (Figure presented.).
Palladium-Catalyzed Direct Synthesis of Phenanthridones from Benzamides through Tandem N–H/C–H Arylation
Banerji, Biswadip,Chatterjee, Satadru,Chandrasekhar,Nayan, Chinmay,Killi, Sunil Kumar
, p. 5214 - 5218 (2017/09/29)
We report a palladium-catalyzed method for the direct synthesis of phenanthridones from benzamides in a single step. Unlike previous reports, the current protocol does not need any directing groups or any harsh conditions. This methodology has a wide functional group tolerance therefore a series of phenanthridones were synthesized with a yield up to 87 %. The efficacy of this protocol was further explored by synthesizing some important naturally occurring amaryllidaceae alkaloids in a single step with very good yields.
Pd/Cu-Catalyzed aerobic oxidative aromatic C-H bond activation/N-dealkylative carbonylation towards the synthesis of phenanthridinones
Shi, Renyi,Niu, Huiying,Lu, Lijun,Lei, Aiwen
, p. 1908 - 1911 (2017/02/10)
It is important to achieve diverse functionalization of tertiary anilines due to their importance in biological molecules, pharmaceutical, functional materials, and ligands. A straightforward Pd/Cu-catalyzed oxidative C-H bond activation/N-dealkylative carbonylation of tertiary [1,1′-biphenyl]-2-anilines towards the synthesis of various biologically important phenanthridin-6(5H)-ones has been developed. A wide range of functional groups are well tolerated in this transformation. Moreover, O2 is utilized as the terminal oxidant to promote the oxidative carbonylation process.
Synthesis of phenanthridinones using Cu- or Pd-mediated C[sbnd]N bond formation
Nealmongkol, Prattya,Calmes, Jordan,Ruchirawat, Somsak,Thasana, Nopporn
, p. 735 - 741 (2017/01/16)
The chemoselective synthesis of phenanthridinones was studied using copper(I)- and palladium(II)-catalyzed C[sbnd]N bond formation with various bases, ligands, and solvents. Phenanthridinones were obtained from 2-halobiarylcarboxylates and amines in a one
[N,P]-pyrrole PdCl2 complexes catalyzed the formation of dibenzo-α-pyrone and lactam analogues
Suárez-Meneses,Oukhrib,Gouygou,Urrutigo?ty,Daran,Cordero-Vargas,Ortega-Alfaro,López-Cortés
, p. 9621 - 9630 (2016/07/06)
We herein report the synthesis and catalytic application of a new family of [N,P] ligands based on the pyrrole ring with alpha-phosphine or phosphole units. Their palladium complexes (3a-d) were obtained in very good yields and their catalytic properties were evaluated in the direct intramolecular arylation to obtain both benzopyranones and phenanthridinones. The air stable complex 3a exhibited the best catalytic performance of this series of complexes, using 1 mol% of catalyst in combination with microwaves to promote this reaction.
Collective Synthesis of Phenanthridinone through C-H Activation Involving a Pd-Catalyzed Aryne Multicomponent Reaction
Feng, Minghao,Tang, Bingqing,Xu, Hong-Xi,Jiang, Xuefeng
supporting information, p. 4352 - 4355 (2016/11/01)
A palladium-catalyzed multicomponent reaction (MCR) involving aryne, CO, and aniline is established for straightforward assembly of a phenanthridinone scaffold through C-H bond activation. Free combination with multiple kinds of readily available anilines and arynes is facilely achieved for phenanthridinone construction without prefunctionalization. Representative natural products were subsequently synthesized through this MCR strategy highly efficiently. Control experiments and interval NMR tracking revealed the mechanism, particularly the key role of CuF2 in determining the aryne-releasing rate from the precursor in this transformation.
