102024-05-5Relevant articles and documents
Metal-Free, Visible-Light Promoted Intramolecular Azole C?H Bond Amination Using Catalytic Amount of I2: A Route to 1,2,3-Triazolo[1,5-a]quinazolin-5(4H)-ones
Du, Weigen,Huang, Hongtai,Xiao, Tiebo,Jiang, Yubo
, p. 5124 - 5129 (2020)
A metal-free, visible-light promoted intramolecular azole C?H bond amination for the rapid and efficient synthesis of pharmaceutical important 1,2,3-triazolo[1,5-a]quinazolin-5(4H)-ones has been developed. Employing 2-(1,2,3-triazol-1-yl)benzamides as the easily available precursors and catalytic amount of I2 as an initiator, the desired product were isolated in moderate to excellent yiels with a broad substrate scope and good functional group tolerance. Furthermore, this protocol features mild conditions, operational simplicity, and easy scale-up. Preliminary mechanistic studies suggested that a radical pathway might be involved during the reaction. (Figure presented.).
Transition-Metal-Free Synthesis of Phenanthridinones through Visible-Light-Driven Oxidative C–H Amidation
Usami, Kaoru,Yamaguchi, Eiji,Tada, Norihiro,Itoh, Akichika
, p. 1496 - 1504 (2019/06/27)
The treatment of N-aryl biphenylcarboxamide, 1-chloroanthraquinone (1-Cl-AQN) catalyst, and K2CO3 in CHCl3 under visible light irradiation affords phenanthridinone via radical cyclization. This reaction proceeds under transition-metal-free condition, room temperature, and direct C–H amidation. Mechanistic studies indicate that amidyl radical generation proceeds by visible light induced proton coupled electron transfer (PCET) from N–H bond of the amide.
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.
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.).
Visible-Light-Photocatalyzed Synthesis of Phenanthridinones and Quinolinones via Direct Oxidative C-H Amidation
Moon, Yonghoon,Jang, Eunyoung,Choi, Soyeon,Hong, Sungwoo
supporting information, p. 240 - 243 (2018/01/17)
A straightforward synthetic strategy to construct biologically relevant phenanthridinones and quinolinones was developed via visible-light-promoted direct oxidative C-H amidation. In this photocatalytic system, amidyl radicals can be generated by homolysis of the N-H bond of simple amide precursors via single-electron transfer under blue LED illumination, which leads to oxidative intramolecular C-H amidation. Moreover, an efficient synthetic strategy using a photocascade enabled facile assembly of quinolinone structures through a catalytic sequence involving triplet energy (ET) transfer-based E/Z olefin isomerization and subsequent photocatalytic generation of amidyl radical intermediates.
Practical Synthesis of Phenanthridinones by Palladium-Catalyzed One-Pot C-C and C-N Coupling Reaction: Extending the Substrate Scope to o-Chlorobenzamides
Liu, Hailong,Han, Weibiao,Li, Chun,Ma, Zhiyong,Li, Ruixiang,Zheng, Xueli,Fu, Haiyan,Chen, Hua
, p. 389 - 393 (2016/02/18)
A highly efficient construction of phenanthridinone derivatives from o-halobenzamides was developed by using a phosphine-free palladium catalyst in N,N-dimethylacetamide. The domino reaction proceeds through a sequential C-C and C-N bond-formation process in one pot. This protocol exhibits broad substrate scope and affords a series of phenanthridinones in up to 93 % yield. Importantly, the protocol could also be applied for the less reactive o-chlorobenzamides. The approach constitutes the first example of the synthesis of phenanthridinones from this kind of substrate. Moreover, the success of a gram-scale reaction demonstrated that this operationally simple process is scalable.
Palladium-catalyzed annulation of benzynes with N-substituted-N-(2- halophenyl)formamides: Synthesis of phenanthridinones
Yang, Yuan,Huang, Hui,Wu, Lijun,Liang, Yun
, p. 5351 - 5355 (2014/07/21)
A novel and efficient procedure for the synthesis of N-substituted phenanthridinones via palladium-catalyzed annulation of benzynes with N-substituted-N-(2-halophenyl)formamides has been developed. This methodology constructs two new C-C bonds via an arylation/annulation process, and provides the desired products in good yields. This journal is the Partner Organisations 2014.
