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.).
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.
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.
