1015-89-0Relevant academic research and scientific papers
MeOTf- and TBD-Mediated Carbonylation of ortho-Arylanilines with CO2 Leading to Phenanthridinones
Wang, Sheng,Shao, Peng,Du, Gaixia,Xi, Chanjuan
, p. 6672 - 6676 (2016)
Carbonylation of o-arylanilines utilizing CO2 as a carbonyl source for the synthesis of important phenanthridinones with a free (NH)-lactam motif has been described under metal-free condition. A range of o-arylanilines were transformed to the corresponding phenanthridinones in high yields.
Oxygen as oxidant in palladium-catalyzed inter- and intramolecular coupling reactions
Hagelin, Helena,Oslob, Johan D.,Akermark, Bjoern
, p. 2413 - 2416 (1999)
Facile palladium-catalyzed cyclizations of arylaminoquinones giving biologically important carbazoloquinones in high yields have been performed with oxygen as the single oxidant. By a slight modification of the catalyst, diphenylamine, diphenyl ether, and related compounds can be cyclized. The system could also be used in intermolecular couplings between naphthoquinones and benzene or naphthalene.
Radical Borylative Cyclization of Isocyanoarenes with N-Heterocyclic Carbene Borane: Synthesis of Borylated Aza-arenes
Liu, Yao,Li, Ji-Lin,Liu, Xu-Ge,Wu, Jia-Qiang,Huang, Zhi-Shu,Li, Qingjiang,Wang, Honggen
, p. 1891 - 1897 (2021)
Borylated aza-arenes are of great importance in the area of organic synthesis. A radical borylative cyclization of isocyanoarenes with N-heterocyclic carbene borane (NHC-BH3) under metal-free conditions was developed. The reaction allows the efficient assembly of several types of borylated aza-arenes (phenanthridines, benzothiazoles, etc.), which are difficult to access using alternative methods. Mild reaction conditions, a good functional-group tolerance, and generally good efficiencies were observed. The utility of these products is demonstrated, and the mechanism is discussed.
Copper-catalyzed intramolecular C–N coupling reaction of aryl halide with amide
Chen, Wei-Lin,Jhang, Yuan-Ye,Hsieh, Jen-Chieh
, p. 3517 - 3526 (2017)
An efficient and concise method for the ligand-free copper-catalyzed intramolecular C–N bond coupling was developed, which afforded various (NH)-phenanthridinones in good to excellent yields with tolerance of various substrates.
RADICALOID INTERMEDIATES IN THE PHOTOCHEMISTRY OF 6-CYANOPHENATHRIDINE N-OXIDE
Albini, Angelo,Pasani, Elisa,Buchardt, Ole
, p. 4849 - 4852 (1982)
Irradiation of 6-cyanophenanthridine N-oxide in presence of 2,3-dimethyl-2-butene resulted in a novel type of photoaddition with rearrangement to give 2-cyano-8,8,9,9-tetramethyl--dibenzo-1,3-oxazonin and 6-(2-cyano-1,1,2-trimethylpropyloxy)phenanthridine as a minor product, which is regarded as strong evidence for an initial photochemical generation of a biradical, and not an oxaziridine as previously suggested.
Reactivity of cyclopalladated compounds derived from biphenyl-2-ylamine towards carbon monoxide, tbutyl isocyanide and alkynes
Albert, Joan,D'Andrea, Luci?a,Granell, Jaume,Zafrilla, Javier,Font-Bardia, Mercè,Solans, Xavier
, p. 4895 - 4902 (2007)
The reactivity of the dimeric cyclopalladated compounds derived from biphenyl-2-ylamine (μ-X)2[κ2-N2′,C1-1-Pd-2-{(2′-NH2C6H4)C6H4}]2 [X = OAc (1), X = Cl (2)] towards unsaturated organic molecules is reported. Compound 1 reacted with carbon monoxide and tbutyl isocyanide producing phenanthridin-6(5H)-one and N-tert-butylphenanthridin-6-amine in 63% and 88% yield, respectively. Compound 2 reacted separately with diphenylacetylene and 3-hexyne, affording the mononuclear organopalladium compounds [κ2-N2″,C1-η2-C2,C3- 1-Pd{(R-C{double bond, long}C-R)2-2′-(2″-NH2C6H4)C6H4}Cl] [R = Ph (5), R = Et (6)] in 50-60% yield, which derived from the insertion of two alkyne molecules into the C-Pd σ bonds of 2. The crystal structure of compounds 5 and 6 has been determined. Compound 5 crystallized in the monoclinic space group P21/n with a = 13.3290(10) A?, b = 10.6610(10) A? and c = 22.3930(10) A? and β = 100.2690(10)°. Compound 6 crystallized in the triclinic space group P over(1, ?) with a = 7.271(7) A?, b = 10.038(3) A? and c = 16.012(5) A?, and α = 106.79(3)°, β = 96.25(4)° and γ = 99.62(4)°. The crystal structures of 5 and 6 have short intermolecular Pd-Cl?H-N-Pd non-conventional hydrogen bonds, which associated the molecules in chains in the first case and in dimers in the second.
Synthesis of 5(6H)-phenanthridones using Diels-Alder reaction of 3-nitro-2(1H)-quinolones acting as dienophiles
Fujita, Reiko,Yoshisuji, Toshiteru,Wakayanagi, Sota,Wakamatsu, Hideaki,Matsuzaki, Hisao
, p. 204 - 208 (2006)
Diels-Alder reactions of 3-nitro-2(1H)-quinolones with 1,3-butadiene derivatives were carried out to give the phenanthridone derivatives under both atmospheric and high pressure conditions. Furthermore, the reactivity of 3-substituted 2(1H)-quinolones acting as a dienophile with 2,3-dimethyl-1,3- butadiene was examined using molecular orbital (MO) calculation.
Electrochemical Formation of N-Acyloxy Amidyl Radicals and Their Application: Regioselective Intramolecular Amination of sp2 and sp3 C-H Bonds
Zhang, Sheng,Li, Lijun,Xue, Mengyu,Zhang, Ruike,Xu, Kun,Zeng, Chengchu
, p. 3443 - 3446 (2018)
Electrochemical generation of N-acyloxy amidyl radicals via an inner-sphere electron-transfer process is described for the first time. With NaBr as the catalyst and electrolyte, the in situ generated amidyl radicals undergo intramolecular C(sp2/sp3)-H aminations to give lactams with unprecedented regio- and chemoselectivities. Moreover, the synthetic utility of current method is demonstrated by the synthesis of PJ34 and Phenaglaydon.
Annulation of Benzamides with Arynes Using Palladium with Photoredox Dual Catalysis
Zhao, Jie,Li, Hongji,Li, Pinhua,Wang, Lei
, p. 9007 - 9016 (2019)
Efficient annulation of benzamides with arynes using palladium and photoredox dual catalysis under an oxygen atmosphere is disclosed, which circumvents the use of external toxic metal oxidant and proceeds readily via aryne insertion at room temperature to construct the phenanthridinone backbone.
Dual Mechanisms for the Fragmentation of 1-Benzoylbenzotriazole upon Electron Impact
Yamada, Shuzo,Kamiyama, Yojiro,Ohashi, Mamoru
, p. 1 - 3 (1980)
The electron impact induced fragmentation of 1-benzoylbenzotriazole has been studied by 13C labelling experiments.It has been found that the loss of CO from the 2>+. ions proceeds by two routes; about 78percent of the ions decompose via the molecular ions of the corresponding thermal fragmentation product, 2-phenylbenzoxazole, and 22percent via those of the corresponding photochemical fragmentation product, 6-phenanthridone.
