153386-06-2Relevant academic research and scientific papers
Continuous flow photochemistry as an enabling synthetic technology: Synthesis of substituted-6(5: H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors
Fang,Tranmer
supporting information, p. 720 - 724 (2016/05/19)
Methods utilizing continuous flow photochemistry, an enabling synthetic technology, have been developed for the generation of phenanthridinones via an intramolecular photochemical cyclization of 2-chlorobenzamides for the purposes of generating poly(ADP-ribose) polymerase inhibitors. Herein we report 16 examples of a single-step flow photocyclization which produces substituted phenanthridinones in yields up to 99%, while a two-step method leads directly to phenanthridinones from 2-chlorobenzoyl chlorides and anilines via a novel continuous flow amidation/photocyclization protocol. Overall, the flow photocyclization reactions typically progress in good to excellent yields, and in a superior fashion to analogous batch methods, greatly enabling the drug discovery process.
Role of Hetero-halogen (F · · · X, X = Cl, Br, and I) or homo-halogen (X · · · X, X = F, Cl, Br, and I) interactions in substituted benzanilides
Nayak, Susanta K.,Kishore Reddy,Row, Tayur N. Guru,Chopra, Deepak
experimental part, p. 1578 - 1596 (2012/04/04)
A series of halogen-substituted benzanilides have been synthesized and characterized, and crystallization studies directed toward generation of polymorphs have been performed to delineate the importance of interactions involving halogens. The effect of ha
Substituted 2-phenyl-4-quinolone-3-carboxylic acid compounds and their use as antitumor agents
-
Page/Page column 7, (2008/06/13)
Substituted 2-phenyl-4-quinolone-3-carboxylic acid derivatives and their salts were synthesized. The results of preliminary screening revealed that these compounds are potent in killing solid tumor cancers.
Cyclizations. Part 1. Electrochemical and Photochemical Reactions of 1-(4-Fluorophenyl)-5-(2-halogenophenyl)tetrazoles
Donnelly, Shileen,Grimshaw, James,Trocha-Grimshaw, Jadwiga
, p. 1557 - 1562 (2007/10/02)
Electrochemical reduction of the title compounds, where the halogen substituent is Cl, Br or I, leads to cleavage of the carbon-halogen bond to leave a phenyl radical.Competition then follows between intramolecular radical substitution giving 7-fluorotetrazolophenanthridine and further reduction of the radical, then protonation, giving 1-(4-fluorophenyl)-5-phenyltetrazole.Substitution predominates but reduction and protonation becomes a more competing reaction when the halogen is Br or I.Photochemical reaction of the title compounds shows competition between carbon-halogen bond cleavage to give 7-fluorotetrazolophenanthridine and loss of nitrogen followed by cyclization to give 2-halogenophenyl-5-fluorobenzimidazole.Carbon-halogen bond cleavage predominates and becomes the only reaction when the halogen is I.The fluorine substituent allows the determination of product yields by 19F NMR spectroscopy.
