- Continuous flow photochemistry as an enabling synthetic technology: Synthesis of substituted-6(5: H)-phenanthridinones for use as poly(ADP-ribose) polymerase inhibitors
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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.
- Fang,Tranmer
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supporting information
p. 720 - 724
(2016/05/19)
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- 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
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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
- Nayak, Susanta K.,Kishore Reddy,Row, Tayur N. Guru,Chopra, Deepak
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experimental part
p. 1578 - 1596
(2012/04/04)
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- Substituted 2-phenyl-4-quinolone-3-carboxylic acid compounds and their use as antitumor agents
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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.
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Page/Page column 7
(2008/06/13)
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- Cyclizations. Part 1. Electrochemical and Photochemical Reactions of 1-(4-Fluorophenyl)-5-(2-halogenophenyl)tetrazoles
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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.
- Donnelly, Shileen,Grimshaw, James,Trocha-Grimshaw, Jadwiga
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p. 1557 - 1562
(2007/10/02)
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